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793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] alpha hydrogen moves from alpha carbon to the carbonyl oxygen - RXN AT EQUILIBRIUM NOT RESONANCE (exist at RT) [Question]
|
tautomerization of ketone (keto-enol)
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] hemiacetals [Question]
|
aldehydes react with alcohols to form...
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] hemiketals [Question]
|
ketones react with alcohols to form...
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] catalyzed by acid or base where ROH acts as nucleophile and aldehyde undergos addition and can exist in equilibrium with ROH but too unstable to isolate [Question]
|
hemiacetal formation
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] second molar equivalent of ROH is added to the equilibrium of hemiacetal/hemiketal and R'OH in the presence of an acid to protonate OH group to produce good LG [Question]
|
acetals or ketals formed when...
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] acetals and ketals - they are unreactive toward bases so aldehydes/ketones temporarily changed to acetal/ketal to prevent it from reacting with a base - often create ring with HOCH2CH2OH (five membered ring) [Question]
|
blocking groups
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] they will establish equilbrium with their hydrate - geminal diol (two OH groups attached to previously carbonyl Carbon with its two substituents) [Question]
|
what happens when aldehydes/ketones dissolved in aqueous solution?
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] when aldehyde or ketone reacts with another aldehyde or ketone, catalyzed by acid or base [Question]
|
aldol condensation
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] 1. base abstracts alpha-H 2. enolate ion attacks carbonyl C 3. resulting alkoxide ion removes H+ from water and regenerates catalyst and leaves aldol product [Question]
|
base catalyzed aldol condensation
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] 1. acid catalyzed tautomerization to an enol 2. carbonyl O is protonated (making carbonyl highly electrophillic) 3. enol can attack electrophile [Question]
|
acid catalyzed aldol condensation
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] become and enal bc the aldol is unstable and the enal is stabilized by its conjugated double bonds [Question]
|
with heat and a base, an aldol will ____ because ____
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] presence of base or acid [Question]
|
when do halogens add to ketones at the alpha carbon?
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] halogenated carbonyl, halogen ion, and water - it is also difficult to prevent halogenation at more than one alpha position [Question]
|
in the presence of a base, halogenation of ketones at the alpha carbon results in..
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] halogenated carbonyl, halogen ion, and regenerated H+ acid [Question]
|
in the presence of the acid, halogenation of ketones at the alpha carbon results in...
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] base + methyl ketone results in alpha carbon completely halogenated -> where base then attacks carbonyl and triple halogenated alpha carbon becomes a leaving group when C=O regenerated -> result in carboxylate ion and haloform [Question]
|
haloform rxn
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] HCX3 [Question]
|
haloform definition
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] converts ketone to alkene using phosphorous ylide [Question]
|
Wittig rxn
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] neutral molecule that combines with negativly charged carbanion for use in the Wittig rxn - Phosphorous bound to 3 benzyl rings and a negatively charged carbon [Question]
|
ylide
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] negatively charged carbanion attacks carbonyl C of ketone/aldehyde forming betaine (nucleophillic addition) that quickly breaks down to an alkene with the R group on the ylide [Question]
|
steps in Wittig rxn
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] alpha beta unsaturated carbonyl [Question]
|
a carbonyl cmpd with a dbl bond between alpha and beta C can is called _____
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] 1. beta carbon less susceptible to nucleophillic attack due to e' withdrawing capability of carbonyl 2. provides resonance when carbocation formed when all e' are at the O of the carbonyl bond [Question]
|
characteristics of the C-C dbl bond in alpha beta unsaturated carbonyl
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] O || H-C-OH [Question]
|
formic acid
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] O || CH3-C-OH [Question]
|
acetic acid
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] O || benzene-C-OH [Question]
|
benzoic acid
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] acids or substrates in nucleophillic substitution reactions [Question]
|
carboxylic acids like to be have as ____ in ____ rxns
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] they are very strong for organic acids bc when dissociated, their conjugate base is stabilized by resonance [Question]
|
acidity of carboxylic acids...
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] e' withdrawing groups bc they help further stabilize conjugate base [Question]
|
what types of group on the alpha carbon will increase the acidity of a carboxylic acid?
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] high bp due to H bond dimers, if saturated and more than 8 carbons - solids, unsaturated impede crystal lattice structure and lower BP [Question]
|
physical properties of carboxylic acids
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] <4 C's: soluble 5-10 C's: increasingly less soluble >10 C's: insobluble [Question]
|
when can carboxylic acids mix with water?
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] yes, soluble bc dimer form allows carboxylic acid to solvate w/o disrupting hydrogen bonds of the dimer [Question]
|
carboxylic acids solubility in nonpolar solvents
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] process in where carboxylic acid loses CO2, rxn is usually exothermic but has high activation energy [Question]
|
decarboxylation
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] when the beta carbon is a carbonyl bc either the anion intermediate is sstabilized by resonance or the acid forms stable cyclic intermediate [Question]
|
how is the activation energy of decarboxylation lowered?
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] carboxylic acids and inorganic acid chlorides (SOCl2, PCl3, and PCl5) [Question]
|
what is needed to form acyl chlorides?
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] bronsted-lowry - they donate alpha hydrogen like aldehydes but the e' withdrawing Cl stabilizes conjugate base more than the H of an aldehyde [Question]
|
acyl chlorides act as what kind of acids?
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] most reactive bc of the stability of the Cl- leaving group [Question]
|
acyl chlorides are the most or least reactive of the carboxylic acid derivatives, and why?
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] it will hydrolyze to give the corresponding carboxylic acid, and can occur under acidic or basic conditions [Question]
|
what happens when any carboxylic acid derivative is in the presence of water?
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] ester [Question]
|
acid chloride + alcohol =
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] amide [Question]
|
acid chloride + amine =
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] anhydride [Question]
|
acid chloride + RCOOH =
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] esters (via nucleophilic substitution), catalyzed by strong acid [Question]
|
alcohols + carboxylic acids =
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] alcohols + carboxylic acids = esters [Question]
|
esterification
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] esters + alcohol = carboxylic acid way to trade alkoxy groups on an ester [Question]
|
transesterification
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] production of ketone from acetoacetic ester due to strongly acidic properties [Question]
|
acetoacetic ester synthesis
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] 1. base is added to remove alpha H's 2. alkyl halide alkylates the resulting enolate ion 3. alkylacetoacetic ester is decarboxylated in presence of acid and heat resulting in ketone [Question]
|
steps in acetoacetic ester synthesis
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] amine + carboxylic acids or one of its derivities [Question]
|
amides are formed when...
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] acyl chloride > acid anhydride > carboxylic acid > ester > amide [Question]
|
order of reactivity of carboxylic acid (most to least)
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] 1. they may act as Lewis base donating their lone pair of e's 2. they may act as a nucleophile where lone pair of e's attacks positive charge 3. N can take on 4th bond and become positively charged [Question]
|
important facts about nitrogen containing cmpds
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] e' withdrawing substituents, steric hindrence, aromaticity [Question]
|
what decreases amine basicity
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] e' donating substituents [Question]
|
what increases amine basicity
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] 2 > 1 > ammonia [Question]
|
amine basicity from highest to lowest when functional groups are e' donating?
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] hydrogen bond capability of ammonia to 2 amines raise bp and increases solubility in water [Question]
|
physical properties of ammonia and amines
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] at RT, the lone pair of e's moves rapidly and inverts configuration rapidly so molecule spends equal amt of time in each enantiomer [Question]
|
what is special about chiral amines?
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] imines/enamines + water (requires acid catalyst) [Question]
|
aldehydes/ketones + amines =
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] 1. lone pair on amine attacks ketone or aldehyde in nucleophilic addition 2. OH grp is protonated by acid catalyst to make a good leaving group 3. unstable intermediate will produce enamine or imine [Question]
|
steps in condensation rxn with ketones
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] secondary amine gives up its alpha hydrogen in condensation rxn with ketones where alkene with amine grp (enamine) forms [Question]
|
enamine formed when...
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] hydrogen lost from primary amine to make a C=N when water leaves unstable intermediate in condesnation rxn with ketones [Question]
|
imine formed when...
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] exist as a tautomer with its corresponding enamine [Question]
|
imine products of condensation rxns can..
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] reduces ketone/aldehyde by removing oxygen and replaces it with 2 hydrogens - used for when molecule can't survive hot acid to reduce to alkane [Question]
|
Wolff-Kishner rxn
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] 1. lone pair of hydrazine N attacks ketone (Nu: addition) 2. acid protonates OH grp to make good LG 3. C=N formed to release water forming hydrazone and acid 4. hot strong acid added to deprotonate N of C=N to produce alkane, water, and N2 gas [Question]
|
steps in wolff-kishner reduction
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] alkylated with alkyl halides in a nuclephilic substitution rxn [Question]
|
amines can be alkylated with ___ in a _______ rxn
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] poor - they need to be converted to quarternary ammonium salt by repeated alkylations to be a good leaving group [Question]
|
amino groups are good or poor leaving groups?
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] E2 mechanism with strong base [Question]
|
what is the rxn mechanism to eliminate a quarternary ammonium salt?
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] heating quarternary ammonium hydroxide and results in alkene [Question]
|
Hoffman elimination
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] least stable alkene in the Hoffman elimination [Question]
|
Hoffman product
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] most stable alkene in the Hoffman elimination [Question]
|
Saytzeff product
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] HO-N=O + H+ --> [:N+=O:: <-> :N+-O:+] + H2O (product is nitrosonium ion) [Question]
|
nitrous acid + strong acid =
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] diazonium salt [Question]
|
primary amines + nitrous acid =
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] two Nitrogens triple bonded to each other as a functional group [Question]
|
diazoniam group
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] 1. nitrous acid protonated by strong acid 2. resulting nitrosonium ion reacts with primary amine 3. resulting N-nitrosonium (unstable) deprotonates to N-nitrosoamine and tautomerizes to diazenol 4. diazenol in acid dehydrates to diazonium ion [Question]
|
diazotization of an amine rxn steps
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] R-N=N-O-H (tautomer of RHN-N=O) [Question]
|
diazenol
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] aromatic primary amines [Question]
|
diazotization of an amine requires...
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] OH group, halide, H, or -N=N-Ar [Question]
|
the diazonium grp can be replaced to the following..
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] N-nitrosoamine (amine N's lone pair still attacks positive charge on the nitrosonium ion and then water abstracts proton to form N-nitrosoamine) [Question]
|
secondary amines + nitrosonium ion =
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] caboxylic derivative containing nitrogen [Question]
|
amide
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] weak acid or weak base [Question]
|
amides behave as...
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] strong acids or strong bases [Question]
|
amides are hydrolyzed by...
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] hydrogen bond with each other [Question]
|
amides with a hydrogen attached are able to...
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] cyclic amides, highly reactive due to large ring strain [Question]
|
beta lactams
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] primary amides react with stronly basic solns of Cl or Br to form primary amines with CO2 as the byproduct [Question]
|
Hoffman degradation
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] base abstracts H from 1-amide>(-)N attacks X2 >base abstracts H from resulting N-haloamide>rearrangment moves R grp to N (Br as LG) >OH- attacks C in isocyonate while lone pair abstracts H from H2O>resulting carbamic acid decarboxylated>>primary amine [Question]
|
steps in Hoffman degradation
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] R-N=C=O, rearrangement that occurs in product of deprotnated product of N-haloamide and base (intermediate in Hoffman degradation rxn) [Question]
|
isocyonate
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] R-NH-COOH, formed when isocyanate reacts with water [Question]
|
carbamic acid
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] other rxns rely on SN2 reaction which prevents production of amines on a tertiary carbon -- Hoffman degradation can produce amines w/ primary, secondary, or tertiary alkyl position [Question]
|
advantage of Hoffman degradation over other methods of producing amines?
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] O || OH-P-OH | OH [Question]
|
phosphoric acid
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] phosphoric anhydrides [Question]
|
when heated, phosphoric acid forms...
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
793f00e5_Flashcards_about_EK_Orgo_3__Question
|
[Answer] esters [Question]
|
phosphoric anhydrides + alcohols =
|
[] |
Flashcards about EK Orgo 3
|
Question
|
http://www.studystack.com/flashcard-529146
|
22/1438043062635.98_20150728002422-00059-ip-10-236-191-2_717672241_3.json
|
41571226_ards_about_Introduction_Baking__Answer
|
[Question] Blend of half “soft” (low protein) and half hard (high protein) wheat -most common type of flour [Answer]
|
All purpose flour
|
[] |
Flashcards about Introduction Baking
|
Answer
|
http://www.studystack.com/flashcard-270606
|
22/1438042990177.43_20150728002310-00274-ip-10-236-191-2_738375923_3.json
|
41571226_ards_about_Introduction_Baking__Answer
|
[Question] Thick sweet syrup made from cornstarch [Answer]
|
corn syrup
|
[] |
Flashcards about Introduction Baking
|
Answer
|
http://www.studystack.com/flashcard-270606
|
22/1438042990177.43_20150728002310-00274-ip-10-236-191-2_738375923_3.json
|
41571226_ards_about_Introduction_Baking__Answer
|
[Question] Increases the volume of a dough or by adding air or other gas [Answer]
|
Leavener
|
[] |
Flashcards about Introduction Baking
|
Answer
|
http://www.studystack.com/flashcard-270606
|
22/1438042990177.43_20150728002310-00274-ip-10-236-191-2_738375923_3.json
|
41571226_ards_about_Introduction_Baking__Answer
|
[Question] Steel blade used to cut dough or used to cut soft ingredients such as butter [Answer]
|
Bench scraper
|
[] |
Flashcards about Introduction Baking
|
Answer
|
http://www.studystack.com/flashcard-270606
|
22/1438042990177.43_20150728002310-00274-ip-10-236-191-2_738375923_3.json
|
41571226_ards_about_Introduction_Baking__Answer
|
[Question] Harder or stronger than all purpose flour because if has more protein in it. [Answer]
|
Bread flour
|
[] |
Flashcards about Introduction Baking
|
Answer
|
http://www.studystack.com/flashcard-270606
|
22/1438042990177.43_20150728002310-00274-ip-10-236-191-2_738375923_3.json
|
41571226_ards_about_Introduction_Baking__Answer
|
[Question] A mixture of egg and water or milk; brushed on top of breads and pastries to give a glossy sheen [Answer]
|
Egg wash
|
[] |
Flashcards about Introduction Baking
|
Answer
|
http://www.studystack.com/flashcard-270606
|
22/1438042990177.43_20150728002310-00274-ip-10-236-191-2_738375923_3.json
|
41571226_ards_about_Introduction_Baking__Answer
|
[Question] Used to create a decorative edge on iced cakes [Answer]
|
Cake comb
|
[] |
Flashcards about Introduction Baking
|
Answer
|
http://www.studystack.com/flashcard-270606
|
22/1438042990177.43_20150728002310-00274-ip-10-236-191-2_738375923_3.json
|
41571226_ards_about_Introduction_Baking__Answer
|
[Question] Baking powder [Answer]
|
Chemical leavener
|
[] |
Flashcards about Introduction Baking
|
Answer
|
http://www.studystack.com/flashcard-270606
|
22/1438042990177.43_20150728002310-00274-ip-10-236-191-2_738375923_3.json
|
41571226_ards_about_Introduction_Baking__Answer
|
[Question] work dough by hand [Answer]
|
Knead
|
[] |
Flashcards about Introduction Baking
|
Answer
|
http://www.studystack.com/flashcard-270606
|
22/1438042990177.43_20150728002310-00274-ip-10-236-191-2_738375923_3.json
|
41571226_ards_about_Introduction_Baking__Answer
|
[Question] Yeast, a tiny single celled organism [Answer]
|
Organic leavener
|
[] |
Flashcards about Introduction Baking
|
Answer
|
http://www.studystack.com/flashcard-270606
|
22/1438042990177.43_20150728002310-00274-ip-10-236-191-2_738375923_3.json
|
41571226_ards_about_Introduction_Baking__Answer
|
[Question] Box that holds dough as it rises; thermostats to control heat and steam [Answer]
|
Proofer
|
[] |
Flashcards about Introduction Baking
|
Answer
|
http://www.studystack.com/flashcard-270606
|
22/1438042990177.43_20150728002310-00274-ip-10-236-191-2_738375923_3.json
|
41571226_ards_about_Introduction_Baking__Answer
|
[Question] Made from Cassava Root, a starchy tropical tuber; used to thicken fruit pie and to make pudding [Answer]
|
Tapioca
|
[] |
Flashcards about Introduction Baking
|
Answer
|
http://www.studystack.com/flashcard-270606
|
22/1438042990177.43_20150728002310-00274-ip-10-236-191-2_738375923_3.json
|
41571226_ards_about_Introduction_Baking__Answer
|
[Question] Steam and air [Answer]
|
Pysical leavener
|
[] |
Flashcards about Introduction Baking
|
Answer
|
http://www.studystack.com/flashcard-270606
|
22/1438042990177.43_20150728002310-00274-ip-10-236-191-2_738375923_3.json
|
41571226_ards_about_Introduction_Baking__Answer
|
[Question] Sugar ground into fine easily dissovible powder [Answer]
|
Confectionary sugar
|
[] |
Flashcards about Introduction Baking
|
Answer
|
http://www.studystack.com/flashcard-270606
|
22/1438042990177.43_20150728002310-00274-ip-10-236-191-2_738375923_3.json
|
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