Organic Chemistry
Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Chapter 17, Problem 54P

(a)

Interpretation Introduction

Interpretation:

The products for the given reaction should be identified.

Concept Introduction:

Nucleophilic acyl substitution:

The carbonyl group of a carboxylic acid or carboxylic acid derivative can be replaced with another group. Therefore, aldehyde and ketone undergoes nucleophilic acyl substitution reactions.

Organic Chemistry, Chapter 17, Problem 54P , additional homework tip  1

(b)

Interpretation Introduction

Interpretation:

The products for the given reaction should be identified.

Concept Introduction:

Reaction for aldehydes and ketones in presence of primary amine is as follows,

The carbonyl group of a carboxylic acid or carboxylic acid derivative gets converted into imine in presence of primary amine which is depicted as follows,

Organic Chemistry, Chapter 17, Problem 54P , additional homework tip  2

(c)

Interpretation Introduction

Interpretation:

The products for the given reaction should be identified.

Concept Introduction:

The ketone which is carboxylic acid derivative in presence of NaBH4andH3O+ tend to give secondary alcohol and the general reaction is as follows,

Organic Chemistry, Chapter 17, Problem 54P , additional homework tip  3

(d)

Interpretation Introduction

Interpretation:

The product for the given reaction should be identified.

Concept Introduction:

The carbonyl group of a carboxylic acid or carboxylic acid derivative is attached to a group that can be replaced with another group.  Therefore, aldehyde and ketone undergoes nucleophilic acyl substitution reactions.

Generally reduction of aldehyde gives primary alcohol and reduction of ketone gives secondary alcohol.

Organic Chemistry, Chapter 17, Problem 54P , additional homework tip  4

(e)

Interpretation Introduction

Interpretation:

The product for the given reaction should be identified.

Concept Introduction:

Nucleophilic acyl substitution:

The carbonyl group of a carboxylic acid or carboxylic acid derivative is attached to a group that can be replaced with another group. Therefore, aldehyde and ketone undergoes nucleophilic acyl substitution reactions.

Generally reduction of aldehyde gives primary alcohol and reduction of ketone gives secondary alcohol.

Organic Chemistry, Chapter 17, Problem 54P , additional homework tip  5

(f)

Interpretation Introduction

Interpretation:

The product for the given reaction should be identified.

Concept Introduction:

Nucleophilic acyl substitution:

The carbonyl group of a carboxylic acid or carboxylic acid derivative is attached to a group that can be replaced with another group.  Therefore, aldehyde and ketone undergoes nucleophilic acyl substitution reactions.

Organic Chemistry, Chapter 17, Problem 54P , additional homework tip  6

The carboxylic acid derivatives namely aldehyde and ketones generally gets protected from converted to acetals in presence of diols.

(g)

Interpretation Introduction

Interpretation:

The product for the given reaction should be identified.

Concept Introduction:

Nucleophilic acyl substitution:

The carbonyl group of a carboxylic acid or carboxylic acid derivative is attached to a group that can be replaced with another group. Therefore, aldehyde and ketone undergoes nucleophilic acyl substitution reactions.

Organic Chemistry, Chapter 17, Problem 54P , additional homework tip  7

Blurred answer

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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