Organic Chemistry
Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
Question
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Chapter 17.19, Problem 52P

(a)

Interpretation Introduction

Interpretation:

A major product in the given reaction should be found.

Concept Introduction:

The resonance gives for α,β- unsaturated carbonyl compound which shoes that the compound has two electrophilic positions are β- carbon and carbonyl carbon.  That is a nucleophile can be add either to β- carbon or carbonyl carbon.  Conjugate addition and direct addition are depending upon the nature of the nucleophile.

Nucleophilic addition to the β- carbon (conjugate addition) is irreversible.

Nucleophilic addition to the carbonyl carbon (direct addition) is irreversible or reversible.  When nucleophile is weak base such as alcohol, an amine or thiol, then direct addition is reversible, because of weak base is worthy leaving group.

(b)

Interpretation Introduction

Interpretation:

A major product in the given reaction should be found.

Concept Introduction:

The resonance gives for α,β- unsaturated carbonyl compound which shoes that the compound has two electrophilic positions are β- carbon and carbonyl carbon.  That is a nucleophile can be add either to β- carbon or carbonyl carbon.  Conjugate addition and direct addition are depending upon the nature of the nucleophile.

Nucleophilic addition to the β- carbon (conjugate addition) is irreversible.

Nucleophilic addition to the carbonyl carbon (direct addition) is irreversible or reversible.  When nucleophile is weak base such as alcohol, an amine or thiol, then direct addition is reversible, because of weak base is worthy leaving group.

(c)

Interpretation Introduction

Interpretation:

A major product in the given reaction should be found.

Concept Introduction:

The resonance gives for α,β- unsaturated carbonyl compound which shoes that the compound has two electrophilic positions are β- carbon and carbonyl carbon.  That is a nucleophile can be add either to β- carbon or carbonyl carbon.  Conjugate addition and direct addition are depending upon the nature of the nucleophile.

Nucleophilic addition to the β- carbon (conjugate addition) is irreversible.

Nucleophilic addition to the carbonyl carbon (direct addition) is irreversible or reversible.  When nucleophile is weak base such as alcohol, an amine or thiol, then direct addition is reversible, because of weak base is worthy leaving group.

(d)

Interpretation Introduction

Interpretation:

A major product in the given reaction should be found.

Concept Introduction:

The resonance gives for α,β- unsaturated carbonyl compound which shoes that the compound has two electrophilic positions are β- carbon and carbonyl carbon.  That is a nucleophile can be add either to β- carbon or carbonyl carbon.  Conjugate addition and direct addition are depending upon the nature of the nucleophile.

Nucleophilic addition to the β- carbon (conjugate addition) is irreversible.

Nucleophilic addition to the carbonyl carbon (direct addition) is irreversible or reversible.  When nucleophile is weak base such as alcohol, an amine or thiol, then direct addition is reversible, because of weak base is worthy leaving group.

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Chapter 17 Solutions

Organic Chemistry

Ch. 17.4 - Show how the following compounds can be...Ch. 17.5 - Prob. 13PCh. 17.5 - Prob. 14PCh. 17.6 - In the mechanism for cyanohydrin formation, why is...Ch. 17.6 - Prob. 16PCh. 17.6 - Prob. 17PCh. 17.6 - Show two ways to convert an alkyl halide into a...Ch. 17.7 - Prob. 20PCh. 17.7 - Prob. 21PCh. 17.7 - Prob. 22PCh. 17.7 - Prob. 23PCh. 17.8 - Prob. 24PCh. 17.9 - What reducing agents should be used to obtain the...Ch. 17.9 - Prob. 26PCh. 17.9 - Prob. 27PCh. 17.10 - Prob. 28PCh. 17.10 - Prob. 29PCh. 17.10 - Prob. 30PCh. 17.10 - The pKa of protonated acetone is about 7.5. and...Ch. 17.10 - Prob. 32PCh. 17.10 - Prob. 33PCh. 17.10 - Prob. 34PCh. 17.10 - Excess ammonia must be used when a primary amine...Ch. 17.10 - The compounds commonly known as amino acids are...Ch. 17.11 - Hydration of an aldehyde is also catalyzed by...Ch. 17.11 - Which ketone forms the most hydrate in an aqueous...Ch. 17.11 - When trichloroacetaldehyde is dissolved in water,...Ch. 17.12 - Which of the following are a. hermiacetals? b....Ch. 17.12 - Prob. 41PCh. 17.12 - Explain why an acetal can be isolated but most...Ch. 17.13 - Prob. 43PCh. 17.13 - Prob. 44PCh. 17.13 - What products would be formed from the proceedings...Ch. 17.13 - a. In a six-step synthesis, what is the yield of...Ch. 17.13 - Show how each of the following compounds could be...Ch. 17.15 - Prob. 48PCh. 17.17 - Prob. 50PCh. 17.18 - Prob. 51PCh. 17.19 - Prob. 52PCh. 17 - Draw the structure for each of the following: a....Ch. 17 - Prob. 54PCh. 17 - Prob. 55PCh. 17 - a. Show the reagents required to form the primary...Ch. 17 - Prob. 57PCh. 17 - Using cyclohexanone as the starting material,...Ch. 17 - Prob. 59PCh. 17 - 60. Show how each of the following compounds could...Ch. 17 - Fill in the boxes:Ch. 17 - Prob. 62PCh. 17 - Identify A through O:Ch. 17 - Prob. 64PCh. 17 - Prob. 65PCh. 17 - Prob. 66PCh. 17 - How many signals would the product of the...Ch. 17 - Prob. 68PCh. 17 - Prob. 69PCh. 17 - Prob. 70PCh. 17 - Prob. 71PCh. 17 - Prob. 72PCh. 17 - Prob. 73PCh. 17 - Prob. 74PCh. 17 - Prob. 75PCh. 17 - Prob. 76PCh. 17 - Prob. 77PCh. 17 - A compound gives the following IR spectrum. Upon...Ch. 17 - a. Propose a mechanism for the following reaction:...Ch. 17 - Prob. 80PCh. 17 - Prob. 81PCh. 17 - Prob. 82PCh. 17 - Prob. 83PCh. 17 - Prob. 84PCh. 17 - In the presence of an acid catalyst, acetaldehyde...Ch. 17 - Prob. 86PCh. 17 - Prob. 87PCh. 17 - Prob. 88PCh. 17 - A compound reacts with methylmagnesium bromide...Ch. 17 - Show how each of the following compounds can be...Ch. 17 - Prob. 91PCh. 17 - Prob. 92PCh. 17 - The pKa values of the carboxylic acid groups of...Ch. 17 - The Baylis-Hillman reaction is a DABCO...Ch. 17 - Prob. 95PCh. 17 - Prob. 96P
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