Organic Chemistry, Loose-leaf Version
Organic Chemistry, Loose-leaf Version
8th Edition
ISBN: 9781305865549
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
Question
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Chapter 19, Problem 19.18P

(a)

Interpretation Introduction

Interpretation:

The product of the aldol reaction of the given compound and the α,β-unsaturated aldehyde or ketone formed from dehydration of the aldol product has to be drawn.

Concept introduction:

Aldol reaction is an addition reaction of aldehydes and ketones. Aldol reaction is a reversible reaction and occurs in the presence of a strong base like sodium hydroxide. One molecule (aldehyde or ketone) acts a nucleophile and attacks the electrophilic carbon center of the other molecule to give the addition product. The product is named β-hydroxy aldehyde if two aldehydes combine and β-hydroxy ketone if two ketones combine.

(a)

Expert Solution
Check Mark

Explanation of Solution

The aldol reaction product for the given compound has to be drawn.

The aldol reaction yield a β-hydroxy aldehyde as the product and on dehydration, water is eliminated and the product is formed.

Base abstracts a proton from the α carbon atom of aldehyde. Enolate anion is formed after abstraction of α proton from aldehyde molecule. Enolate ion attacks on the carbonyl carbon of the other molecule of aldehyde. The species formed in this step abstracts proton from water to give the β-hydroxy aldehyde. Loss of water molecule from the aldol product produces the product given below.

Organic Chemistry, Loose-leaf Version, Chapter 19, Problem 19.18P , additional homework tip  1

(b)

Interpretation Introduction

Interpretation:

The product of the aldol reaction of the given compound and the α,β-unsaturated aldehyde or ketone formed from dehydration of the aldol product has to be drawn.

Concept introduction:

Aldol reaction is an addition reaction of aldehydes and ketones. Aldol reaction is a reversible reaction and occurs in the presence of a strong base like sodium hydroxide. One molecule (aldehyde or ketone) acts a nucleophile and attacks the electrophilic carbon center of the other molecule to give the addition product. The product is named β-hydroxy aldehyde if two aldehydes combine and β-hydroxy ketone if two ketones combine.

(b)

Expert Solution
Check Mark

Explanation of Solution

The aldol reaction product for the given compound has to be drawn.

The aldol reaction yield a β-hydroxy ketone as the product and on dehydration, water is eliminated and the product is formed.

Base abstracts a proton from the α carbon atom of ketone. Enolate anion is formed after abstraction of α proton from ketone molecule. Enolate ion attacks on the carbonyl carbon of the other molecule of ketone. The species formed in this step abstracts proton from water to give the β-hydroxy ketone. Loss of water molecule from the aldol product produces the product given below.

Organic Chemistry, Loose-leaf Version, Chapter 19, Problem 19.18P , additional homework tip  2

(c)

Interpretation Introduction

Interpretation:

The product of the aldol reaction of the given compound and the α,β-unsaturated aldehyde or ketone formed from dehydration of the aldol product has to be drawn.

Concept introduction:

Aldol reaction is an addition reaction of aldehydes and ketones. Aldol reaction is a reversible reaction and occurs in the presence of a strong base like sodium hydroxide. One molecule (aldehyde or ketone) acts a nucleophile and attacks the electrophilic carbon center of the other molecule to give the addition product. The product is named β-hydroxy aldehyde if two aldehydes combine and β-hydroxy ketone if two ketones combine.

(c)

Expert Solution
Check Mark

Explanation of Solution

The aldol reaction product for the given compound has to be drawn.

The aldol reaction yield a β-hydroxy ketone as the product and on dehydration, water is eliminated and the product is formed.

Base abstracts a proton from the α carbon atom of the ketone. Enolate anion is formed after abstraction of α proton from ketone molecule. Enolate ion attacks on the carbonyl carbon of the same molecule. The species formed in above step abstracts proton from water to give the β-hydroxy ketone. Loss of water molecule from the aldol product produces the product given below.

Organic Chemistry, Loose-leaf Version, Chapter 19, Problem 19.18P , additional homework tip  3

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Chapter 19 Solutions

Organic Chemistry, Loose-leaf Version

Ch. 19.6 - Prob. 19.11PCh. 19.7 - Prob. 19.12PCh. 19.8 - Prob. 19.13PCh. 19.8 - Prob. 19.14PCh. 19.8 - Prob. 19.15PCh. 19.8 - Prob. 19.16PCh. 19.9 - Prob. 19.17PCh. 19.9 - Prob. AQCh. 19.9 - Prob. BQCh. 19.9 - Prob. CQCh. 19.9 - Prob. DQCh. 19.9 - Prob. EQCh. 19.9 - Prob. FQCh. 19.9 - Prob. GQCh. 19.9 - Intermediate G in Synthesis III is produced as a...Ch. 19.9 - Prob. IQCh. 19.9 - Prob. JQCh. 19 - Prob. 19.18PCh. 19 - Prob. 19.19PCh. 19 - Prob. 19.20PCh. 19 - Prob. 19.21PCh. 19 - Prob. 19.22PCh. 19 - Prob. 19.23PCh. 19 - Cyclohexene can be converted to...Ch. 19 - Prob. 19.25PCh. 19 - Prob. 19.26PCh. 19 - Prob. 19.27PCh. 19 - Prob. 19.28PCh. 19 - Prob. 19.29PCh. 19 - Prob. 19.30PCh. 19 - Draw structural formulas for the -ketoesters...Ch. 19 - Prob. 19.32PCh. 19 - Prob. 19.33PCh. 19 - Propose a synthesis for each ketone, using as one...Ch. 19 - Prob. 19.35PCh. 19 - Claisen condensation between diethyl phthalate and...Ch. 19 - Prob. 19.37PCh. 19 - Prob. 19.38PCh. 19 - Prob. 19.39PCh. 19 - Enamines normally react with methyl iodide to give...Ch. 19 - Prob. 19.41PCh. 19 - Prob. 19.42PCh. 19 - Prob. 19.43PCh. 19 - Prob. 19.44PCh. 19 - Prob. 19.45PCh. 19 - Prob. 19.46PCh. 19 - Prob. 19.47PCh. 19 - Prob. 19.48PCh. 19 - Prob. 19.49PCh. 19 - Prob. 19.50PCh. 19 - Prob. 19.51PCh. 19 - Prob. 19.52PCh. 19 - Show experimental conditions by which to carry out...Ch. 19 - Prob. 19.55PCh. 19 - The compound 3,5,5-trimethyl-2-cyclohexenone can...Ch. 19 - Prob. 19.57PCh. 19 - Prob. 19.58PCh. 19 - The widely used anticoagulant warfarin (see...Ch. 19 - Following is a retrosynthetic analysis for an...Ch. 19 - Following are the steps in one of the several...Ch. 19 - Prob. 19.62PCh. 19 - Prob. 19.63PCh. 19 - Prob. 19.65PCh. 19 - Prob. 19.67PCh. 19 - Prob. 19.68PCh. 19 - Prob. 19.69PCh. 19 - In Problem 7.28, we saw this two-step sequence in...Ch. 19 - Using your reaction roadmaps as a guide, show how...Ch. 19 - Using your reaction roadmaps as a guide, show how...Ch. 19 - Using your reaction roadmaps as a guide, show how...Ch. 19 - Using your reaction roadmaps as a guide, show how...Ch. 19 - Using your reaction roadmaps as a guide, show how...Ch. 19 - Prob. 19.79PCh. 19 - Prob. 19.80PCh. 19 - Prob. 19.81PCh. 19 - The following molecule undergoes an intramolecular...
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