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(a)
Interpretation:
The structure of enolate formed by the treatment of
Concept introduction:
In aldol condensation reaction, the base abstracts an acidic proton from the carbon atom to form enolate. This enolate or enol reacts with carbonyl compound that leads to the formation of hydroxyaldehyde or hydroxyketone which on further dehydration gives the conjugated enone.
(b)
Interpretation:
Whether the diastereomers of the product are formed in equal or in different amounts is to be stated.
Concept introduction:
Diastereomers are the type of stereoisomers that are non identical, non super imposable mirror images of each other. Diastereomers can have different physical and chemical properties. They must have two stereocentes.
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Chapter 22 Solutions
EBK ORGANIC CHEMISTRY
- Show how the following ketones might be synthesized from the indicated acids, usingany necessary reagents.(b) methyl cyclohexyl ketone from cyclohexanecarboxylic acidarrow_forwardFor the following structure, (a) propose the starting materials necessary to form it through an aldol reaction. (b) Identify the carbonyl electrophile, and the site of deprotonation for generation of the nucleophile to be used in the forward reaction. (Writing out the forward synthesis is not necessary.)arrow_forward(a) Account for the following :(i) CH3CHO is more reactive than CH3COCH3 towards reaction with HCN.(ii) Carboxylic acid is a stronger acid than phenol.(b) Write the chemical equations to illustrate the following name reactions:(i) Wolff-Kishner reduction (ii) Aldol condensation (iii) Cannizzaro reactionarrow_forward
- (a) p-Nitrobenzaldehyde is reactive toward nucleophilic additions than p- more methoxybenzaldehyde. Draw both of the molecular structures and explain the observation. (b) Cyclohexanone forms a cyanohydrin in good yield but 2,2,6-trimethylcyclohexanone does not. Draw both of the molecular structures and explain the observation.arrow_forwardThe following questions pertain to the esters shown and behavior under conditions of the Claisen condensation.(a) Two of these esters are converted to β-keto esters in good yield on treatment with sodium ethoxide and subsequent acidification of the reaction mixture. Which two are these? Write the structure of the Claisen condensation product of each one. (b) One ester is capable of being converted to a β-keto ester on treatment with sodium ethoxide, but the amount of β-keto ester that can be isolated after acidification of the reaction mixture is quite small. Which ester is this? (c) One ester is incapable of reaction under conditions of the Claisen condensation. Which one? Why?arrow_forward(b) Give both the structures and IUPAC names of the reactants for the compound below formed via a crossed aldol reaction with KOH as promotor. Explain why only one product is formed:arrow_forward
- Each of the following reactions has been carried out under conditions such that disubstitution or trisubstitution occurred. Identify the principal organic product in each case. (a) Nitration of p-chlorobenzoic acid (dinitration) (b) Bromination of aniline (tribromination) (c) Bromination of o-aminoacetophenone (dibromination) (d) Bromination of p-nitrophenol (dibromination) (e) Reaction of biphenyl with tert-butyl chloride and iron(III) chloride (dialkylation) (f) Sulfonation of phenol (disulfonation)arrow_forwardFrom the given structures which is(a) an acid halide? (b) a secondary amide (c) an aldehyde incapable of self-aldol consensation?arrow_forwardPredict the major products of the following base-catalyzed aldol condensations withdehydration.(a) benzophenone (PhCOPh) + propionaldehyde(b) 2,2@dimethylpropanal + acetophenonearrow_forward
- The ketone shown was prepared in a three-step sequence from ethyl trifluoroacetate. The first step in the sequence involved treating ethyl trifluoroacetate with ammonia to give compound A. Compound A was in turn converted to the desired ketone by way of compound B. Fill in the missing reagents in the sequence shown, and give the structures of compounds A and B.arrow_forward(a) Explain why an alkylamine is more basic than ammonia?(b) How would you convert(i) Aniline to nitrobenzene (ii) Aniline to iodobenzenearrow_forwardQuinapril (trade name Accupril) is used to treat high blood pressure and congestive heart failure. One step in the synthesis of quinapril involves reaction of the racemic alkyl bromide A with a single enantiomer of the amino ester B. (a) What two products are formed in this reaction? (b) Given the structure of quinapril, which one of these two products is needed tosynthesize the drug?arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
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