smitathkr1/organic_reactions_structured · Datasets at Hugging Face

name stringlengths 1 52	url stringlengths 31 118	reactants listlengths 0 3	reagents listlengths 0 3	products listlengths 0 2	byproducts listlengths 0 2	conditions stringclasses 14 values	description stringclasses 76 values
appel-reaction	https://www.name-reaction.com/appel-reaction	[ "alcohol", "ROH" ]	[ "triphenylphosphine", "PPh3", "tetrahalomethane" ]	[ "alkyl halide", "RCl" ]	[ "triphenylphosphine oxide", "Ph3P=O" ]		The Appel reaction is an organic reaction used to convert an alcohol to an alkyl halide using a tetrahalomethane and triphenylphosphine. The reaction begins with the halogenation of triphenyl-phosphine followed by the formation of the alkoxide from the alcohol starting material. The alkoxide subsequently attacks the phosphorous, releasing the halide leaving group. In a nucleophilic substitution reaction (SN2), the halide (nucleophile) attacks the carbon stereocenter resulting in the the final alkyl halide product with inverted stereochemistry. Triphenylphosphine oxide is a byproduct of this reaction and the formation of the strong P=O double bond is a driving force for this reaction.[1]
baeyer-villiger-oxidation	https://www.name-reaction.com/baeyer-villiger-oxidation	[ "carbonyl compound" ]	[ "acid catalyst" ]	[ "ester" ]	[]	acid	The Baeyer-Villiger oxidation is an organic reaction used to convert a ketone to an ester using a peroxyacid (such as mCPBA). The reaction of the ketone with the acid results in a tetrahedral intermediate, with an alkyl migration following to release a carboxylic acid. The more electron rich R group migrates to the oxygen in this concerted process, allowing for accurate prediction of the stereochemistry of the product.[1]
bartoli-indole-synthesis	https://www.name-reaction.com/bartoli-indole-synthesis	[ "carbonyl compound" ]	[ "acid catalyst", "organometallic reagent" ]	[]	[]	acid	The Bartoli indole synthesis is an organic reaction where a substituted nitroarene is converted to an indole using an excess of a vinyl Grignard reagent followed by an acid work-up. The substituents on the nitroarene affect the yield of this reaction where the highest yields are observed for ortho substituted reagents and the bulkier groups usually result in higher yields. The Bartoli indole synthesis mechanism begins with a series of attacks on the nitroarene regent by the Grigrand reagents and is then followed by a 3,3 sigmatropic rearrangement (Claisen) step which results in an aldehyde intermediate. The aldehyde is then quickly attacked by the nearby nitrogen intramolecularly and a subsequent attack by the third equivalent of the Grignard reagent restored aromaticity. A final acid work-up step affords the indole product.[1][2]
baylis-hillman-reaction	https://www.name-reaction.com/baylis-hillman-reaction	[ "carbonyl compound" ]	[ "base catalyst", "organometallic reagent" ]	[]	[]	catalyst	The Baylis-Hillman reaction is an organic reaction used to form a C-C bond between an α-β unsaturated carbonyl compound and an aldehyde, activated ketone, or other carbon electrophiles. This reaction is most commonly catalyzed by DABCO but other tertiary amines or phosphines can also be used as catalysts. The catalyst activates the conjugated carbonyl compound to form a stabilized nucleophilic anion which subsequently attacks the electrophile. The reaction proceeds to afford the final product and regenerate the catalyst.[1]
beckmann-rearrangement	https://www.name-reaction.com/beckmann-rearrangement	[ "alcohol", "carbonyl compound" ]	[ "acid catalyst", "alcohol" ]	[ "amide" ]	[]		The Beckmann rearrangement is an organic reaction used to convert an oxime to an amide under acidic conditions. The reaction begins by protonation of the alcohol group forming a better leaving group. The R grouptransto the leaving group then migrates to the nitrogen, resulting in a carbocation and the release of a water molecule. Thistrans[1-2]-shift allows for the prediction of the regiochemistry of this reaction. The water molecule then attacks the carbocation and after deprotonation and tautomerization results in the final amide product.[1]
biginelli-reaction	https://www.name-reaction.com/biginelli-reaction	[ "alcohol", "carbonyl compound" ]	[ "acid catalyst", "alcohol" ]	[ "amide", "ester" ]	[]	acid	The Biginelli reaction is a one-pot three-component organic reaction between a β-keto ester, an aryl aldehyde, and urea to produce pyrimidones under acidic conditions. This reaction begins with protonation of the aldehyde by the acid and is followed by attack of the amine from urea. Proton transfer steps then result in a protonated alcohol which leaves as water to form an N-acyliminium ion intermediate. The intermediated is then attacked by the enol form of the β-keto ester. Reaction of the other amine group to the carbonyl produces a cyclic intermediate. Proton transfer steps, the release of water, and deprotonation result in the final pyrimidone product.[1][2]
birch-reduction	https://www.name-reaction.com/birch-reduction	[ "alcohol" ]	[ "alcohol" ]	[]	[]		The Birch reduction is an organic reaction where aromatic rings undergo a 1,4-reduction to provide unconjugated cyclohexadienes. The reduction is conducted by sodium or lithium metal in liquid ammonia and in the presence of an alcohol. The mechanism begins with a single electron transfer(SET) from the metal to the aromatic ring, forming a radical anion. The anion then picks up a proton from the alcohol which results in a neutral radical intermediate. Another SET, and abstraction of a proton from the alcohol results in the final cyclohexadiene product and two equivalents of metal alkoxide salt as a byproduct. In the case of substituted aromatic rings, the regiochemistry can be predicted using Birch's empirical rules.[1]
buchwald-hartwig-amination	https://www.name-reaction.com/buchwald-hartwig-amination	[]	[ "base catalyst" ]	[ "amide" ]	[]	catalyst base	The Buchwald-Hartwig amination is an organic reaction used to make carbon-nitrogen bonds. This is essentially a cross-coupling reaction of an aryl halide with an amine using palladium as a catalyst and a strong base. The reaction begins by oxidative addition of the aryl halide to the palladium which is followed by coordination of the amine to the palladium. The strong base then abstracts a proton from the amine, forming an amide, which in turn attacks the palladium and kicks out the halide as a leaving group. Reductive elimination then produces the final aryl amine product and regenerates the catalyst.[1][2]
cannizzaro-reaction	https://www.name-reaction.com/cannizzaro-reaction	[ "alcohol", "carbonyl compound" ]	[ "base catalyst", "acid catalyst", "alcohol" ]	[ "ester" ]	[]	acid base	The Cannizzaro reaction is a redox reaction in which two molecules of an aldehyde are reacted to produce a primary alcohol and a carboxylic acid using a hydroxide base. The reaction begins with hydroxide attack on the carbonyl carbon followed by deprotonation to give a dianion. This unstable intermediate releases a hydride anion which attacks another molecule of aldehyde. In this process the dianion converts to a carboxylate anion and the aldehyde to an alkoxide. The alkoxide then picks up a proton from water to provide the alcohol final product, while the caboxylate is converted to the carboxylic acid product after acid work-up.[1]
claisen-condensation	https://www.name-reaction.com/claisen-condensation	[ "alcohol", "carbonyl compound" ]	[ "base catalyst", "alcohol" ]	[ "ester" ]	[]	solvent base	The Claisen condensation is an organic reaction used to form a carbon-carbon bond between two ester molecules using an alkoxide base in alcohol to make a β-keto ester. The R group of the ester starting material, the alkoxide base, and the alcohol solvent are chosen to be the same to not end up with a mixture of products. The ester starting material must have an α-hydrogen which is abstracted by the base to form an enolate and alcohol. The enolate then attacks the carbonyl carbon of another ester molecule, an OR group is released to regenerate the base, and the final β-keto ester product is formed. The intramolecular form of the Claisen condensation is theDieckmann condensation.[1]
claisen-rearrangement	https://www.name-reaction.com/claisen-rearrangement	[ "alcohol", "carbonyl compound" ]	[ "acid catalyst" ]	[]	[]	acid heat	The Claisen rearrangement is an organic reaction where an allyl vinyl ether is converted into a γ,δ-unsaturated carbonyl compound with the input of heat or a Lewis acid. This reaction belongs to a class of reactions termed "sigmatropic rearrangements" and it is a concerted process where bonds are forming and breaking at the same time. When substituents are present in the allyl vinyl ether starting material, the stereochemistry of this reaction can be predicted by drawing the molecule in a chair-like conformation and placing the substituents in the equatorial position to minimize the steric interactions.[1][2]
clemmensen-reduction	https://www.name-reaction.com/clemmensen-reduction	[ "carbonyl compound" ]	[ "acid catalyst" ]	[]	[]	acid	The Clemmensen reduction is an organic reaction used to reduce an aldehyde or ketone to an alkane using amalgamated zinc and hydrochloric acid. The mechanism for the Clemmensen reduction is not yet fully understood and there are two popular proposals. The "Carbanionic mechanism", where the zinc attacks the protonated carbonyl directly, and the "Carbenoid mechanism", which is a radical process and the reduction happens on the surface of the zinc metal.[1][2][3]
cope-rearrangement	https://www.name-reaction.com/cope-rearrangement	[ "is", "an" ]	[ "to", "of" ]	[ "it", "at" ]	[]		The Cope rearrangement is an organic reaction where a 1,5-diene, under thermal conditions, is converted to another 1,5-diene structural isomer. This reaction belongs to a class of reactions termed "sigma tropic rearrangements" and it is a concerted process where bonds are forming and breaking at the same time. When substituents are present in the initial diene starting material, the stereochemistry of this reaction can be predicted by drawing the molecule in a chair-like conformation. Placing the substituents in the equatorial position minimizes the steric interactions and leads to the major product. The Cope rearrangement is an equilibrium reaction and the equilibrium position is determined by the overall stability of the starting material and product.[1]
corey-kim-oxidation	https://www.name-reaction.com/corey-kim-oxidation	[ "alcohol", "carbonyl compound" ]	[ "alcohol" ]	[]	[]		The Corey-Kim oxidation is an organic reaction used to convert an alcohol to an aldehyde or ketone using N-chlorosuccinimide (NCS), dimethylsulfide (DMS) and triethylamine (TEA). The mechanism begins with the reaction of DMS with NCS to afford S,S-dimethylsuccinimidosulfonium chloride, also known as "Corey-Kim reagent". This electrophilic reagent is then attacked by the nucleophilic oxygen of the alcohol to form a S-O bond. The addition of TEA results in deprotonation of one of the methyl groups to form a zwitterionic species that undergoes a rearrangement reaction to release DMS gas and provide the final product.[1]
curtius-rearrangement	https://www.name-reaction.com/curtius-rearrangement	[ "as", "is" ]	[ "an", "to" ]	[ "of", "gas" ]	[]		The Curtius rearrangement is an organic reaction used to convert an acyl azide to an isocyanate under thermal conditions. The mechanism consists of an alkyl shift of the R group from the carbonyl carbon to the closest nitrogen with the release of nitrogen gas. The release of gas drives the reaction forward and results in the formation of the isocyanate product which can potentially react further in the presence of nucleophiles in solution.[1][2][3]
dakin-west-reaction	https://www.name-reaction.com/dakin-west-reaction	[ "carbonyl compound" ]	[ "base catalyst", "acid catalyst" ]	[]	[]	acid base	The Dakin-West reaction is an organic reaction used to convert an amino acid and an anhydride to an acylamino ketone using a base and thermal conditions. The reaction begins with acylation of the amino acid on both terminals, first on the amine group, and then on the carboxylic acid group. An intramolecular reaction then follows to give a lactone intermediate. A series of addition and elimination steps and the release of carbon dioxide gas provide the acylamino ketone product.[1][2][3]
dieckmann-condensation	https://www.name-reaction.com/dieckmann-condensation	[ "alcohol", "carbonyl compound" ]	[ "base catalyst", "acid catalyst", "alcohol" ]	[ "ester" ]	[]	acid base	The Dieckmann condensation is an organic reaction used to form a carbon-carbon bond between two tethered ester groups using an alkoxide base in alcohol to make a cyclic β-keto ester. This reaction is essentially an intramolecular form of theClaisen condensation. One ester group of the starting material must have an α-hydrogen which is abstracted by the base to form an enolate and alcohol. The enolate then attacks the carbonyl carbon of another ester molecule, an OR group is released to regenerate the base, and the final β-keto ester product is formed. The product in base is then deprotonated again to form another enolate intermediate and acid-workup is required to isolate the final cyclic β-keto ester product.[1]
diels-alder-reaction	https://www.name-reaction.com/diels-alder-reaction	[]	[]	[ "alkene" ]	[]		The Diels-Alder reaction is an organic reaction used to convert a conjugated diene and a dienophile to a cyclic olefin under thermal conditions. This is a concerted process where bonds are forming and breaking at the same time and the reaction belongs to a class of reactions termed "cycloaddition". The Diels-Alder reaction is by far the most famous 'name reaction' and it is extensively used in natural product synthesis. When predicting the regiochemistry and stereochemistry of the product, things to consider are the electronic character of the substitutes on the diene and dienophile, the partial charges formed, and the orientation of the starting materials when they approach each other.[1][2][3]
eschenmoser-claisen-rearrangement	https://www.name-reaction.com/eschenmoser-claisen-rearrangement	[ "alcohol" ]	[ "alcohol" ]	[ "amide" ]	[]		The Eschenmoser-Claisen rearrangement is an organic reaction where an allylic alcohol is heated with N,N-dimethylacetamide dimethyl acetal to produce a γ,δ-unsaturated amide. The reactions begins with the release of a methoxide group from the amide starting material to produce an iminium cation which is then attacked by the alcohol. Proton transfer steps then follow which place the proton on the remaining methoxide group which is then released as a molecule of methanol and another iminium cation is formed. Deprotonation with methoxide produces a 1,5 diene intermediate which undergoes a Claisen sigmatropic rearrangement to provide the final γ,δ-unsaturated amide product.[1]
eschweiler-clarke-reaction	https://www.name-reaction.com/eschweiler-clarke-reaction	[ "carbonyl compound" ]	[ "acid catalyst" ]	[]	[]	acid	The Eschweiler-Clarke reaction is an organic reaction used to convert a primary or secondary amine to a tertiary amine using formaldehyde and formic acid. This is essentially an amine methylation process which begins with the reaction of the amine starting material with the protonated formaldehyde to provide an intermediate iminium ion. The iminium ion then reacts with the formic acid to give a methylated ammonium ion and release carbon dioxide gas which drives the process forward. Deprotonation of the ammonium ion affords the final methylated amine product. In the case of primary amine starting materials, these steps repeat twice to give the tertiary amine final product.[1][2]
finkelstein-reaction	https://www.name-reaction.com/finkelstein-reaction	[ "alkyl halide", "halide" ]	[ "is", "an" ]	[ "by", "it" ]	[]		The Finkelstein reaction is an organic reaction where an alkyl halide is converted into another alkyl halide by reacting with a metal halide salt. This is an equilibrium process and it is driven forward by taking advantage of the poor solubility in acetone of the newly formed metal halide salt (Le Chatelier's principle). The mechanism for this reaction is a simple, single-step bimolecular nucleophilic substitution reaction (SN2) which like all SN2 reactions occur with inversion of stereochemistry.[1]
fischer-esterification	https://www.name-reaction.com/fischer-esterification	[ "alcohol", "carbonyl compound" ]	[ "base catalyst", "acid catalyst", "alcohol" ]	[ "ester" ]	[]	acid catalyst	The Fischer esterification is an organic reaction used to convert a carboxylic acid and an alcohol to an ester using an acid catalyst. The mechanism begins with protonation of the carbonyl group of the carboxylic acid, which is then attacked by the alcohol. Proton transfer and the subsequent release of water result in an oxonium ion intermediate. A final deprotonation step provides the ester product.[1]
fischer-indole-synthesis	https://www.name-reaction.com/fischer-indole-synthesis	[ "carbonyl compound" ]	[ "base catalyst", "acid catalyst" ]	[]	[]	acid catalyst	The Fischer indole synthesis is an organic reaction used to convert a phenyl hydrazine and an aldehyde or ketone to an indole using an acid catalyst. The mechanism begins with formation of a phenylhydrazone through the acid catalyzed reaction of the hydrazine with the carbonyl. The phenylhydrazone then rearranges to the enamine and gets protonated on the phenyl nitrogen. An "ene reaction" (3,3-sigmatropic rearrangement) ensues, resulting in a diimine and loss of aromaticity. Additional key steps include rearomatization, formation of a cyclic aminal, and the expulsion of ammonia to give the indole product.[1][2]
friedel-crafts-acylation	https://www.name-reaction.com/friedel-crafts-acylation	[ "carbonyl compound" ]	[ "base catalyst", "acid catalyst" ]	[ "ester" ]	[]	acid catalyst	The Friedel-Crafts acylation is an organic reaction used to convert an aryl compound and an acyl halide or anhydride to an aryl ketone using a Lewis acid catalyst (such as AlCl3). The reaction begins with the Lewis acid abstracting the halide (or carboxylate) from the acyl halide (or ester) to form an electrophilic acylium cation and a tetrasubstituted aluminum anion. The aromatic compound then attacks the acylium ion via an electrophilic aromatic substitution (SEAr) to give a cationic product with loss of aromaticity. Deprotonation with the aluminum anion results in the final aryl ketone and regeneration of the Lewis acid catalyst.[1]
friedel-crafts-alkylation	https://www.name-reaction.com/friedel-crafts-alkylation	[ "carbonyl compound" ]	[ "base catalyst", "acid catalyst" ]	[]	[]	acid catalyst	The Friedel-Crafts alkylation is an organic reaction used to convert an aryl compound and an alkyl halide to a substituted aromatic compound using a Lewis acid catalyst (such as AlCl3). The reaction begins with the Lewis acid abstracting the halide from the alkyl halide to form an electrophilic alkyl cation and a tetrasubstituted aluminum anion. The aromatic compound then attacks the alkyl cation via an electrophilic aromatic substitution (SEAr) to give a cationic product with loss of aromaticity. Deprotonation with the aluminum anion results in the final aromatic product and regeneration of the Lewis acid catalyst.[1]
fries-rearrangement	https://www.name-reaction.com/fries-rearrangement	[ "carbonyl compound" ]	[ "base catalyst", "acid catalyst" ]	[ "ester" ]	[]	acid catalyst	The Fries rearrangement is an organic reaction used to convert a phenyl ester to an ortho- and para-hydroxy aryl ketone using a Lewis acid catalyst and Brønsted acid work-up. The mechanism begins with coordination of the ester to the Lewis acid, followed by a rearrangement which generates an electrophilic acylium cation. The aromatic compound then attacks the alkyl cation (both the ortho and para attack are allowed) via an electrophilic aromatic substitution (SEAr). Deprotonation to regenerate aromaticity and Brønsted acid work-up to regenerate the Lewis acid catalyst provide the two hydroxy aryl ketone products.[1][2]
gabriel-synthesis	https://www.name-reaction.com/gabriel-synthesis	[ "carbonyl compound" ]	[ "base catalyst", "acid catalyst" ]	[]	[]	acid base	The Gabriel synthesis is an organic reaction used to convert an alkyl halide to a primary amine using phthalimide with base and followed by hydrazine. The reaction begins with the deprotonation of the phthalimide which then attacks the alkyl halide in an SN2 fashion to give an N-alkylphthalimide intermediate. The intermediate is then cleaved by hydrazine in a series of steps that end with the liberation of the final primary amine product and phthalhydrazide by-product.[1]
grignard-reaction	https://www.name-reaction.com/grignard-reaction	[ "alkyl halide", "R-X" ]	[ "magnesium", "Mg" ]	[ "grignard reagent", "RMgX" ]	[]	acid	The Grignard reaction is an organic reaction used to create a variety of products through the reaction of an organomagnesium compound, also known as a "Grignard reagent" with an electrophile, followed by acid work-up. The Grignard reagent is formed through the reaction of an alkyl or aryl halide with magnesium metal via a radical mechanism. The mechanism of the subsequent reaction of the Grignard reagent with the electrophile is debatable. The most popular proposals are a "concerted mechanism" or another "radical mechanism", both can explain the final addition product.[1][2]
heck-reaction	https://www.name-reaction.com/heck-reaction	[ "unsaturated compound" ]	[ "base catalyst" ]	[ "alkene" ]	[]	Base catalyst base	The Heck reaction is a cross-coupling reaction of an organohalide with an alkene to make a substituted alkene using palladium as a catalyst and a base. The reaction begins by oxidative addition of the aryl halide to the palladium, which is followed by coordination and migratory insertion of the olefin to the palladium. Bond rotation then places the two groups trans to each other to relieve the steric strain and subsequent β-hydride elimination results in a trans final product. Base mediated reductive elimination regenerates the palladium(0) catalyst.[1][2][3]
hell-volhard-zelinsky-reaction	https://www.name-reaction.com/hell-volhard-zelinsky-reaction	[ "carbonyl compound" ]	[ "base catalyst", "acid catalyst" ]	[ "ester" ]	[]	acid catalyst	The Hell-Volhard-Zelinsky reaction is an organic reaction used to convert a carboxylic acid with an α-hydrogen and a halogen, to an α-halo carboxylic acid, using a phosphorous catalyst and water. The mechanism begins with the reaction of the carbonyl oxygen with phosphorous trihalide to form a P–O bond and release a halide anion. The halide then attacks the carbonyl to form an intermediate which rearranges to release an acyl chloride, an acid molecule, and a phosphine oxide. The acyl chloride then tautomerizes to the enol form which subsequently attacks the halogen molecule to form an α-halo acyl halide. Water hydrolysis yields the final α-halo carboxylic acid product.[1][2][3]
henry-reaction	https://www.name-reaction.com/henry-reaction	[ "alcohol", "carbonyl compound" ]	[ "base catalyst", "acid catalyst", "organometallic reagent" ]	[]	[]	acid catalyst base	The Henry reaction is an organic reaction used to convert a nitroalkane with an α-hydrogen and an aldehyde or ketone to a β-nitro alcohol using a base catalyst. The mechanism begins with deprotonation of the nitroalkane by the base to give a resonance stabilize anionic intermediate which subsequently attacks the carbonyl compound to form an alkoxide. The alkoxide then picks up a proton from the conjugate acid of the base (H2O in this case) to give the final β-nitro alcohol product and regenerate the base catalyst.[1]
hofmann-elimination	https://www.name-reaction.com/hofmann-elimination	[ "unsaturated compound" ]	[ "base catalyst" ]	[ "alkene" ]	[]		The Hofmann elimination is an organic reaction used to convert an amine with a β-hydrogen to an alkene using methyl iodide, silver oxide and water under thermal conditions. The mechanism begins with an attack of the amine on methyl iodide to form an ammonium iodide salt. The iodide then reacts with silver oxide to form silver iodide which is insoluble and precipitates out of solution and a silver oxide ion which deproto-nates water to form a hydroxide ion. Heating the mixture facilitates an elimination reaction where the hydroxide picks up the β-hydrogen from the ammonium ion and releases an amine to afford the final olefin product.[1][2]
hofmann-rearrangement	https://www.name-reaction.com/hofmann-rearrangement	[]	[ "base catalyst" ]	[ "amide", "ester" ]	[]	heat base	The Hofmann rearrangement is an organic reaction used to convert a primary amide to a primary amine using a halogen, base, water, and heat. The reaction begins with deprotonation of the amide by the base to form an anion which then attacks the halogen to form a N-haloamide. A second deprotonation by the base provides an anion that rearranges to an isocyanate intermediate and releases a halide anion. The isocyanate is then attacked by water which after a series of proton transfer step results in a zwitterionic intermediate, containing an ammonium cation and a carboxylate anion. Thermal conditions result in the explosion of carbon dioxide gas and quenching of the ammonium cation to the amine product.[1]
ireland-claisen-rearrangement	https://www.name-reaction.com/ireland-claisen-rearrangement	[ "carbonyl compound" ]	[ "base catalyst", "acid catalyst" ]	[ "ester", "alkene" ]	[]	acid base	The Ireland-Claisen rearrangement is an organic reaction used to convert an allyl ester to a γ,δ-unsaturated carboxyl acid using LDA, TMSCl, and NaOH/H2O. The reaction begins with deprotonation of the α-hydrogen of the ester to form an enolate which then attacks TMSCl to stabilize the charge and produce LiCl salt. The two olefin groups are ideally positioned for aClaisen rearrangement, which results in the formation of a carbonyl group. Deprotection of the TMS group with base and protonation then results in the final carboxylic acid product.[1][2][3]
johnson-claisen-rearrangement	https://www.name-reaction.com/johnson-claisen-rearrangement	[ "alcohol", "carbonyl compound" ]	[ "acid catalyst", "alcohol" ]	[ "ester", "alkene" ]	[]		The Johnson-Claisen rearrangement is an organic reaction where an allylic alcohol is heated with trialkyl orthoacetate under midly acidic conditions to produce a γ,δ-unsaturated ester. The reaction begins with protonation of one of the alkoxide groups of the orthoacetate. The protonated alkoxide is then released as a molecule of alcohol and forms an oxonium cation which is then attached by the alcohol. Proton transfer steps then follow, protonating another alkoxide group, that is again lost as alcohol and forms another oxonium cation. A deprotonation step then produces a 1,5 diene intermediate which undergoes a Claisen sigmatropic rearrangement to provide the final γ,δ-unsaturated ester product.[1]
jones-oxidation	https://www.name-reaction.com/jones-oxidation	[ "alcohol", "carbonyl compound" ]	[ "acid catalyst", "alcohol" ]	[]	[]	acid	The Jones oxidation is an organic reaction used to oxidize alcohols using chromic trioxide and acid in water. A primary alcohol is oxidized to an aldehyde or all the way to a carboxylic acid, while a secondary alcohol to a ketone. The mechanism begins with the reaction of CrO3with acid (often H2SO4) to form chromic acid or dichromic acid in more concentrated solutions. The alcohol oxidation then occurs with chromic acid which in turn gets reduced in the process.[1]
knoevenagel-condensation	https://www.name-reaction.com/knoevenagel-condensation	[ "carbonyl compound" ]	[ "base catalyst" ]	[ "alkene" ]	[]	catalyst base	The Knoevenagel condensation is an organic reaction used to convert an aldehyde or ketone and an activated methylene to a substituted olefin using an amine base as a catalyst. The reaction begins by deprotonation of the activated methylene by the base to give a resonance stabilized enolate. The amine catalyst also reacts with the aldehyde or ketone to form an iminium ion intermediate, which then gets attacked by the enolate. The intermediate compound formed gets deprotonated by the base to give another enolate while the amine of the intermediate gets protonated. A rearrangement then ensues which releases the amine base, regenerates the catalyst, and yields the final olefin product.[1]
knorr-pyrazole-synthesis	https://www.name-reaction.com/knorr-pyrazole-synthesis	[ "carbonyl compound" ]	[ "base catalyst", "acid catalyst" ]	[ "ester" ]	[]	acid catalyst	The Knorr pyrazole synthesis is an organic reaction used to convert a hydrazine or its derivatives and a 1,3-dicarbonyl compound to a pyrazole using an acid catalyst. The mechanism begins with an acid catalyzed imine formation, where in the case of hydrazine derivatives the attack can happen on either carbonyl carbon and result in two possible products. The other nitrogen of the hydrazine derivative then attacks the other carbonyl group which has also been protonated by the acid and forms a second imine group. This diimine compound gets deprotonated to regenerate the acid catalyst and provide the final pyrazole product.[1]
kolbe-schmitt-reaction	https://www.name-reaction.com/kolbe-schmitt-reaction	[ "alcohol", "carbonyl compound" ]	[ "base catalyst", "acid catalyst" ]	[]	[]	acid base	The Kolbe-Schmitt reaction is an organic reaction used to convert a phenol to a hydroxy benzoic acid using carbon dioxide gas, a base, and acid work-up. The mechanism begins with deprotonation of the phenol by the base to form a phenoxide. The phenoxide rearranges to form a carbonyl group while the aromatic ring attacks the CO2molecule. The attack can happen from either the ortho or para position, which explains the two possible products, and results in the loss of aromaticity of the ring. Another deprotonation by the base regenerates aromaticity and produces the phenoxide again. Protonation of the phenoxide and the carboxy-late anions yield the final ortho- and/or para-hydroxy benzoic acids.[1][2]
kumada-cross-coupling	https://www.name-reaction.com/kumada-cross-coupling	[]	[ "base catalyst", "organometallic reagent" ]	[]	[]	catalyst	The Kumada cross-coupling reaction is the organic reaction of an organohalide with an organomagnesium compound, also known as a Grignard reagent, to give the coupled product using a palladium or nickel catalyst. The palladium catalyzed mechanism begins with oxidative addition of the organohalide to the Pd(0) to form a Pd(II) complex. Transmetalation with the Grignard reagent then follows, where the R group of the Grignard reagent replaces the halide anion on the palladium complex and makes a magnesium(II) halide salt. Reductive elimination then gives the final coupled product, regenerates the catalyst, and the catalytic cycle can begin again.[1]
luche-reduction	https://www.name-reaction.com/luche-reduction	[ "alcohol", "carbonyl compound" ]	[ "acid catalyst", "alcohol" ]	[]	[]	solvent	The Luche reduction is an organic reaction used to convert an α,β-unsaturated ketone to an allylic alcohol using cerium trichloride, sodium borohydride, and an alcohol solvent. The role of the cerium or other lanthanide metals is to coordinate to the alcohol, making its proton more acidic which allows for it to be abstracted by the carbonyl oxygen of the ketone starting material. The NaBH4starting regent also reacts with the cerium activated alcohol to form a series of alkoxyborohydrides and these "hard reagents" result in the 1,2 hydride attack on the protonated carbonyl to give the final allylic alcohol product.[1][2]
mannich-reaction	https://www.name-reaction.com/mannich-reaction	[ "carbonyl compound" ]	[ "base catalyst", "acid catalyst", "organometallic reagent" ]	[]	[]	acid catalyst base	The Mannich reaction is an organic reaction used to convert a primary or secondary amine and two carbonyl compound (one non-enolizable and one enolizable) to a β-amino carbonyl compound, also known as a Mannich base, using an acid or base catalyst. In the acid catalyzed mechanism both carbonyl compounds get protonated at the oxygen. The enolizable carbonyl compound, which has an α-hydrogen, then gets deprotonated to form an enol intermediate. The non-enolizable carbonyl compound reacts with the amine to form an iminium ion. The enol intermediate then attacks the iminium ion which after deprotonation provides the final Mannich base product.[1]
michael-addition	https://www.name-reaction.com/michael-addition	[ "carbonyl compound" ]	[ "base catalyst", "acid catalyst", "organometallic reagent" ]	[ "alkene" ]	[]	acid catalyst base	The Michael addition is an organic reaction used to convert an activated methylene and a conjugated olefin to the corresponding addition product using a base catalyst followed by an acid work-up. The activated methylene is essentially a methylene bonded to electron withdrawing groups that would stabilize the negative change that forms after deprotonation by the base. This deprotonation results in an enolate which in turn does a 1,4 addition to the conjugated olefin. An acid work-up then provides the final Michael addition product.[1]
mitsunobu-reaction	https://www.name-reaction.com/mitsunobu-reaction	[ "alcohol", "carbonyl compound" ]	[ "acid catalyst", "alcohol" ]	[ "ester" ]	[]	acid Acid	The Mitsunobu reaction is an organic reaction used to convert a primary or secondary alcohol into a variety of compounds using DEAD and triphenylphosphine. The final product depends on the acidic reagent (the conjugate acid of the nucleophile). The mechanism begins with attack of PPh3on DEAD which forms a zwitterionic intermediate. This intermediate then deprotonates the acidic compound to reveal the anionic nucleophile. The alcohol starting material then binds to the phosphonium ion and the nucleophile performs a SN2attack to yield the final substitution product with inversion of stereochemistry. The formation of a strong P=O in the by-product drives this reaction forward.[1][2]
mukaiyama-aldol-addition	https://www.name-reaction.com/mukaiyama-aldol-addition	[ "carbonyl compound" ]	[ "base catalyst", "acid catalyst", "organometallic reagent" ]	[]	[]	acid catalyst	The Mukaiyama aldol addition is an organic reaction used to convert an aldehyde and a silyl enol ether to a 1,3 ketol using a Lewis acid catalyst (such as TiCl4), followed by aqueous work-up. The mechanism begins by coordination of the aldehyde's oxygen to Titanium, which activate the carbonyl for attack while also releasing a chloride ion. The chloride attacks the silicon of the silyl enol ether to form TMSCl and an enolate. The enolate then attacks the activated carbonyl and subsequent aqueous work-up provides the final 1,3 ketol product.[1][2]
n	https://www.name-reaction.com/n	[ "carbonyl compound" ]	[ "acid catalyst", "organometallic reagent" ]	[ "ester" ]	[]	acid
negishi-cross-coupling	https://www.name-reaction.com/negishi-cross-coupling	[]	[ "base catalyst" ]	[]	[]	catalyst	The Negishi cross-coupling reaction is the organic reaction of an organohalide with an organozinc compound to give the coupled product using a palladium or nickel catalyst. The palladium catalyzed mechanism begins with oxidative addition of the organohalide to the Pd(0) to form a Pd(II) complex. Transmetalation with the organozinc then follows where the R group of the organozinc reagent replaces the halide anion on the palladium complex and makes a zinc(II) halide salt. Reductive elimination then gives the final coupled product, regenerates the catalyst, and the catalytic cycle can begin again.[1]
oppenauer-oxidation	https://www.name-reaction.com/oppenauer-oxidation	[ "alcohol", "carbonyl compound" ]	[ "base catalyst", "alcohol" ]	[]	[]	catalyst	The Oppenauer oxidation is an organic reaction used to convert a primary or secondary alcohol to a ketone using another excess ketone reagent (such as acetone) and an aluminium triisopropoxide catalyst. The mechanism begins with the alcohol replacing one of the isopropoxide groups on the aluminum to generate isopropanol. Acetone then coordinates to the aluminum complex and a rearrangement reaction occurs which includes a hydride transfer from the alcohol to acetone. This process, which oxidizes the alcohol and reduces the acetone, results in the formation of the final ketone product and regeneration of the aluminum triisopropoxide catalyst.[1]
pauson-khand-reaction	https://www.name-reaction.com/pauson-khand-reaction	[ "unsaturated compound" ]	[ "base catalyst", "organometallic reagent" ]	[ "alkene" ]	[]	catalyst	The Pauson-Khand reaction is an organic reaction used to convert an alkyne and alkene to a substituted cyclopentenone under an atmosphere of carbon monoxide and a dicobalt complex catalyst. This 2+2+1 cycloaddition reaction begins with the addition of the alkyne to the metal complex followed by ligand substitution of the alkene to expel a CO molecule. Alkene insertion follows and a subsequent CO insertion results in the formation of a carbonyl group. A series of reductive eliminations then yield the final cyclopentenone product and regenerates the cobalt catalyst.[1][2][3]
perkin-reaction	https://www.name-reaction.com/perkin-reaction	[ "carbonyl compound" ]	[ "base catalyst", "acid catalyst" ]	[]	[]	acid base	The Perkin reaction is an organic reaction used to convert an aromatic aldehyde and an anhydride to an α,β-unsaturated carboxylic acid using sodium acetate, a base, and an acid work-up. The regiochemistry of the reaction, the relative position of the carboxylic acid and aromatic ring in the final product, can be either E or Z. The mechanism goes through numerous steps including several additions and eliminations.[1]
pictet-spengler-reaction	https://www.name-reaction.com/pictet-spengler-reaction	[ "carbonyl compound" ]	[ "base catalyst", "acid catalyst" ]	[]	[]	acid catalyst	The Pictet-Spengler reaction is an organic reaction used to convert a β-arylenylamine and an aldehyde or ketone to a tetrahydroisoquinoline using an acid catalyst. The mechanism begins with protonation of the carbonyl oxygen by the acid which is subsequently attacked by the amine reagent. Proton transfer steps and the release of a water molecule results in a protonated imine intermediate, which then undergoes a 6-endo-trig cyclization reaction with loss of aromaticity of the aryl ring. A final deprotonation step restores the aromaticity and results in the tetrahydroisoquinoline product.[1]
prins-reaction	https://www.name-reaction.com/prins-reaction	[ "alcohol", "carbonyl compound", "unsaturated compound" ]	[ "organometallic reagent", "alcohol" ]	[ "alkene" ]	[]		The Prins reaction is an organic reaction used to convert an alkene and an aldehyde to a variety of products depending on the reaction conditions. All mechanisms begin with protonation of the aldehyde which is then attacked by the alkene to give a β-hydroxyl carbocation intermediate. Without the addition of other reagents this intermediate will react with water in an elimination reaction to give an allylic alcohol product. If nucleophiles are added to the reaction mixture they would directly attack the carbocation to give an alcohol, while if excess of the aldehyde reagent is used, the reaction will result in a 1,3-dioxane.[1][2]
reformatsky-reaction	https://www.name-reaction.com/reformatsky-reaction	[ "carbonyl compound" ]	[ "acid catalyst", "organometallic reagent" ]	[ "ester" ]	[]	acid	The Reformatsky reaction is an organic reaction used to convert an α-haloester and an aldehyde or ketone to a β-hydroxyester using zinc metal followed by an acid work-up. The reaction begins with oxidative addition of the zinc metal to the carbon-halogen bond of the α-haloester. Two of the resulting compounds coordinate to each other forming a dimer, which then undergoes a rearrangement to give two molecules of O-zinc enolates. The oxygen of the aldehyde or ketone reagent then coordinates to the zinc and another rearrangement ensues which joins the two reagents with a carbon-carbon bond. An acid work-up then cleaves the zinc-oxygen bond to give the final β-hydroxyester product and a zinc(II) salt.[1]
reimer-tiemann-reaction	https://www.name-reaction.com/reimer-tiemann-reaction	[ "alcohol", "carbonyl compound" ]	[ "base catalyst", "acid catalyst" ]	[]	[]	acid base	The Reimer-Tiemann reaction is an organic reaction used to convert a phenol to an o-hydroxy benzalde-hyde using chloroform, a base, and acid work-up. The mechanism begins with abstraction of the proton from chloroform with the base to form a trichlorocarbanion which spontaneously loses a chloride ion to form a neutral dichlorocarbene. The base also deprotonates the phenol reagent which then attacks the carbene. A series of steps and a final acid work-up result in the o-hydroxy benzaldehyde product.[1][2][3]
ritter-reaction	https://www.name-reaction.com/ritter-reaction	[ "alcohol", "carbonyl compound", "unsaturated compound" ]	[ "acid catalyst", "organometallic reagent", "alcohol" ]	[ "amide", "alkene" ]	[]	acid	The Ritter reaction is an organic reaction used to convert a nitrile and a carbocation precursor (such as a substituted olefin or tertiary alcohol) to an amide using a strong acid and water. The mechanism begins with the formation of the carbocation from the reaction of the acid with the carbocation precursor. The nitrile then attacks the carbocation to form a nitrilium ion. Water hydrolysis and a series of proton transfer steps then yield the final amide product.[1][2]
robinson-annulation	https://www.name-reaction.com/robinson-annulation	[ "carbonyl compound" ]	[ "base catalyst", "organometallic reagent" ]	[ "alkene" ]	[]	base	The Robinson annulation is an organic reaction used to convert a ketone and an α,β-unsaturated ketone to a cyclohexenone using base. The mechanism begins with deprotonation with the base of the α-hydrogen of the ketone to form an enolate. The enolate then does a 1,4 addition to the conjugated olefin (Michael addition), which then abstracks a proton from water to form a diketone. Deprotonation of the other α-hydrogen with base forms another enolate which then does in intramolecular attack on the ketone group to give a cyclic alkoxy intermediate. Protonation of the alkoxy and a final elimination step result in the cyclo-hexenone product.[1]
sandmeyer-reaction	https://www.name-reaction.com/sandmeyer-reaction	[]	[ "base catalyst" ]	[]	[]	catalyst	The Sandmeyer reaction is an organic reaction used to convert an aryl diazonium salt to an aryl halide using a copper(I) halide catalyst. The mechanism begins with a single electron transfer (SET) from the copper to the diazonium to form a neutral diaso radical and copper(II) halide. The diazo radical then releases a molecule of nitrogen gas to form an aryl radical. The aryl radical reacts with the copper(II) halide to regenerate the copper(I) halide catalyst and yield the final aryl halide product.[1][2]
schmidt-reaction	https://www.name-reaction.com/schmidt-reaction	[ "carbonyl compound" ]	[ "base catalyst", "acid catalyst" ]	[]	[]	acid catalyst	The Schmidt reaction is an organic reaction used to convert hydrazoic acid to a variety of products using an acid catalyst. The mechanism shown is for an aldehyde regent but it can be easily extended to the other regents. The reaction begins with abstraction of a proton from the acid by the aldehyde or other reagent to activate it for future attack. The generated water molecule then abstracts the proton from hydrazoic acid to regenerate the acid and produce an azide anion which then attacks the activated reagent. A series of steps and the release of a molecule of nitrogen gas result in the final product.[1][2]
schotten-baumann-reaction	https://www.name-reaction.com/schotten-baumann-reaction	[ "alcohol", "carbonyl compound" ]	[ "base catalyst", "alcohol" ]	[ "amide", "ester" ]	[]	base	The Schotten-Baumann reaction is an organic reaction used to convert an acyl halide or anhydride to an amide if reacted with an amine and base, or an ester if reacted with an alcohol and base. The reaction with the amine begins with the nitrogen attacking the carbonyl carbon of the acyl halide which rearranges to kick out the halide. Deprotonation with the base then provides the final amide product. The reaction with the alcohol would happen in a similar fashion.[1][2]
sharpless-epoxidation	https://www.name-reaction.com/sharpless-epoxidation	[ "alcohol" ]	[ "base catalyst", "alcohol" ]	[]	[]	catalyst	The Sharpless epoxidation is an organic reaction used to steroselectively convert an allylic alcohol to an epoxy alcohol using a titanium isopropoxide catalyst, t-butyl hydroperoxide (TBHP), and a chiral diethyl tartrate (DET). The mechanism begins with the displacement of the isopropoxide ligands on the titanium by DET, TBHP, and finally by the allylic alcohol reagent. This titanium complex is believed to exist as a dimer, but for simplicity is shown as a monomer in the mechanism. Oxidation of the olefin with TBHP then occurs where the chiral DET dictates the face of attack and leads to a steroselective epoxy alcohol.[1]
sonogashira-cross-coupling	https://www.name-reaction.com/sonogashira-cross-coupling	[ "unsaturated compound" ]	[ "base catalyst" ]	[ "alkene" ]	[]	catalyst base	The Sonogashira cross-coupling reaction is the organic reaction of an organohalide with a terminal alkyne to give the coupled product using a palladium catalyst, a copper catalyst, and base. The palladium cataly-zed mechanism begins with oxidative addition of the organohalide to the Pd(0) to form a Pd(II) complex. Transmetalation with the organocopper reagent, formed from the terminal alkyne and the copper catalyst, then follows. The alkynyl anion replaces the halide on the palladium complex and regenerates the copper halide catalyst. Reductive elimination then gives the final coupled product, regenerates the palladium catalyst, and the catalytic cycle can begin again.[1]
staudinger-reaction	https://www.name-reaction.com/staudinger-reaction	[ "triphenylphosphine", "as" ]	[ "is", "an" ]	[ "to", "pr" ]	[]		The Staudinger reaction is an organic reaction used to convert an organic azide to a primary amine using a PR3compound (such as triphenylphosphine) and water. The mechanism begins with attack of the phos-phorus on the far nitrogen of the organic azide to give a phosphazide intermediate. This intermediate then goes through a rearrangement that releases a molecule of nitrogen gas and forms a N-P ylide. The molecule of water then attacks the phosphorus atom and a series or proton transfer steps follow to result in the formation of the final primary amine and a triphenylphosphine oxide by-product.[1]
stille-cross-coupling	https://www.name-reaction.com/stille-cross-coupling	[ "carbonyl compound" ]	[ "base catalyst", "acid catalyst" ]	[]	[]	acid catalyst	The Stille cross-coupling reaction is the organic reaction of an organohalide with an organostannane com-pound to give the coupled product using a palladium catalyst. The mechanism begins with oxidative add-ition of the organohalide to the Pd(0) to form a Pd(II) complex. Transmetalation with the organostannane then follows where the R group of the organostannane reagent replaces the halide anion on the palladium complex. Reductive elimination then gives the final coupled product, regenerates the palladium catalyst, and the catalytic cycle can begin again.[1][2]
strecker-amino-acid-synthesis	https://www.name-reaction.com/strecker-amino-acid-synthesis	[ "carbonyl compound" ]	[ "base catalyst", "acid catalyst" ]	[ "amide" ]	[]	acid catalyst	The Strecker amino acid synthesis is an organic reaction used to convert an aldehyde or ketone and a pri-mary amine or ammonia to an α-amino acid using a metal cyanide, acid catalyst, and water. The mecha-nism begins with the acid catalyzed reaction of the carbonyl with the amine to give the corresponding imine. The imine is then attacked by the cyanide to provide a nitrile intermediate. The nitrile gets protonated by the acid, is attacked by a molecule of water and after a series of proton transfer steps results in an amide intermediate. In the reaction's acid conditions, the amide gets protonated and the amine group is displaced by water to eventually yield the carboxylic acid group and the final amino acid product.[1][2]
suzuki-cross-coupling	https://www.name-reaction.com/suzuki-cross-coupling	[]	[ "base catalyst" ]	[]	[]	catalyst base	The Suzuki cross-coupling reaction is the organic reaction of an organohalide with an organoborane to give the coupled product using a palladium catalyst and base. The mechanism begins with oxidative addition of the organohalide to the Pd(0) to form a Pd(II) complex. A molecule of the hydroxide or alkoxide base then replaces the halide on the palladium complex, while another adds to the organoborane to form a borate regent making its R group more nucleophilic. Transmetalation with the borate then follows where its R group replaces the halide anion on the palladium complex. Reductive elimination then gives the final coupled product, regenerates the palladium catalyst, and the catalytic cycle can begin again.[1][2]
swern-oxidation	https://www.name-reaction.com/swern-oxidation	[ "alcohol", "carbonyl compound" ]	[ "alcohol" ]	[]	[]		The Swern oxidation is an organic reaction used to convert a primary alcohol to an aldehyde and a secon-dary alcohol to a ketone using DMSO, oxalyl chloride, and triethylamine. The mechanism begins with the activation of DSMO with oxalyl chloride which is then attacked by a chloride anion to form a chlorosulfo-nium cation and release both CO and CO2gas. The alcohol then attacks the chlorosulfonium salt which releases the chloride anion and forms an alkoxysulfonium cation. Triethylamine then deprotonates the alkoxysulfonium at the alpha position to form a alkoxysulfonium ylide. A rearrangemnt then ensues which releases a molecule of dimethyl sulfide gas and results in the final aldehyde or ketone product.[1][2]
ullmann-reaction	https://www.name-reaction.com/ullmann-reaction	[ "halide", "alkyl halide" ]	[ "as", "or" ]	[ "is", "an" ]	[]		The Ullmann reaction is an organic reaction used to couple two molecules of aryl halide to form a biaryl using copper metal and thermal conditions. The mechanism for the Ullmann reaction is not fully under-stood but there are two popular mechanisms. The radical mechanism begins with a single electron transfer (SET) from the copper metal to the alkyl halide to form an aryl radical. Two aryl radical then react to form the final biaryl product. The second proposed mechanism begins with oxidative addition of the copper to the aryl halide followed by a SET to form an organocuprate reagent. The organocuprate performs another oxidative addition on an aryl halide and after reductive elimination results in the final biaryl product.[1][2]
vilsmeier-haack-reaction	https://www.name-reaction.com/vilsmeier-haack-reaction	[ "carbonyl compound" ]	[ "acid catalyst" ]	[]	[]	acid	The Vilsmeier-Haack reaction is an organic reaction used to convert an electron rich aromatic ring to an aryl aldehyde using DMF, an acid chloride, and aqueous work-up. The mechanism begins with the reaction of DMF with the acid chloride to form an iminium salt known as the "Vilsmeier reagent". The electron rich aromatic ring then attacks the iminium ion with loss of aromaticity. A deprotonation step restores aromati-city, which is followed by the release of a chloride ion to form another iminium intermediate. Aqueous work-up then leads to the aryl aldehyde final product.[1]
wagner-meerwein-rearrangement	https://www.name-reaction.com/wagner-meerwein-rearrangement	[ "alcohol", "carbonyl compound" ]	[ "base catalyst", "acid catalyst", "alcohol" ]	[ "alkene" ]	[]	acid catalyst	The Wagner-Meerwein rearrangement is an organic reaction used to convert an alcohol to an olefin using an acid catalyst. The mechanism begins with protonation of the alcohol by the acid which is then released as water to forms a carbocation. A 1,2-shift then occurs to form a more substituted and stabilized carbo-cation. A final deprotonation with water produces the final olefin product and regenerates the acid catalyst.[1][2]
williamson-ether-synthesis	https://www.name-reaction.com/williamson-ether-synthesis	[ "alcohol" ]	[ "base catalyst", "alcohol" ]	[]	[]	base	The Williamson ether synthesis is an organic reaction used to convert an alcohol and an alkyl halide to an ether using a base such as NaOH. The mechanism begins with the base abstracting the proton from the alcohol to form an alkoxide intermediate. The alkoxide then attacks the alkyl halide in a nucleophilic substi-tution reaction (SN2), which results in the formation of the final ether product and a metal halide by-product.[1][2]
wittig-reaction	https://www.name-reaction.com/wittig-reaction	[ "carbonyl compound", "aldehyde", "ketone" ]	[ "phosphorus ylide", "wittig reagent" ]	[]	[ "triphenylphosphine oxide", "Ph3P=O" ]	base	The Wittig reaction is an organic reaction used to convert a primary or secondary alkyl halide and an aldehyde or ketone to an olefin using triphenylphosphine and base. The mechanism beings with attack of the PPH3on the alkyl halide which releases the halide anion and forms a phosphonium ion. The base then deprotonates at the alpha position to afford a phosphonium ylide. The ylide subsequently attacks the alde-hyde or ketone to form a zwitterion where the oxygen anion then attacks the phosphonium cation to form an oxaphosphetane. A rearrangement then generates the final olefin product and releases a triphenylphos-phine oxide by-product whose formation of a strong P=O bond is the driving force for this reaction.[1][2]
wolff-rearrangement	https://www.name-reaction.com/wolff-rearrangement	[ "carbonyl compound" ]	[ "base catalyst" ]	[]	[]	catalyst	The Wolff rearrangement is an organic reaction used to convert an α-diazo ketone to a ketene using a silver oxide catalyst, light, or thermal conditions. The mechanism of the Wolff rearrangement is essentially one step which is initiated by the catalyst. The reaction involves a 1,2-shift to form the ketene product and release a molecule of nitrogen gas. Subsequent attacks by nucleophiles to the ketene formed are also considered Wolff rearrangement.[1]
wolff-kishner-reduction	https://www.name-reaction.com/wolff-kishner-reduction	[ "carbonyl compound" ]	[ "base catalyst" ]	[]	[]	catalyst base	The Wolff-Kishner reduction is an organic reaction used to convert an aldehyde or ketone to an alkane using hydrazine, base, and thermal conditions. The mechanism begins with the attack of hydrazine of the aldehyde or ketone for form an imine. Proton transfer steps then result in the formation of a N=N bond. Deprotonation of the nitrogen and a rearrangement reaction result in the formation of a carbanion and the release of nitrogen gas. The carbanion then picks up a proton from water to regenerate the base catalyst and provides the final alkane product.[1][2]
wurtz-reaction	https://www.name-reaction.com/wurtz-reaction	[ "alkyl halide", "halide" ]	[ "as", "is" ]	[ "an", "to" ]	[]		The Wurtz reaction is an organic reaction used to couple two alkyl halides to form an alkane using sodium metal. The mechanism begins with a single electron transfer (SET) from sodium metal to the alkyl halide, which dissociates to form an alkyl radical and sodium halide salt. Another molecule of sodium performs another SET to the alkyl radical to form a nucleophilic carbanion. The carbanion then attacks another molecule of alkyl halide in a nucleophilic substitution reaction (SN2) to form the final coupled product and another molecule of sodium halide salt.[1][2]
yamaguchi-esterification	https://www.name-reaction.com/yamaguchi-esterification	[ "alcohol", "carbonyl compound" ]	[ "acid catalyst", "alcohol" ]	[ "ester" ]	[]	acid	The Yamaguchi esterification is an organic reaction used to convert a carboxylic acid and an alcohol to an ester using triethylamine, the Yamaguchi reagent, and DMAP. The mechanism begins with deprotonation of the carboxylic acid by Et3N to form a carboxylate anion which then attacks the Yamaguchi reagent. The resultant acid anhydride get attacked by DMAP to form a better leaving group which is then displaced by the alcohol reagent. A final deprotonation step results in the ester product.[1]
0-9[edit]	https://en.wikipedia.org/w/index.php?title=List_of_organic_reactions&action=edit&section=1	[ "to", "us" ]	[ "log", "in" ]	[]	[]
1,2-Wittig rearrangement	https://en.wikipedia.org/wiki/1,2-Wittig_rearrangement	[ "to", "us" ]	[ "log", "in" ]	[]	[]
1,3-Dipolar cycloaddition	https://en.wikipedia.org/wiki/1,3-Dipolar_cycloaddition	[ "to", "us" ]	[ "log", "in" ]	[]	[]
2,3-Wittig rearrangement	https://en.wikipedia.org/wiki/2,3-Wittig_rearrangement	[ "to", "us" ]	[ "log", "in" ]	[]	[]
A[edit]	https://en.wikipedia.org/w/index.php?title=List_of_organic_reactions&action=edit&section=2	[ "to", "us" ]	[ "log", "in" ]	[]	[]
Abramovitch�Shapiro tryptamine synthesis	https://en.wikipedia.org/wiki/Tryptamine	[ "to", "us" ]	[ "log", "in" ]	[]	[]
Acetalisation	https://en.wikipedia.org/wiki/Acetalisation	[ "to", "us" ]	[ "log", "in" ]	[]	[]
Acetoacetic ester condensation	https://en.wikipedia.org/wiki/Acetoacetic_ester_condensation	[ "to", "us" ]	[ "log", "in" ]	[]	[]
Achmatowicz reaction	https://en.wikipedia.org/wiki/Achmatowicz_reaction	[ "to", "us" ]	[ "log", "in" ]	[]	[]
Acylation	https://en.wikipedia.org/wiki/Acylation	[ "to", "us" ]	[ "log", "in" ]	[]	[]
Acyloin condensation	https://en.wikipedia.org/wiki/Acyloin_condensation	[ "to", "us" ]	[ "log", "in" ]	[]	[]
Adams' catalyst	https://en.wikipedia.org/wiki/Adams%27_catalyst	[ "to", "us" ]	[ "log", "in" ]	[]	[]
Adams decarboxylation	https://en.wikipedia.org/wiki/Adams_decarboxylation	[ "to", "us" ]	[ "log", "in" ]	[]	[]
Adkins catalyst	https://en.wikipedia.org/wiki/Adkins_catalyst	[ "to", "us" ]	[ "log", "in" ]	[]	[]
Adkins�Peterson reaction	https://en.wikipedia.org/wiki/Adkins%E2%80%93Peterson_reaction	[ "to", "us" ]	[ "log", "in" ]	[]	[]
Akabori amino acid reaction	https://en.wikipedia.org/wiki/Akabori_amino_acid_reaction	[ "to", "us" ]	[ "log", "in" ]	[]	[]
Alcohol oxidation	https://en.wikipedia.org/wiki/Alcohol_oxidation	[ "to", "us" ]	[ "log", "in" ]	[]	[]
Alder�Stein rules	https://en.wikipedia.org/wiki/Alder%E2%80%93Stein_rules	[ "to", "us" ]	[ "log", "in" ]	[]	[]
Aldol addition	https://en.wikipedia.org/wiki/Aldol_addition	[ "to", "us" ]	[ "log", "in" ]	[]	[]
Aldol condensation	https://en.wikipedia.org/wiki/Aldol_condensation	[ "to", "us" ]	[ "log", "in" ]	[]	[]
Algar�Flynn�Oyamada reaction	https://en.wikipedia.org/wiki/Algar%E2%80%93Flynn%E2%80%93Oyamada_reaction	[ "to", "us" ]	[ "log", "in" ]	[]	[]
Alkylimino-de-oxo-bisubstitution	https://en.wikipedia.org/wiki/Alkylimino-de-oxo-bisubstitution	[ "to", "us" ]	[ "log", "in" ]	[]	[]
Alkyne trimerisation	https://en.wikipedia.org/wiki/Alkyne_trimerisation	[ "to", "us" ]	[ "log", "in" ]	[]	[]
Alkyne zipper reaction	https://en.wikipedia.org/wiki/Alkyne_zipper_reaction	[ "to", "us" ]	[ "log", "in" ]	[]	[]
Allan�Robinson reaction	https://en.wikipedia.org/wiki/Allan%E2%80%93Robinson_reaction	[ "to", "us" ]	[ "log", "in" ]	[]	[]

appel-reaction

https://www.name-reaction.com/appel-reaction

[ "alcohol", "ROH" ]

[ "triphenylphosphine", "PPh3", "tetrahalomethane" ]

[ "alkyl halide", "RCl" ]

[ "triphenylphosphine oxide", "Ph3P=O" ]

The Appel reaction is an organic reaction used to convert an alcohol to an alkyl halide using a tetrahalomethane and triphenylphosphine. The reaction begins with the halogenation of triphenyl-phosphine followed by the formation of the alkoxide from the alcohol starting material. The alkoxide subsequently attacks the phosphorous, releasing the halide leaving group. In a nucleophilic substitution reaction (SN2), the halide (nucleophile) attacks the carbon stereocenter resulting in the the final alkyl halide product with inverted stereochemistry. Triphenylphosphine oxide is a byproduct of this reaction and the formation of the strong P=O double bond is a driving force for this reaction.[1]

baeyer-villiger-oxidation

https://www.name-reaction.com/baeyer-villiger-oxidation

[ "carbonyl compound" ]

[ "acid catalyst" ]

[ "ester" ]

[]

acid

The Baeyer-Villiger oxidation is an organic reaction used to convert a ketone to an ester using a peroxyacid (such as mCPBA). The reaction of the ketone with the acid results in a tetrahedral intermediate, with an alkyl migration following to release a carboxylic acid. The more electron rich R group migrates to the oxygen in this concerted process, allowing for accurate prediction of the stereochemistry of the product.[1]

bartoli-indole-synthesis

https://www.name-reaction.com/bartoli-indole-synthesis

[ "carbonyl compound" ]

[ "acid catalyst", "organometallic reagent" ]

[]

acid

The Bartoli indole synthesis is an organic reaction where a substituted nitroarene is converted to an indole using an excess of a vinyl Grignard reagent followed by an acid work-up. The substituents on the nitroarene affect the yield of this reaction where the highest yields are observed for ortho substituted reagents and the bulkier groups usually result in higher yields. The Bartoli indole synthesis mechanism begins with a series of attacks on the nitroarene regent by the Grigrand reagents and is then followed by a 3,3 sigmatropic rearrangement (Claisen) step which results in an aldehyde intermediate. The aldehyde is then quickly attacked by the nearby nitrogen intramolecularly and a subsequent attack by the third equivalent of the Grignard reagent restored aromaticity. A final acid work-up step affords the indole product.[1][2]

baylis-hillman-reaction

https://www.name-reaction.com/baylis-hillman-reaction

[ "carbonyl compound" ]

[ "base catalyst", "organometallic reagent" ]

[]

catalyst

The Baylis-Hillman reaction is an organic reaction used to form a C-C bond between an α-β unsaturated carbonyl compound and an aldehyde, activated ketone, or other carbon electrophiles. This reaction is most commonly catalyzed by DABCO but other tertiary amines or phosphines can also be used as catalysts. The catalyst activates the conjugated carbonyl compound to form a stabilized nucleophilic anion which subsequently attacks the electrophile. The reaction proceeds to afford the final product and regenerate the catalyst.[1]

beckmann-rearrangement

https://www.name-reaction.com/beckmann-rearrangement

[ "alcohol", "carbonyl compound" ]

[ "acid catalyst", "alcohol" ]

[ "amide" ]

[]

The Beckmann rearrangement is an organic reaction used to convert an oxime to an amide under acidic conditions. The reaction begins by protonation of the alcohol group forming a better leaving group. The R grouptransto the leaving group then migrates to the nitrogen, resulting in a carbocation and the release of a water molecule. Thistrans[1-2]-shift allows for the prediction of the regiochemistry of this reaction. The water molecule then attacks the carbocation and after deprotonation and tautomerization results in the final amide product.[1]

biginelli-reaction

https://www.name-reaction.com/biginelli-reaction

[ "alcohol", "carbonyl compound" ]

[ "acid catalyst", "alcohol" ]

[ "amide", "ester" ]

[]

acid

The Biginelli reaction is a one-pot three-component organic reaction between a β-keto ester, an aryl aldehyde, and urea to produce pyrimidones under acidic conditions. This reaction begins with protonation of the aldehyde by the acid and is followed by attack of the amine from urea. Proton transfer steps then result in a protonated alcohol which leaves as water to form an N-acyliminium ion intermediate. The intermediated is then attacked by the enol form of the β-keto ester. Reaction of the other amine group to the carbonyl produces a cyclic intermediate. Proton transfer steps, the release of water, and deprotonation result in the final pyrimidone product.[1][2]

birch-reduction

https://www.name-reaction.com/birch-reduction

[ "alcohol" ]

[]

The Birch reduction is an organic reaction where aromatic rings undergo a 1,4-reduction to provide unconjugated cyclohexadienes. The reduction is conducted by sodium or lithium metal in liquid ammonia and in the presence of an alcohol. The mechanism begins with a single electron transfer(SET) from the metal to the aromatic ring, forming a radical anion. The anion then picks up a proton from the alcohol which results in a neutral radical intermediate. Another SET, and abstraction of a proton from the alcohol results in the final cyclohexadiene product and two equivalents of metal alkoxide salt as a byproduct. In the case of substituted aromatic rings, the regiochemistry can be predicted using Birch's empirical rules.[1]

buchwald-hartwig-amination

https://www.name-reaction.com/buchwald-hartwig-amination

[]

[ "base catalyst" ]

[ "amide" ]

[]

catalyst base

The Buchwald-Hartwig amination is an organic reaction used to make carbon-nitrogen bonds. This is essentially a cross-coupling reaction of an aryl halide with an amine using palladium as a catalyst and a strong base. The reaction begins by oxidative addition of the aryl halide to the palladium which is followed by coordination of the amine to the palladium. The strong base then abstracts a proton from the amine, forming an amide, which in turn attacks the palladium and kicks out the halide as a leaving group. Reductive elimination then produces the final aryl amine product and regenerates the catalyst.[1][2]

cannizzaro-reaction

https://www.name-reaction.com/cannizzaro-reaction

[ "alcohol", "carbonyl compound" ]

[ "base catalyst", "acid catalyst", "alcohol" ]

[ "ester" ]

[]

acid base

The Cannizzaro reaction is a redox reaction in which two molecules of an aldehyde are reacted to produce a primary alcohol and a carboxylic acid using a hydroxide base. The reaction begins with hydroxide attack on the carbonyl carbon followed by deprotonation to give a dianion. This unstable intermediate releases a hydride anion which attacks another molecule of aldehyde. In this process the dianion converts to a carboxylate anion and the aldehyde to an alkoxide. The alkoxide then picks up a proton from water to provide the alcohol final product, while the caboxylate is converted to the carboxylic acid product after acid work-up.[1]

claisen-condensation

https://www.name-reaction.com/claisen-condensation

[ "alcohol", "carbonyl compound" ]

[ "base catalyst", "alcohol" ]

[ "ester" ]

[]

solvent base

The Claisen condensation is an organic reaction used to form a carbon-carbon bond between two ester molecules using an alkoxide base in alcohol to make a β-keto ester. The R group of the ester starting material, the alkoxide base, and the alcohol solvent are chosen to be the same to not end up with a mixture of products. The ester starting material must have an α-hydrogen which is abstracted by the base to form an enolate and alcohol. The enolate then attacks the carbonyl carbon of another ester molecule, an OR group is released to regenerate the base, and the final β-keto ester product is formed. The intramolecular form of the Claisen condensation is theDieckmann condensation.[1]

claisen-rearrangement

https://www.name-reaction.com/claisen-rearrangement

[ "alcohol", "carbonyl compound" ]

[ "acid catalyst" ]

[]

acid heat

The Claisen rearrangement is an organic reaction where an allyl vinyl ether is converted into a γ,δ-unsaturated carbonyl compound with the input of heat or a Lewis acid. This reaction belongs to a class of reactions termed "sigmatropic rearrangements" and it is a concerted process where bonds are forming and breaking at the same time. When substituents are present in the allyl vinyl ether starting material, the stereochemistry of this reaction can be predicted by drawing the molecule in a chair-like conformation and placing the substituents in the equatorial position to minimize the steric interactions.[1][2]

clemmensen-reduction

https://www.name-reaction.com/clemmensen-reduction

[ "carbonyl compound" ]

[ "acid catalyst" ]

[]

acid

The Clemmensen reduction is an organic reaction used to reduce an aldehyde or ketone to an alkane using amalgamated zinc and hydrochloric acid. The mechanism for the Clemmensen reduction is not yet fully understood and there are two popular proposals. The "Carbanionic mechanism", where the zinc attacks the protonated carbonyl directly, and the "Carbenoid mechanism", which is a radical process and the reduction happens on the surface of the zinc metal.[1][2][3]

cope-rearrangement

https://www.name-reaction.com/cope-rearrangement

[ "is", "an" ]

[ "to", "of" ]

[ "it", "at" ]

[]

The Cope rearrangement is an organic reaction where a 1,5-diene, under thermal conditions, is converted to another 1,5-diene structural isomer. This reaction belongs to a class of reactions termed "sigma tropic rearrangements" and it is a concerted process where bonds are forming and breaking at the same time. When substituents are present in the initial diene starting material, the stereochemistry of this reaction can be predicted by drawing the molecule in a chair-like conformation. Placing the substituents in the equatorial position minimizes the steric interactions and leads to the major product. The Cope rearrangement is an equilibrium reaction and the equilibrium position is determined by the overall stability of the starting material and product.[1]

corey-kim-oxidation

https://www.name-reaction.com/corey-kim-oxidation

[ "alcohol", "carbonyl compound" ]

[ "alcohol" ]

[]

The Corey-Kim oxidation is an organic reaction used to convert an alcohol to an aldehyde or ketone using N-chlorosuccinimide (NCS), dimethylsulfide (DMS) and triethylamine (TEA). The mechanism begins with the reaction of DMS with NCS to afford S,S-dimethylsuccinimidosulfonium chloride, also known as "Corey-Kim reagent". This electrophilic reagent is then attacked by the nucleophilic oxygen of the alcohol to form a S-O bond. The addition of TEA results in deprotonation of one of the methyl groups to form a zwitterionic species that undergoes a rearrangement reaction to release DMS gas and provide the final product.[1]

curtius-rearrangement

https://www.name-reaction.com/curtius-rearrangement

[ "as", "is" ]

[ "an", "to" ]

[ "of", "gas" ]

[]

The Curtius rearrangement is an organic reaction used to convert an acyl azide to an isocyanate under thermal conditions. The mechanism consists of an alkyl shift of the R group from the carbonyl carbon to the closest nitrogen with the release of nitrogen gas. The release of gas drives the reaction forward and results in the formation of the isocyanate product which can potentially react further in the presence of nucleophiles in solution.[1][2][3]

dakin-west-reaction

https://www.name-reaction.com/dakin-west-reaction

[ "carbonyl compound" ]

[ "base catalyst", "acid catalyst" ]

[]

acid base

The Dakin-West reaction is an organic reaction used to convert an amino acid and an anhydride to an acylamino ketone using a base and thermal conditions. The reaction begins with acylation of the amino acid on both terminals, first on the amine group, and then on the carboxylic acid group. An intramolecular reaction then follows to give a lactone intermediate. A series of addition and elimination steps and the release of carbon dioxide gas provide the acylamino ketone product.[1][2][3]

dieckmann-condensation

https://www.name-reaction.com/dieckmann-condensation

[ "alcohol", "carbonyl compound" ]

[ "base catalyst", "acid catalyst", "alcohol" ]

[ "ester" ]

[]

acid base

The Dieckmann condensation is an organic reaction used to form a carbon-carbon bond between two tethered ester groups using an alkoxide base in alcohol to make a cyclic β-keto ester. This reaction is essentially an intramolecular form of theClaisen condensation. One ester group of the starting material must have an α-hydrogen which is abstracted by the base to form an enolate and alcohol. The enolate then attacks the carbonyl carbon of another ester molecule, an OR group is released to regenerate the base, and the final β-keto ester product is formed. The product in base is then deprotonated again to form another enolate intermediate and acid-workup is required to isolate the final cyclic β-keto ester product.[1]

diels-alder-reaction

https://www.name-reaction.com/diels-alder-reaction

[]

[ "alkene" ]

[]

The Diels-Alder reaction is an organic reaction used to convert a conjugated diene and a dienophile to a cyclic olefin under thermal conditions. This is a concerted process where bonds are forming and breaking at the same time and the reaction belongs to a class of reactions termed "cycloaddition". The Diels-Alder reaction is by far the most famous 'name reaction' and it is extensively used in natural product synthesis. When predicting the regiochemistry and stereochemistry of the product, things to consider are the electronic character of the substitutes on the diene and dienophile, the partial charges formed, and the orientation of the starting materials when they approach each other.[1][2][3]

eschenmoser-claisen-rearrangement

https://www.name-reaction.com/eschenmoser-claisen-rearrangement

[ "alcohol" ]

[ "amide" ]

[]

The Eschenmoser-Claisen rearrangement is an organic reaction where an allylic alcohol is heated with N,N-dimethylacetamide dimethyl acetal to produce a γ,δ-unsaturated amide. The reactions begins with the release of a methoxide group from the amide starting material to produce an iminium cation which is then attacked by the alcohol. Proton transfer steps then follow which place the proton on the remaining methoxide group which is then released as a molecule of methanol and another iminium cation is formed. Deprotonation with methoxide produces a 1,5 diene intermediate which undergoes a Claisen sigmatropic rearrangement to provide the final γ,δ-unsaturated amide product.[1]

eschweiler-clarke-reaction

https://www.name-reaction.com/eschweiler-clarke-reaction

[ "carbonyl compound" ]

[ "acid catalyst" ]

[]

acid

The Eschweiler-Clarke reaction is an organic reaction used to convert a primary or secondary amine to a tertiary amine using formaldehyde and formic acid. This is essentially an amine methylation process which begins with the reaction of the amine starting material with the protonated formaldehyde to provide an intermediate iminium ion. The iminium ion then reacts with the formic acid to give a methylated ammonium ion and release carbon dioxide gas which drives the process forward. Deprotonation of the ammonium ion affords the final methylated amine product. In the case of primary amine starting materials, these steps repeat twice to give the tertiary amine final product.[1][2]

finkelstein-reaction

https://www.name-reaction.com/finkelstein-reaction

[ "alkyl halide", "halide" ]

[ "is", "an" ]

[ "by", "it" ]

[]

The Finkelstein reaction is an organic reaction where an alkyl halide is converted into another alkyl halide by reacting with a metal halide salt. This is an equilibrium process and it is driven forward by taking advantage of the poor solubility in acetone of the newly formed metal halide salt (Le Chatelier's principle). The mechanism for this reaction is a simple, single-step bimolecular nucleophilic substitution reaction (SN2) which like all SN2 reactions occur with inversion of stereochemistry.[1]

fischer-esterification

https://www.name-reaction.com/fischer-esterification

[ "alcohol", "carbonyl compound" ]

[ "base catalyst", "acid catalyst", "alcohol" ]

[ "ester" ]

[]

acid catalyst

The Fischer esterification is an organic reaction used to convert a carboxylic acid and an alcohol to an ester using an acid catalyst. The mechanism begins with protonation of the carbonyl group of the carboxylic acid, which is then attacked by the alcohol. Proton transfer and the subsequent release of water result in an oxonium ion intermediate. A final deprotonation step provides the ester product.[1]

fischer-indole-synthesis

https://www.name-reaction.com/fischer-indole-synthesis

[ "carbonyl compound" ]

[ "base catalyst", "acid catalyst" ]

[]

acid catalyst

The Fischer indole synthesis is an organic reaction used to convert a phenyl hydrazine and an aldehyde or ketone to an indole using an acid catalyst. The mechanism begins with formation of a phenylhydrazone through the acid catalyzed reaction of the hydrazine with the carbonyl. The phenylhydrazone then rearranges to the enamine and gets protonated on the phenyl nitrogen. An "ene reaction" (3,3-sigmatropic rearrangement) ensues, resulting in a diimine and loss of aromaticity. Additional key steps include rearomatization, formation of a cyclic aminal, and the expulsion of ammonia to give the indole product.[1][2]

friedel-crafts-acylation

https://www.name-reaction.com/friedel-crafts-acylation

[ "carbonyl compound" ]

[ "base catalyst", "acid catalyst" ]

[ "ester" ]

[]

acid catalyst

The Friedel-Crafts acylation is an organic reaction used to convert an aryl compound and an acyl halide or anhydride to an aryl ketone using a Lewis acid catalyst (such as AlCl3). The reaction begins with the Lewis acid abstracting the halide (or carboxylate) from the acyl halide (or ester) to form an electrophilic acylium cation and a tetrasubstituted aluminum anion. The aromatic compound then attacks the acylium ion via an electrophilic aromatic substitution (SEAr) to give a cationic product with loss of aromaticity. Deprotonation with the aluminum anion results in the final aryl ketone and regeneration of the Lewis acid catalyst.[1]

friedel-crafts-alkylation

https://www.name-reaction.com/friedel-crafts-alkylation

[ "carbonyl compound" ]

[ "base catalyst", "acid catalyst" ]

[]

acid catalyst

The Friedel-Crafts alkylation is an organic reaction used to convert an aryl compound and an alkyl halide to a substituted aromatic compound using a Lewis acid catalyst (such as AlCl3). The reaction begins with the Lewis acid abstracting the halide from the alkyl halide to form an electrophilic alkyl cation and a tetrasubstituted aluminum anion. The aromatic compound then attacks the alkyl cation via an electrophilic aromatic substitution (SEAr) to give a cationic product with loss of aromaticity. Deprotonation with the aluminum anion results in the final aromatic product and regeneration of the Lewis acid catalyst.[1]

fries-rearrangement

https://www.name-reaction.com/fries-rearrangement

[ "carbonyl compound" ]

[ "base catalyst", "acid catalyst" ]

[ "ester" ]

[]

acid catalyst

The Fries rearrangement is an organic reaction used to convert a phenyl ester to an ortho- and para-hydroxy aryl ketone using a Lewis acid catalyst and Brønsted acid work-up. The mechanism begins with coordination of the ester to the Lewis acid, followed by a rearrangement which generates an electrophilic acylium cation. The aromatic compound then attacks the alkyl cation (both the ortho and para attack are allowed) via an electrophilic aromatic substitution (SEAr). Deprotonation to regenerate aromaticity and Brønsted acid work-up to regenerate the Lewis acid catalyst provide the two hydroxy aryl ketone products.[1][2]

gabriel-synthesis

https://www.name-reaction.com/gabriel-synthesis

[ "carbonyl compound" ]

[ "base catalyst", "acid catalyst" ]

[]

acid base

The Gabriel synthesis is an organic reaction used to convert an alkyl halide to a primary amine using phthalimide with base and followed by hydrazine. The reaction begins with the deprotonation of the phthalimide which then attacks the alkyl halide in an SN2 fashion to give an N-alkylphthalimide intermediate. The intermediate is then cleaved by hydrazine in a series of steps that end with the liberation of the final primary amine product and phthalhydrazide by-product.[1]

grignard-reaction

https://www.name-reaction.com/grignard-reaction

[ "alkyl halide", "R-X" ]

[ "magnesium", "Mg" ]

[ "grignard reagent", "RMgX" ]

[]

acid

The Grignard reaction is an organic reaction used to create a variety of products through the reaction of an organomagnesium compound, also known as a "Grignard reagent" with an electrophile, followed by acid work-up. The Grignard reagent is formed through the reaction of an alkyl or aryl halide with magnesium metal via a radical mechanism. The mechanism of the subsequent reaction of the Grignard reagent with the electrophile is debatable. The most popular proposals are a "concerted mechanism" or another "radical mechanism", both can explain the final addition product.[1][2]

heck-reaction

https://www.name-reaction.com/heck-reaction

[ "unsaturated compound" ]

[ "base catalyst" ]

[ "alkene" ]

[]

Base catalyst base

The Heck reaction is a cross-coupling reaction of an organohalide with an alkene to make a substituted alkene using palladium as a catalyst and a base. The reaction begins by oxidative addition of the aryl halide to the palladium, which is followed by coordination and migratory insertion of the olefin to the palladium. Bond rotation then places the two groups trans to each other to relieve the steric strain and subsequent β-hydride elimination results in a trans final product. Base mediated reductive elimination regenerates the palladium(0) catalyst.[1][2][3]

hell-volhard-zelinsky-reaction

https://www.name-reaction.com/hell-volhard-zelinsky-reaction

[ "carbonyl compound" ]

[ "base catalyst", "acid catalyst" ]

[ "ester" ]

[]

acid catalyst

The Hell-Volhard-Zelinsky reaction is an organic reaction used to convert a carboxylic acid with an α-hydrogen and a halogen, to an α-halo carboxylic acid, using a phosphorous catalyst and water. The mechanism begins with the reaction of the carbonyl oxygen with phosphorous trihalide to form a P–O bond and release a halide anion. The halide then attacks the carbonyl to form an intermediate which rearranges to release an acyl chloride, an acid molecule, and a phosphine oxide. The acyl chloride then tautomerizes to the enol form which subsequently attacks the halogen molecule to form an α-halo acyl halide. Water hydrolysis yields the final α-halo carboxylic acid product.[1][2][3]

henry-reaction

https://www.name-reaction.com/henry-reaction

[ "alcohol", "carbonyl compound" ]

[ "base catalyst", "acid catalyst", "organometallic reagent" ]

[]

acid catalyst base

The Henry reaction is an organic reaction used to convert a nitroalkane with an α-hydrogen and an aldehyde or ketone to a β-nitro alcohol using a base catalyst. The mechanism begins with deprotonation of the nitroalkane by the base to give a resonance stabilize anionic intermediate which subsequently attacks the carbonyl compound to form an alkoxide. The alkoxide then picks up a proton from the conjugate acid of the base (H2O in this case) to give the final β-nitro alcohol product and regenerate the base catalyst.[1]

hofmann-elimination

https://www.name-reaction.com/hofmann-elimination

[ "unsaturated compound" ]

[ "base catalyst" ]

[ "alkene" ]

[]

The Hofmann elimination is an organic reaction used to convert an amine with a β-hydrogen to an alkene using methyl iodide, silver oxide and water under thermal conditions. The mechanism begins with an attack of the amine on methyl iodide to form an ammonium iodide salt. The iodide then reacts with silver oxide to form silver iodide which is insoluble and precipitates out of solution and a silver oxide ion which deproto-nates water to form a hydroxide ion. Heating the mixture facilitates an elimination reaction where the hydroxide picks up the β-hydrogen from the ammonium ion and releases an amine to afford the final olefin product.[1][2]

hofmann-rearrangement

https://www.name-reaction.com/hofmann-rearrangement

[]

[ "base catalyst" ]

[ "amide", "ester" ]

[]

heat base

The Hofmann rearrangement is an organic reaction used to convert a primary amide to a primary amine using a halogen, base, water, and heat. The reaction begins with deprotonation of the amide by the base to form an anion which then attacks the halogen to form a N-haloamide. A second deprotonation by the base provides an anion that rearranges to an isocyanate intermediate and releases a halide anion. The isocyanate is then attacked by water which after a series of proton transfer step results in a zwitterionic intermediate, containing an ammonium cation and a carboxylate anion. Thermal conditions result in the explosion of carbon dioxide gas and quenching of the ammonium cation to the amine product.[1]

ireland-claisen-rearrangement

https://www.name-reaction.com/ireland-claisen-rearrangement

[ "carbonyl compound" ]

[ "base catalyst", "acid catalyst" ]

[ "ester", "alkene" ]

[]

acid base

The Ireland-Claisen rearrangement is an organic reaction used to convert an allyl ester to a γ,δ-unsaturated carboxyl acid using LDA, TMSCl, and NaOH/H2O. The reaction begins with deprotonation of the α-hydrogen of the ester to form an enolate which then attacks TMSCl to stabilize the charge and produce LiCl salt. The two olefin groups are ideally positioned for aClaisen rearrangement, which results in the formation of a carbonyl group. Deprotection of the TMS group with base and protonation then results in the final carboxylic acid product.[1][2][3]

johnson-claisen-rearrangement

https://www.name-reaction.com/johnson-claisen-rearrangement

[ "alcohol", "carbonyl compound" ]

[ "acid catalyst", "alcohol" ]

[ "ester", "alkene" ]

[]

The Johnson-Claisen rearrangement is an organic reaction where an allylic alcohol is heated with trialkyl orthoacetate under midly acidic conditions to produce a γ,δ-unsaturated ester. The reaction begins with protonation of one of the alkoxide groups of the orthoacetate. The protonated alkoxide is then released as a molecule of alcohol and forms an oxonium cation which is then attached by the alcohol. Proton transfer steps then follow, protonating another alkoxide group, that is again lost as alcohol and forms another oxonium cation. A deprotonation step then produces a 1,5 diene intermediate which undergoes a Claisen sigmatropic rearrangement to provide the final γ,δ-unsaturated ester product.[1]

jones-oxidation

https://www.name-reaction.com/jones-oxidation

[ "alcohol", "carbonyl compound" ]

[ "acid catalyst", "alcohol" ]

[]

acid

The Jones oxidation is an organic reaction used to oxidize alcohols using chromic trioxide and acid in water. A primary alcohol is oxidized to an aldehyde or all the way to a carboxylic acid, while a secondary alcohol to a ketone. The mechanism begins with the reaction of CrO3with acid (often H2SO4) to form chromic acid or dichromic acid in more concentrated solutions. The alcohol oxidation then occurs with chromic acid which in turn gets reduced in the process.[1]

knoevenagel-condensation

https://www.name-reaction.com/knoevenagel-condensation

[ "carbonyl compound" ]

[ "base catalyst" ]

[ "alkene" ]

[]

catalyst base

The Knoevenagel condensation is an organic reaction used to convert an aldehyde or ketone and an activated methylene to a substituted olefin using an amine base as a catalyst. The reaction begins by deprotonation of the activated methylene by the base to give a resonance stabilized enolate. The amine catalyst also reacts with the aldehyde or ketone to form an iminium ion intermediate, which then gets attacked by the enolate. The intermediate compound formed gets deprotonated by the base to give another enolate while the amine of the intermediate gets protonated. A rearrangement then ensues which releases the amine base, regenerates the catalyst, and yields the final olefin product.[1]

knorr-pyrazole-synthesis

https://www.name-reaction.com/knorr-pyrazole-synthesis

[ "carbonyl compound" ]

[ "base catalyst", "acid catalyst" ]

[ "ester" ]

[]

acid catalyst

The Knorr pyrazole synthesis is an organic reaction used to convert a hydrazine or its derivatives and a 1,3-dicarbonyl compound to a pyrazole using an acid catalyst. The mechanism begins with an acid catalyzed imine formation, where in the case of hydrazine derivatives the attack can happen on either carbonyl carbon and result in two possible products. The other nitrogen of the hydrazine derivative then attacks the other carbonyl group which has also been protonated by the acid and forms a second imine group. This diimine compound gets deprotonated to regenerate the acid catalyst and provide the final pyrazole product.[1]

kolbe-schmitt-reaction

https://www.name-reaction.com/kolbe-schmitt-reaction

[ "alcohol", "carbonyl compound" ]

[ "base catalyst", "acid catalyst" ]

[]

acid base

The Kolbe-Schmitt reaction is an organic reaction used to convert a phenol to a hydroxy benzoic acid using carbon dioxide gas, a base, and acid work-up. The mechanism begins with deprotonation of the phenol by the base to form a phenoxide. The phenoxide rearranges to form a carbonyl group while the aromatic ring attacks the CO2molecule. The attack can happen from either the ortho or para position, which explains the two possible products, and results in the loss of aromaticity of the ring. Another deprotonation by the base regenerates aromaticity and produces the phenoxide again. Protonation of the phenoxide and the carboxy-late anions yield the final ortho- and/or para-hydroxy benzoic acids.[1][2]

kumada-cross-coupling

https://www.name-reaction.com/kumada-cross-coupling

[]

[ "base catalyst", "organometallic reagent" ]

[]

catalyst

The Kumada cross-coupling reaction is the organic reaction of an organohalide with an organomagnesium compound, also known as a Grignard reagent, to give the coupled product using a palladium or nickel catalyst. The palladium catalyzed mechanism begins with oxidative addition of the organohalide to the Pd(0) to form a Pd(II) complex. Transmetalation with the Grignard reagent then follows, where the R group of the Grignard reagent replaces the halide anion on the palladium complex and makes a magnesium(II) halide salt. Reductive elimination then gives the final coupled product, regenerates the catalyst, and the catalytic cycle can begin again.[1]

luche-reduction

https://www.name-reaction.com/luche-reduction

[ "alcohol", "carbonyl compound" ]

[ "acid catalyst", "alcohol" ]

[]

solvent

The Luche reduction is an organic reaction used to convert an α,β-unsaturated ketone to an allylic alcohol using cerium trichloride, sodium borohydride, and an alcohol solvent. The role of the cerium or other lanthanide metals is to coordinate to the alcohol, making its proton more acidic which allows for it to be abstracted by the carbonyl oxygen of the ketone starting material. The NaBH4starting regent also reacts with the cerium activated alcohol to form a series of alkoxyborohydrides and these "hard reagents" result in the 1,2 hydride attack on the protonated carbonyl to give the final allylic alcohol product.[1][2]

mannich-reaction

https://www.name-reaction.com/mannich-reaction

[ "carbonyl compound" ]

[ "base catalyst", "acid catalyst", "organometallic reagent" ]

[]

acid catalyst base

The Mannich reaction is an organic reaction used to convert a primary or secondary amine and two carbonyl compound (one non-enolizable and one enolizable) to a β-amino carbonyl compound, also known as a Mannich base, using an acid or base catalyst. In the acid catalyzed mechanism both carbonyl compounds get protonated at the oxygen. The enolizable carbonyl compound, which has an α-hydrogen, then gets deprotonated to form an enol intermediate. The non-enolizable carbonyl compound reacts with the amine to form an iminium ion. The enol intermediate then attacks the iminium ion which after deprotonation provides the final Mannich base product.[1]

michael-addition

https://www.name-reaction.com/michael-addition

[ "carbonyl compound" ]

[ "base catalyst", "acid catalyst", "organometallic reagent" ]

[ "alkene" ]

[]

acid catalyst base

The Michael addition is an organic reaction used to convert an activated methylene and a conjugated olefin to the corresponding addition product using a base catalyst followed by an acid work-up. The activated methylene is essentially a methylene bonded to electron withdrawing groups that would stabilize the negative change that forms after deprotonation by the base. This deprotonation results in an enolate which in turn does a 1,4 addition to the conjugated olefin. An acid work-up then provides the final Michael addition product.[1]

mitsunobu-reaction

https://www.name-reaction.com/mitsunobu-reaction

[ "alcohol", "carbonyl compound" ]

[ "acid catalyst", "alcohol" ]

[ "ester" ]

[]

acid Acid

The Mitsunobu reaction is an organic reaction used to convert a primary or secondary alcohol into a variety of compounds using DEAD and triphenylphosphine. The final product depends on the acidic reagent (the conjugate acid of the nucleophile). The mechanism begins with attack of PPh3on DEAD which forms a zwitterionic intermediate. This intermediate then deprotonates the acidic compound to reveal the anionic nucleophile. The alcohol starting material then binds to the phosphonium ion and the nucleophile performs a SN2attack to yield the final substitution product with inversion of stereochemistry. The formation of a strong P=O in the by-product drives this reaction forward.[1][2]

mukaiyama-aldol-addition

https://www.name-reaction.com/mukaiyama-aldol-addition

[ "carbonyl compound" ]

[ "base catalyst", "acid catalyst", "organometallic reagent" ]

[]

acid catalyst

The Mukaiyama aldol addition is an organic reaction used to convert an aldehyde and a silyl enol ether to a 1,3 ketol using a Lewis acid catalyst (such as TiCl4), followed by aqueous work-up. The mechanism begins by coordination of the aldehyde's oxygen to Titanium, which activate the carbonyl for attack while also releasing a chloride ion. The chloride attacks the silicon of the silyl enol ether to form TMSCl and an enolate. The enolate then attacks the activated carbonyl and subsequent aqueous work-up provides the final 1,3 ketol product.[1][2]

n

https://www.name-reaction.com/n

[ "carbonyl compound" ]

[ "acid catalyst", "organometallic reagent" ]

[ "ester" ]

[]

acid

negishi-cross-coupling

https://www.name-reaction.com/negishi-cross-coupling

[]

[ "base catalyst" ]

[]

catalyst

The Negishi cross-coupling reaction is the organic reaction of an organohalide with an organozinc compound to give the coupled product using a palladium or nickel catalyst. The palladium catalyzed mechanism begins with oxidative addition of the organohalide to the Pd(0) to form a Pd(II) complex. Transmetalation with the organozinc then follows where the R group of the organozinc reagent replaces the halide anion on the palladium complex and makes a zinc(II) halide salt. Reductive elimination then gives the final coupled product, regenerates the catalyst, and the catalytic cycle can begin again.[1]

oppenauer-oxidation

https://www.name-reaction.com/oppenauer-oxidation

[ "alcohol", "carbonyl compound" ]

[ "base catalyst", "alcohol" ]

[]

catalyst

The Oppenauer oxidation is an organic reaction used to convert a primary or secondary alcohol to a ketone using another excess ketone reagent (such as acetone) and an aluminium triisopropoxide catalyst. The mechanism begins with the alcohol replacing one of the isopropoxide groups on the aluminum to generate isopropanol. Acetone then coordinates to the aluminum complex and a rearrangement reaction occurs which includes a hydride transfer from the alcohol to acetone. This process, which oxidizes the alcohol and reduces the acetone, results in the formation of the final ketone product and regeneration of the aluminum triisopropoxide catalyst.[1]

pauson-khand-reaction

https://www.name-reaction.com/pauson-khand-reaction

[ "unsaturated compound" ]

[ "base catalyst", "organometallic reagent" ]

[ "alkene" ]

[]

catalyst

The Pauson-Khand reaction is an organic reaction used to convert an alkyne and alkene to a substituted cyclopentenone under an atmosphere of carbon monoxide and a dicobalt complex catalyst. This 2+2+1 cycloaddition reaction begins with the addition of the alkyne to the metal complex followed by ligand substitution of the alkene to expel a CO molecule. Alkene insertion follows and a subsequent CO insertion results in the formation of a carbonyl group. A series of reductive eliminations then yield the final cyclopentenone product and regenerates the cobalt catalyst.[1][2][3]

perkin-reaction

https://www.name-reaction.com/perkin-reaction

[ "carbonyl compound" ]

[ "base catalyst", "acid catalyst" ]

[]

acid base

The Perkin reaction is an organic reaction used to convert an aromatic aldehyde and an anhydride to an α,β-unsaturated carboxylic acid using sodium acetate, a base, and an acid work-up. The regiochemistry of the reaction, the relative position of the carboxylic acid and aromatic ring in the final product, can be either E or Z. The mechanism goes through numerous steps including several additions and eliminations.[1]

pictet-spengler-reaction

https://www.name-reaction.com/pictet-spengler-reaction

[ "carbonyl compound" ]

[ "base catalyst", "acid catalyst" ]

[]

acid catalyst

The Pictet-Spengler reaction is an organic reaction used to convert a β-arylenylamine and an aldehyde or ketone to a tetrahydroisoquinoline using an acid catalyst. The mechanism begins with protonation of the carbonyl oxygen by the acid which is subsequently attacked by the amine reagent. Proton transfer steps and the release of a water molecule results in a protonated imine intermediate, which then undergoes a 6-endo-trig cyclization reaction with loss of aromaticity of the aryl ring. A final deprotonation step restores the aromaticity and results in the tetrahydroisoquinoline product.[1]

prins-reaction

https://www.name-reaction.com/prins-reaction

[ "alcohol", "carbonyl compound", "unsaturated compound" ]

[ "organometallic reagent", "alcohol" ]

[ "alkene" ]

[]

The Prins reaction is an organic reaction used to convert an alkene and an aldehyde to a variety of products depending on the reaction conditions. All mechanisms begin with protonation of the aldehyde which is then attacked by the alkene to give a β-hydroxyl carbocation intermediate. Without the addition of other reagents this intermediate will react with water in an elimination reaction to give an allylic alcohol product. If nucleophiles are added to the reaction mixture they would directly attack the carbocation to give an alcohol, while if excess of the aldehyde reagent is used, the reaction will result in a 1,3-dioxane.[1][2]

reformatsky-reaction

https://www.name-reaction.com/reformatsky-reaction

[ "carbonyl compound" ]

[ "acid catalyst", "organometallic reagent" ]

[ "ester" ]

[]

acid

The Reformatsky reaction is an organic reaction used to convert an α-haloester and an aldehyde or ketone to a β-hydroxyester using zinc metal followed by an acid work-up. The reaction begins with oxidative addition of the zinc metal to the carbon-halogen bond of the α-haloester. Two of the resulting compounds coordinate to each other forming a dimer, which then undergoes a rearrangement to give two molecules of O-zinc enolates. The oxygen of the aldehyde or ketone reagent then coordinates to the zinc and another rearrangement ensues which joins the two reagents with a carbon-carbon bond. An acid work-up then cleaves the zinc-oxygen bond to give the final β-hydroxyester product and a zinc(II) salt.[1]

reimer-tiemann-reaction

https://www.name-reaction.com/reimer-tiemann-reaction

[ "alcohol", "carbonyl compound" ]

[ "base catalyst", "acid catalyst" ]

[]

acid base

The Reimer-Tiemann reaction is an organic reaction used to convert a phenol to an o-hydroxy benzalde-hyde using chloroform, a base, and acid work-up. The mechanism begins with abstraction of the proton from chloroform with the base to form a trichlorocarbanion which spontaneously loses a chloride ion to form a neutral dichlorocarbene. The base also deprotonates the phenol reagent which then attacks the carbene. A series of steps and a final acid work-up result in the o-hydroxy benzaldehyde product.[1][2][3]

ritter-reaction

https://www.name-reaction.com/ritter-reaction

[ "alcohol", "carbonyl compound", "unsaturated compound" ]

[ "acid catalyst", "organometallic reagent", "alcohol" ]

[ "amide", "alkene" ]

[]

acid

The Ritter reaction is an organic reaction used to convert a nitrile and a carbocation precursor (such as a substituted olefin or tertiary alcohol) to an amide using a strong acid and water. The mechanism begins with the formation of the carbocation from the reaction of the acid with the carbocation precursor. The nitrile then attacks the carbocation to form a nitrilium ion. Water hydrolysis and a series of proton transfer steps then yield the final amide product.[1][2]

robinson-annulation

https://www.name-reaction.com/robinson-annulation

[ "carbonyl compound" ]

[ "base catalyst", "organometallic reagent" ]

[ "alkene" ]

[]

base

The Robinson annulation is an organic reaction used to convert a ketone and an α,β-unsaturated ketone to a cyclohexenone using base. The mechanism begins with deprotonation with the base of the α-hydrogen of the ketone to form an enolate. The enolate then does a 1,4 addition to the conjugated olefin (Michael addition), which then abstracks a proton from water to form a diketone. Deprotonation of the other α-hydrogen with base forms another enolate which then does in intramolecular attack on the ketone group to give a cyclic alkoxy intermediate. Protonation of the alkoxy and a final elimination step result in the cyclo-hexenone product.[1]

sandmeyer-reaction

https://www.name-reaction.com/sandmeyer-reaction

[]

[ "base catalyst" ]

[]

catalyst

The Sandmeyer reaction is an organic reaction used to convert an aryl diazonium salt to an aryl halide using a copper(I) halide catalyst. The mechanism begins with a single electron transfer (SET) from the copper to the diazonium to form a neutral diaso radical and copper(II) halide. The diazo radical then releases a molecule of nitrogen gas to form an aryl radical. The aryl radical reacts with the copper(II) halide to regenerate the copper(I) halide catalyst and yield the final aryl halide product.[1][2]

schmidt-reaction

https://www.name-reaction.com/schmidt-reaction

[ "carbonyl compound" ]

[ "base catalyst", "acid catalyst" ]

[]

acid catalyst

The Schmidt reaction is an organic reaction used to convert hydrazoic acid to a variety of products using an acid catalyst. The mechanism shown is for an aldehyde regent but it can be easily extended to the other regents. The reaction begins with abstraction of a proton from the acid by the aldehyde or other reagent to activate it for future attack. The generated water molecule then abstracts the proton from hydrazoic acid to regenerate the acid and produce an azide anion which then attacks the activated reagent. A series of steps and the release of a molecule of nitrogen gas result in the final product.[1][2]

schotten-baumann-reaction

https://www.name-reaction.com/schotten-baumann-reaction

[ "alcohol", "carbonyl compound" ]

[ "base catalyst", "alcohol" ]

[ "amide", "ester" ]

[]

base

The Schotten-Baumann reaction is an organic reaction used to convert an acyl halide or anhydride to an amide if reacted with an amine and base, or an ester if reacted with an alcohol and base. The reaction with the amine begins with the nitrogen attacking the carbonyl carbon of the acyl halide which rearranges to kick out the halide. Deprotonation with the base then provides the final amide product. The reaction with the alcohol would happen in a similar fashion.[1][2]

sharpless-epoxidation

https://www.name-reaction.com/sharpless-epoxidation

[ "alcohol" ]

[ "base catalyst", "alcohol" ]

[]

catalyst

The Sharpless epoxidation is an organic reaction used to steroselectively convert an allylic alcohol to an epoxy alcohol using a titanium isopropoxide catalyst, t-butyl hydroperoxide (TBHP), and a chiral diethyl tartrate (DET). The mechanism begins with the displacement of the isopropoxide ligands on the titanium by DET, TBHP, and finally by the allylic alcohol reagent. This titanium complex is believed to exist as a dimer, but for simplicity is shown as a monomer in the mechanism. Oxidation of the olefin with TBHP then occurs where the chiral DET dictates the face of attack and leads to a steroselective epoxy alcohol.[1]

sonogashira-cross-coupling

https://www.name-reaction.com/sonogashira-cross-coupling

[ "unsaturated compound" ]

[ "base catalyst" ]

[ "alkene" ]

[]

catalyst base

The Sonogashira cross-coupling reaction is the organic reaction of an organohalide with a terminal alkyne to give the coupled product using a palladium catalyst, a copper catalyst, and base. The palladium cataly-zed mechanism begins with oxidative addition of the organohalide to the Pd(0) to form a Pd(II) complex. Transmetalation with the organocopper reagent, formed from the terminal alkyne and the copper catalyst, then follows. The alkynyl anion replaces the halide on the palladium complex and regenerates the copper halide catalyst. Reductive elimination then gives the final coupled product, regenerates the palladium catalyst, and the catalytic cycle can begin again.[1]

staudinger-reaction

https://www.name-reaction.com/staudinger-reaction

[ "triphenylphosphine", "as" ]

[ "is", "an" ]

[ "to", "pr" ]

[]

The Staudinger reaction is an organic reaction used to convert an organic azide to a primary amine using a PR3compound (such as triphenylphosphine) and water. The mechanism begins with attack of the phos-phorus on the far nitrogen of the organic azide to give a phosphazide intermediate. This intermediate then goes through a rearrangement that releases a molecule of nitrogen gas and forms a N-P ylide. The molecule of water then attacks the phosphorus atom and a series or proton transfer steps follow to result in the formation of the final primary amine and a triphenylphosphine oxide by-product.[1]

stille-cross-coupling

https://www.name-reaction.com/stille-cross-coupling

[ "carbonyl compound" ]

[ "base catalyst", "acid catalyst" ]

[]

acid catalyst

The Stille cross-coupling reaction is the organic reaction of an organohalide with an organostannane com-pound to give the coupled product using a palladium catalyst. The mechanism begins with oxidative add-ition of the organohalide to the Pd(0) to form a Pd(II) complex. Transmetalation with the organostannane then follows where the R group of the organostannane reagent replaces the halide anion on the palladium complex. Reductive elimination then gives the final coupled product, regenerates the palladium catalyst, and the catalytic cycle can begin again.[1][2]

strecker-amino-acid-synthesis

https://www.name-reaction.com/strecker-amino-acid-synthesis

[ "carbonyl compound" ]

[ "base catalyst", "acid catalyst" ]

[ "amide" ]

[]

acid catalyst

The Strecker amino acid synthesis is an organic reaction used to convert an aldehyde or ketone and a pri-mary amine or ammonia to an α-amino acid using a metal cyanide, acid catalyst, and water. The mecha-nism begins with the acid catalyzed reaction of the carbonyl with the amine to give the corresponding imine. The imine is then attacked by the cyanide to provide a nitrile intermediate. The nitrile gets protonated by the acid, is attacked by a molecule of water and after a series of proton transfer steps results in an amide intermediate. In the reaction's acid conditions, the amide gets protonated and the amine group is displaced by water to eventually yield the carboxylic acid group and the final amino acid product.[1][2]

suzuki-cross-coupling

https://www.name-reaction.com/suzuki-cross-coupling

[]

[ "base catalyst" ]

[]

catalyst base

The Suzuki cross-coupling reaction is the organic reaction of an organohalide with an organoborane to give the coupled product using a palladium catalyst and base. The mechanism begins with oxidative addition of the organohalide to the Pd(0) to form a Pd(II) complex. A molecule of the hydroxide or alkoxide base then replaces the halide on the palladium complex, while another adds to the organoborane to form a borate regent making its R group more nucleophilic. Transmetalation with the borate then follows where its R group replaces the halide anion on the palladium complex. Reductive elimination then gives the final coupled product, regenerates the palladium catalyst, and the catalytic cycle can begin again.[1][2]

swern-oxidation

https://www.name-reaction.com/swern-oxidation

[ "alcohol", "carbonyl compound" ]

[ "alcohol" ]

[]

The Swern oxidation is an organic reaction used to convert a primary alcohol to an aldehyde and a secon-dary alcohol to a ketone using DMSO, oxalyl chloride, and triethylamine. The mechanism begins with the activation of DSMO with oxalyl chloride which is then attacked by a chloride anion to form a chlorosulfo-nium cation and release both CO and CO2gas. The alcohol then attacks the chlorosulfonium salt which releases the chloride anion and forms an alkoxysulfonium cation. Triethylamine then deprotonates the alkoxysulfonium at the alpha position to form a alkoxysulfonium ylide. A rearrangemnt then ensues which releases a molecule of dimethyl sulfide gas and results in the final aldehyde or ketone product.[1][2]

ullmann-reaction

https://www.name-reaction.com/ullmann-reaction

[ "halide", "alkyl halide" ]

[ "as", "or" ]

[ "is", "an" ]

[]

The Ullmann reaction is an organic reaction used to couple two molecules of aryl halide to form a biaryl using copper metal and thermal conditions. The mechanism for the Ullmann reaction is not fully under-stood but there are two popular mechanisms. The radical mechanism begins with a single electron transfer (SET) from the copper metal to the alkyl halide to form an aryl radical. Two aryl radical then react to form the final biaryl product. The second proposed mechanism begins with oxidative addition of the copper to the aryl halide followed by a SET to form an organocuprate reagent. The organocuprate performs another oxidative addition on an aryl halide and after reductive elimination results in the final biaryl product.[1][2]

vilsmeier-haack-reaction

https://www.name-reaction.com/vilsmeier-haack-reaction

[ "carbonyl compound" ]

[ "acid catalyst" ]

[]

acid

The Vilsmeier-Haack reaction is an organic reaction used to convert an electron rich aromatic ring to an aryl aldehyde using DMF, an acid chloride, and aqueous work-up. The mechanism begins with the reaction of DMF with the acid chloride to form an iminium salt known as the "Vilsmeier reagent". The electron rich aromatic ring then attacks the iminium ion with loss of aromaticity. A deprotonation step restores aromati-city, which is followed by the release of a chloride ion to form another iminium intermediate. Aqueous work-up then leads to the aryl aldehyde final product.[1]

wagner-meerwein-rearrangement

https://www.name-reaction.com/wagner-meerwein-rearrangement

[ "alcohol", "carbonyl compound" ]

[ "base catalyst", "acid catalyst", "alcohol" ]

[ "alkene" ]

[]

acid catalyst

The Wagner-Meerwein rearrangement is an organic reaction used to convert an alcohol to an olefin using an acid catalyst. The mechanism begins with protonation of the alcohol by the acid which is then released as water to forms a carbocation. A 1,2-shift then occurs to form a more substituted and stabilized carbo-cation. A final deprotonation with water produces the final olefin product and regenerates the acid catalyst.[1][2]

williamson-ether-synthesis

https://www.name-reaction.com/williamson-ether-synthesis

[ "alcohol" ]

[ "base catalyst", "alcohol" ]

[]

base

The Williamson ether synthesis is an organic reaction used to convert an alcohol and an alkyl halide to an ether using a base such as NaOH. The mechanism begins with the base abstracting the proton from the alcohol to form an alkoxide intermediate. The alkoxide then attacks the alkyl halide in a nucleophilic substi-tution reaction (SN2), which results in the formation of the final ether product and a metal halide by-product.[1][2]

wittig-reaction

https://www.name-reaction.com/wittig-reaction

[ "carbonyl compound", "aldehyde", "ketone" ]

[ "phosphorus ylide", "wittig reagent" ]

[]

[ "triphenylphosphine oxide", "Ph3P=O" ]

base

The Wittig reaction is an organic reaction used to convert a primary or secondary alkyl halide and an aldehyde or ketone to an olefin using triphenylphosphine and base. The mechanism beings with attack of the PPH3on the alkyl halide which releases the halide anion and forms a phosphonium ion. The base then deprotonates at the alpha position to afford a phosphonium ylide. The ylide subsequently attacks the alde-hyde or ketone to form a zwitterion where the oxygen anion then attacks the phosphonium cation to form an oxaphosphetane. A rearrangement then generates the final olefin product and releases a triphenylphos-phine oxide by-product whose formation of a strong P=O bond is the driving force for this reaction.[1][2]

wolff-rearrangement

https://www.name-reaction.com/wolff-rearrangement

[ "carbonyl compound" ]

[ "base catalyst" ]

[]

catalyst

The Wolff rearrangement is an organic reaction used to convert an α-diazo ketone to a ketene using a silver oxide catalyst, light, or thermal conditions. The mechanism of the Wolff rearrangement is essentially one step which is initiated by the catalyst. The reaction involves a 1,2-shift to form the ketene product and release a molecule of nitrogen gas. Subsequent attacks by nucleophiles to the ketene formed are also considered Wolff rearrangement.[1]

wolff-kishner-reduction

https://www.name-reaction.com/wolff-kishner-reduction

[ "carbonyl compound" ]

[ "base catalyst" ]

[]

catalyst base

The Wolff-Kishner reduction is an organic reaction used to convert an aldehyde or ketone to an alkane using hydrazine, base, and thermal conditions. The mechanism begins with the attack of hydrazine of the aldehyde or ketone for form an imine. Proton transfer steps then result in the formation of a N=N bond. Deprotonation of the nitrogen and a rearrangement reaction result in the formation of a carbanion and the release of nitrogen gas. The carbanion then picks up a proton from water to regenerate the base catalyst and provides the final alkane product.[1][2]

wurtz-reaction

https://www.name-reaction.com/wurtz-reaction

[ "alkyl halide", "halide" ]

[ "as", "is" ]

[ "an", "to" ]

[]

The Wurtz reaction is an organic reaction used to couple two alkyl halides to form an alkane using sodium metal. The mechanism begins with a single electron transfer (SET) from sodium metal to the alkyl halide, which dissociates to form an alkyl radical and sodium halide salt. Another molecule of sodium performs another SET to the alkyl radical to form a nucleophilic carbanion. The carbanion then attacks another molecule of alkyl halide in a nucleophilic substitution reaction (SN2) to form the final coupled product and another molecule of sodium halide salt.[1][2]

yamaguchi-esterification

https://www.name-reaction.com/yamaguchi-esterification

[ "alcohol", "carbonyl compound" ]

[ "acid catalyst", "alcohol" ]

[ "ester" ]

[]

acid

The Yamaguchi esterification is an organic reaction used to convert a carboxylic acid and an alcohol to an ester using triethylamine, the Yamaguchi reagent, and DMAP. The mechanism begins with deprotonation of the carboxylic acid by Et3N to form a carboxylate anion which then attacks the Yamaguchi reagent. The resultant acid anhydride get attacked by DMAP to form a better leaving group which is then displaced by the alcohol reagent. A final deprotonation step results in the ester product.[1]

0-9[edit]

https://en.wikipedia.org/w/index.php?title=List_of_organic_reactions&action=edit&section=1

[ "to", "us" ]

[ "log", "in" ]

[]

1,2-Wittig rearrangement

https://en.wikipedia.org/wiki/1,2-Wittig_rearrangement

[ "to", "us" ]

[ "log", "in" ]

[]

1,3-Dipolar cycloaddition

https://en.wikipedia.org/wiki/1,3-Dipolar_cycloaddition

[ "to", "us" ]

[ "log", "in" ]

[]

2,3-Wittig rearrangement

https://en.wikipedia.org/wiki/2,3-Wittig_rearrangement

[ "to", "us" ]

[ "log", "in" ]

[]

A[edit]

https://en.wikipedia.org/w/index.php?title=List_of_organic_reactions&action=edit&section=2

[ "to", "us" ]

[ "log", "in" ]

[]

Abramovitch�Shapiro tryptamine synthesis

https://en.wikipedia.org/wiki/Tryptamine

[ "to", "us" ]

[ "log", "in" ]

[]

Acetalisation

https://en.wikipedia.org/wiki/Acetalisation

[ "to", "us" ]

[ "log", "in" ]

[]

Acetoacetic ester condensation

https://en.wikipedia.org/wiki/Acetoacetic_ester_condensation

[ "to", "us" ]

[ "log", "in" ]

[]

Achmatowicz reaction

https://en.wikipedia.org/wiki/Achmatowicz_reaction

[ "to", "us" ]

[ "log", "in" ]

[]

Acylation

https://en.wikipedia.org/wiki/Acylation

[ "to", "us" ]

[ "log", "in" ]

[]

Acyloin condensation

https://en.wikipedia.org/wiki/Acyloin_condensation

[ "to", "us" ]

[ "log", "in" ]

[]

Adams' catalyst

https://en.wikipedia.org/wiki/Adams%27_catalyst

[ "to", "us" ]

[ "log", "in" ]

[]

Adams decarboxylation

https://en.wikipedia.org/wiki/Adams_decarboxylation

[ "to", "us" ]

[ "log", "in" ]

[]

Adkins catalyst

https://en.wikipedia.org/wiki/Adkins_catalyst

[ "to", "us" ]

[ "log", "in" ]

[]

Adkins�Peterson reaction

https://en.wikipedia.org/wiki/Adkins%E2%80%93Peterson_reaction

[ "to", "us" ]

[ "log", "in" ]

[]

Akabori amino acid reaction

https://en.wikipedia.org/wiki/Akabori_amino_acid_reaction

[ "to", "us" ]

[ "log", "in" ]

[]

Alcohol oxidation

https://en.wikipedia.org/wiki/Alcohol_oxidation

[ "to", "us" ]

[ "log", "in" ]

[]

Alder�Stein rules

https://en.wikipedia.org/wiki/Alder%E2%80%93Stein_rules

[ "to", "us" ]

[ "log", "in" ]

[]

Aldol addition

https://en.wikipedia.org/wiki/Aldol_addition

[ "to", "us" ]

[ "log", "in" ]

[]

Aldol condensation

https://en.wikipedia.org/wiki/Aldol_condensation

[ "to", "us" ]

[ "log", "in" ]

[]

Algar�Flynn�Oyamada reaction

https://en.wikipedia.org/wiki/Algar%E2%80%93Flynn%E2%80%93Oyamada_reaction

[ "to", "us" ]

[ "log", "in" ]

[]

Alkylimino-de-oxo-bisubstitution

https://en.wikipedia.org/wiki/Alkylimino-de-oxo-bisubstitution

[ "to", "us" ]

[ "log", "in" ]

[]

Alkyne trimerisation

https://en.wikipedia.org/wiki/Alkyne_trimerisation

[ "to", "us" ]

[ "log", "in" ]

[]

Alkyne zipper reaction

https://en.wikipedia.org/wiki/Alkyne_zipper_reaction

[ "to", "us" ]

[ "log", "in" ]

[]

Allan�Robinson reaction

https://en.wikipedia.org/wiki/Allan%E2%80%93Robinson_reaction

[ "to", "us" ]

[ "log", "in" ]

[]