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940dcd98_Flashcards_about_orgoexam2__Answer
[Question] electron withdrawing groups are acid ___ [Answer]
strengthening
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] electron donating groups are acid ___ [Answer]
weakening
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] solvation and proton transfer can be affected by [Answer]
steric effects
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] the more easy an alkoxide ion is solvated, the [Answer]
more its formation is energetically favored
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] Phenols are much more acidic than alcohols due to [Answer]
resonance stabilization of the phenoxide ion. Phenols react with NaOH solutions (but alcohols do not), forming salts that are soluble in dilute aqueous solution.
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] A phenolic compound can be separated from an organic solution by [Answer]
extraction into basic aqueous solution and is isolated after acid is added to the solution
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] Phenols with nitro groups at the ortho and para positions are much stronger acids because [Answer]
of the resonance stabilization of the alkoxide anion.
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] What other groups besides nitro can stabilize the alkoxide anion? [Answer]
-SO3R & -CO2R
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] hydration: [Answer]
regiospecific(limited) but not stereospecific
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] hydroboration/oxidation: [Answer]
syn, non-Markovnikov hydration
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] oxymercuration/reduction: [Answer]
Markovnikov hydration
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] Reduction of a carbonyl compound generally yields: [Answer]
an alcohol
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] reduction of aldehydes gives [Answer]
primary alcohols
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] reduction of ketones gives [Answer]
secondary alcohols
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] NaBH4 is not [Answer]
sensitive to moisture and does not reduce other common functional groups. Adds the equivalent of "H"
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] LiAlH4 is [Answer]
more powerful than NaBH4, less specific, and very reactive with water. Adds the equivalent of "H"
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] Carboxylic acids and esters are reduced using LiAlH4 to give [Answer]
primary alcohols(NaBH4 is not effective)
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] Alkyl, aryl, and vinylic halides react with Mg in ether or tetrahydrofuran to generate [Answer]
Grignard Reagents. These Grignard reagents in turn react with carbonyl compounds to yield alcohols
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] Grignard Reagents act as [Answer]
nucleophilic carbanions in adding to the carbonyl group. The intermediate alkoxide is then protonated to produce the alcohol
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] to produce only an aldehyde, milder oxidizing agents must be used (PCC, C5H6NCrO3Cl) pyridium chlorochromate in dichloromethane bc [Answer]
other stronger oxidizing agents will oxidize the intermediate aldehydes into carboxylic acids
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] oxidizing agents used by chemists, such as chromate and permanganate salts are not [Answer]
present in living systems
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] oxidation of a secondary alcohol produces [Answer]
a ketone as the product
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] PCC is used to oxidize [Answer]
sensitive secondary alcohols at low temperatures
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] Swern Oxidiztion is carried out in [Answer]
DMSO not an Aqueous solvent,so the product stops at the aldehyde. also, the reaction does not involve chromium-based reagents which are toxic
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] tertiary alcohols react with HCl or HBr by [Answer]
SN1 through carbocation intermediate to form alkyl halides
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] primary and secondary alcohols are converted into halides by treatment with [Answer]
SOCl2 or PBr3 via SN2 mechanism
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] Reacting an alcohol with p-toluenesulfonyl chloride (tosyl chloride, p-TsCl)in pyridine yields [Answer]
alkyl tosylates, ROTs. The formation of the tosylate does not involve the C–O bond so configuration at a chirality center is maintained. Alkyl tosylates react like alkyl halides, i.e. good leaving groups.
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] The SN2 reaction of an alcohol via a tosylate produces [Answer]
an inversion at the chirality center.
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] The SN2 reaction of an alcohol via a halide proceeds with [Answer]
two inversions, giving the product the same arrangement as the starting alcohol
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] an alkene can be formed from an alcohol by [Answer]
a dehydration reaction to create a pi bond. specific reagents are needed to facilitate this elimination (usually strong acid)
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] tertiary alcohols are readily [Answer]
dehydrated with acid
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] secondary alcohols require what for dehydration? [Answer]
severe conditions (75% H2SO4, 100C) and sensitive molecules dont survive
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] primary alcohols require what for dehydration? [Answer]
very harsh conditions; they are impractical and usually rearrange to form a more stable carbocation. reactivity is the resul of the nature of the carbocation intermediate
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] Phosphorus oxychloride in the amine solvent pyridine can lead to [Answer]
dehydration of secondary and tertiary alcohols at low temperatures. This reaction proceeds via an E2 mechanism from an intermediate ester of POCl2
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] hydroxyl groups can easily [Answer]
transfer their proton to a basic reagent
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] Converting the hydroxyl to a (eventually removable) functional group without an acidic proton [Answer]
protects the alcohol
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] Reaction with chlorotrimethylsilane in the presence of base yields [Answer]
an unreactive trimethylsilyl (TMS) ether. The ether can be cleaved with acid or with fluoride ion to regenerate the alcohol.
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] The hydroxyl group of phenols is strongly activating, making phenols [Answer]
good substrates for electrophilic halogenation, nitration, sulfonation, and Friedel–Crafts reactions (or any electrophilic substitution).
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] Reaction of a phenol with a strong oxidizing agent will yield [Answer]
a quinone
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] Fremy's salt [(KSO3 )2 NO] works under mild conditions through [Answer]
a radical mechanism
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] Ubiquinones mediate electron-transfer processes involved in energy production through [Answer]
their redux reactions
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] Ether [Answer]
has two organic groups (alkyl, aryl or vinyl) bonded to the same oxygen atom R-O-R'
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] diethyl ether can be prepared by [Answer]
sulfuric acid catalyzed dehydration of ethanol or other primary alcohols. This is a good way to prepare symmetrical ethers
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] Williamson Ether Synthesis [Answer]
reaction of metal alkoxides and primary alkyl halides and tosylates. Best method for the preparation of ethers.Best way to prepare unsymmetrical ethers, but is a good way to prepare symmetrical ethers too
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] Alkoxides made by reacting an alcohol with [Answer]
a strong base like NaH
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] Reaction of alcohols with Ag2O directly with alkyl halide forms [Answer]
ether in one step. Glucose reacts with excess iodomethane in the presence of Ag2O to generate a pentaether in 85% yield
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] Alkoxymercuration of Alkenes [Answer]
react alkene with an alcohol and mercuric acetate or trifluoroacetate. demercuration with NaBH4 yields an ether. overall Markovnikov addition of alcohol to alkene.
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] Mechanicallistically, the alkoxymercuration of alkenes is analagous to [Answer]
the hydration of an alkene
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] reactions of ethers: acidic cleavage [Answer]
ethers are generally unreactive. strong acid will cleave an ether at elevated temperature. HI, HBr produce an alkyl halide from less hindered component by SN2(tertiary ethers undergo SN1)
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] The protonated ether can undergo substitution reactions because [Answer]
a good leaving group (ROH) has been generated.
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] The neutral ether is unreactive because [Answer]
it has a very poor leaving group (RO-)
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] chemically inert ethers are commonly used as organic solvents because [Answer]
they can dissolve both polar and non-polar organics and because they are unreactive with most reagents except strong acids.
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] autoxidation is an unwanted side reaction that makes the handling of some ethers potentially dangerous due to [Answer]
the formation of explosive hydroperoxides
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] Cleavage of Ethers by HX: primary and methyl ethers [Answer]
cleavage occurs by an SN2 mechanism. Initial attack occurs on the less hindered carbon. The alcohol formed in the first step of the reaction will react further with HX. reaction is slow and requires high temperatures and concentrated acids
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] Cleavage of secondary, tertiary, allylic and benzylic ethers [Answer]
The cleavage occurs by an SN1 mechanism with formation of the more stable carbocation. the reaction occurs at lower temperatures so the alcohol formed during the first step may not react further. E1 elimination will complete the substitution process.
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] Autoxidation of ethers [Answer]
Autoxidation is a particular problem for 2° ethers but also occurs with common laboratory solvents such as diethyl ether and THF.
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] Reactions of ethers: claisen rearrangement [Answer]
specific to allyl aryl ethers, ArOCH2CH=CH2. heating to 200-250C leads to an o-allylphenol. result is alkylation of the phenol in an ortho position
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] Cyclic ethers behave like acyclic ethers except if [Answer]
the ring is 3-membered
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] dioxane and tetrahydrofuran are used as [Answer]
solvents
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] Cyclic ethers: epoxides (oxiranes) [Answer]
three membered ring ether is called an oxirane or an epoxide.
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] ethylene oxide is industrially important as an intermediate fro several processes. it is prepared by [Answer]
a reaction of ethylene with oxygen at 300C and silver oxide catalyst
[]
Flashcards about orgoexam2
Answer
http://www.studystack.com/flashcard-873938
16/1438042987866.61_20150728002307-00178-ip-10-236-191-2_740545086_3.json
940dcd98_Flashcards_about_orgoexam2__Answer
[Question] reactions of cyclic ethers [Answer]
5 and 6 membered rings such as THF and THP are as unreactive as their acyclic analogues.
[]
Flashcards about orgoexam2
Answer
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[Question] 3 membered rings are uniquely reactive, much like cyclopropanes are much more reactive than ordinary alkanes. the reason for the reactivity is the same in both cases: [Answer]
Any reaction that cleaves the ring releases about 25 kcal/mol of bond strain. This can make otherwise endergonic reactions thermodynamically feasible; can speedup the rate of reactions
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[Question] the release of strain energy makes an epoxide [Answer]
much more reactive than an acyclic ether
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[Question] Epoxides from halohydrins [Answer]
Addition of HO-X to an alkene gives a halohydrin. Treatment of a halohydrin with base gives an epoxide via intermolecular willamson ether synthesis. The nucleophile and leaving group muct be able to be anti
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[Question] Preparation of Epoxides using a Peroxyacid [Answer]
treat an alkene with a peroxyacid, mCPBA is the most common
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[Question] Reactions of epoxides: acid catalyzed Ring-opening [Answer]
water adds to epoxides with dilute acid at room temperature to give a 1,2-diol. Mechanism: acid protonates oxygen and water adds to the opposite side(trans addition)
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[Question] halohydrins from epoxides [Answer]
anhydrous HF,HBr, HCl, or HI combines with an epoxide and gives a trans product
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[Question] regiochemistry of acid-catalyzed opening of epoxides [Answer]
Nucleophile preferably adds to less hindered site if primary and secondary C’s. Beware however, if there is a tertiary center the ring will open to generate the tertiary carbocation and the nucleophile will add there.
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Flashcards about orgoexam2
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[Question] rapid acid catalyzed ring cleavage of epoxides [Answer]
The stereoselectivity is consistent with an ordinary SN 2 reaction, but the regiochemistry is not.
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Flashcards about orgoexam2
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[Question] the transition state for an epoxide opening [Answer]
The transition state for the reaction has an unbalanced structure with bond cleavage ahead of bond formation.
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Flashcards about orgoexam2
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[Question] nucleophilic addition (and ring opening) TO EPOXIDES [Answer]
Epoxides are subject to SN 2 reactions under conditions in which other ethers are inert. The attack occurs at the less hindered carbon and with inversion of configuration at the reacting carbon.
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[Question] base catlayzed epoxide opening: SN2 [Answer]
strain of the three membered ring is relieved on ring opening. hydroxide cleaves epoxides at elevated temperatures to give trans 1,2-diols
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[Question] organometallic addition to epoxides [Answer]
reactions with nucleophilic organo metallics RLi and RMgX are important C-C bond forming reactions. The configuration of the carbon that does not react remains unchanged
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[Question] epoxides in biological systems: arene oxides [Answer]
arene oxides are subject to two different reactions, the first is the nucleophilic attack like other epoxides and the second is a rearrangement via the NIH shift to make phenols
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[Question] chemical carcinogens are electrophiles that react with [Answer]
nucleophilic sites on the DNA bases, particularly deoxyguanosine
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[Question] crown ethers [Answer]
specifically bind certain metal ions or organic molecules to form a host-guest complex, an example of molecular recognition.
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[Question] crown ethers can serve as phase-transfer catalysts by bringing ionic salts into non-polar solvents that they [Answer]
are not normally soluble in. The anions that are brought into solution are very weakly solvated. these weakly solvated anions may react at an increased rate in these solvents as nucleophiles, redox reagents etc.
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[Question] thiols are sulfure analogs of alcohols [Answer]
thiols (RSH) named with the suffix thiol. SH group is called a mercapto group
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[Question] although they have similar chemistry to alcohols, thiols have unique properties that are distinct from alcohols [Answer]
In protic solvents RS- are better nucleophiles than the corresponding RO- because they are less heavily solvated.
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[Question] RSH2+ are not usually used as substrates in substitution reactions because [Answer]
H2S is not as good a leaving group as H2O and RSH is more difficult to protonate.
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[Question] thiols: formation and reaction [Answer]
From alkyl halides by displacement with a sulfur nucleophile such as –SH or S-2 . The alkylthiol product can undergo further reaction with the alkyl halide to give a symmetrical sulfide, giving a poorer yield of the thiol.
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[Question] thiols: formation and reaction 2 [Answer]
Thioamides may be hydrolyzed to yield thiols, but very slow and relatively basic conditions are necessary.
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[Question] using thiourea to form alkylthiols [Answer]
Thiols can undergo further reaction with the alkyl halide to give dialkyl sulfides. For a pure alkylthiol use thiourea (NH2 (C=S)NH2 ) as the nucleophile.
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[Question] using thiourea to form alkylthiols 2 [Answer]
This gives an intermediate alkylisothiourea salt, which is hydrolyzed cleanly to the alkyl thiourea.
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[Question] oxidation of thiols to disulfates [Answer]
Reaction of an alkyl thiol (RSH) with bromine or iodine gives a disulfide (RSSR). The thiol is oxidized in the process and the halogen is reduced.
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[Question] sulfides [Answer]
Thiolates (RS- ) are formed by the reaction of a thiol with a base. Thiolates react with primary or secondary alkyl halide to give sulfides (RSR’). Thiolates are excellent nucleophiles and react with many electrophiles.
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[Question] More on the Synthesis of Thioethers (Sulfides). [Answer]
Reaction is analogous to the Williamson ether synthesis. Since RS- is a relatively weak base it is less likely to cause elimination reactions than is RO- . R' should still be as unhindered as possible.
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[Question] The thioether is far more [Answer]
nucleophilic than an ether is
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[Question] Sulfur compounds are more nucleophilic than their oxygen-compound analogs. [Answer]
The 3p electrons valence electrons (on S) are less tightly held than 2p electrons (on O). Sulfides react with primary alkyl halides (SN 2) to give trialkylsulfonium salts (R3 S+ )
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[Question] oxidation reactions of sulfides/thioethers [Answer]
Sulfides are easily oxidized with H2O2 to the sulfoxide (R2 SO). Oxidation of a sulfoxide with a peroxyacid yields a sulfone (R2 SO2 ). Dimethyl sulfoxide (DMSO) is often used as a polar aprotic solvent.
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[Question] Aldehydes and Ketones [Answer]
Aldehydes (RCHO) and ketones (R2 CO) are characterized by the the carbonyl functional group (C=O) The compounds occur widely in nature as intermediates in metabolism and biosynthesis
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[Question] Class I carbonyl compounds [Answer]
Class I carbonyl compounds have groups that can be replaced by a nucleophile. A carbonyl group has a C=O. An acyl group is an alkyl or aryl group attached to the carbonyl group.
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[Question] Class I carbonyl compounds 2 [Answer]
The group attached to the carbonyl group strongly affects the reactivity of the carbonyl compound.
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[Question] Class I carbonyl compounds 3 [Answer]
carboxylic acid (O=COH), ester(OR), acid anhydride(O[C=O]R), acyl halides(O=CX), amides(NH2, NHR, NR2)
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[Question] Class II carbonyl compounds [Answer]
s have groups that cannot be replaced by a nucleophile. These are commonly aldehydes and ketones. The H bonded to the acyl group of an aldehyde or the R group bonded to the acyl group of a ketone cannot be readily replaced by a nucleophile.
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[Question] structure of a carbonyl carbon [Answer]
the carbonyl carbon in carboxylic acids and carboxylic acid derivatives is sp2 hybridized, has bond angles of 120 and has a trigonal planar shape
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[Question] naming aldehydes and ketones [Answer]
Aldehydes are named by replacing the terminal -e of the corresponding alkane name with –al The parent chain must contain the ⎯CHO group The ⎯CHO carbon is numbered as C1 If the ⎯CHO group is attached to a ring, use the suffix carbaldehyde.
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[Question] Naming Ketones [Answer]
Replace the terminal -e of the alkane name with –one Parent chain is the longest one that contains the ketone group Numbering begins at the end nearer the carbonyl carbon
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[Question] ketones and aldehydes as substituents [Answer]
The R–C=O as a substituent is an acyl group, used with the suffix -yl from the root of the carboxylic acid CH3 CO: acetyl; CHO: formyl; C6 H5 CO: benzoyl
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