Organic Chemistry (9th Edition)
Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
Question
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Chapter 22.4, Problem 22.8P

(a)

Interpretation Introduction

Interpretation:

The expected products of the given acid catalysed reaction are to be stated.

Concept introduction:

When aldehydes or ketones react with a primary amine, formation of a carbinolamine takes place. Then, dehydration takes place to give C=N double bond of an imine. Imine formation takes place in the presence of an acid or a base. This reaction is reversible and it is accompanied by loss of water molecule.

(b)

Interpretation Introduction

Interpretation:

The expected products of the given acid catalysed reaction are to be stated.

Concept introduction:

When aldehydes or ketones react with a secondary amine, formation of enamine takes place. The nitrogen analog of an enol is known as enamine. From the resonating structures of enamine, it is clear that it nucleophilic in nature.

(c)

Interpretation Introduction

Interpretation:

The expected products of the given acid catalysed reaction are to be stated.

Concept introduction:

When aldehydes or ketones react with a primary amine, formation of a carbinolamine takes place. Then, dehydration takes place to give C=N double bond of an imine. Imine formation takes place in the presence of an acid or a base. This reaction is reversible and it is accompanied by loss of water molecule.

(d)

Interpretation Introduction

Interpretation:

The expected products of the given acid catalysed reaction are to be stated.

Concept introduction:

When aldehydes or ketones react with a secondary amine, formation of enamine takes place. The nitrogen analog of an enol is known as enamine. From the resonating structures of enamine, it is clear that it nucleophilic in nature.

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(a) How will you obtain the following :(i) Benzaldehyde from Phenol             (ii) Benzoic acid from Aniline(b) Give reasons :(i) Aldehydes are more reactive than ketones towards nucleophilic reagents.(ii) Electrophilic substitution in benzoic acid takes place at meta position.(iii) Carboxylic acids do not give the characteristic reactions of carbonyl group.
(a) Illustrate the following name reactions :(i) Hell-Volhard-Zelinsky reaction        (ii) Wolff-Kishner reduction reaction(b) How are the following conversions carried out:(i) Ethylcyanide to ethanoic acid         (ii) Butan-l-ol to butanoic acid(iii) Methylbenzene to benzoic acidWrite chemical equations for the involved reactions.
(a) Illustrate the following name reactions giving suitable example in each case :(i) Clemmensen reduction                     (ii) Hell-Volhard-Zelinsky reaction(b) How are the following conversions carried out?(i) Ethylcyanide to ethanoic acid          (ii) Butan-l-ol to butanoic acid(iii) Benzoic acid to m-bromobenzoic acid

Chapter 22 Solutions

Organic Chemistry (9th Edition)

Ch. 22.5C - Acid-catalyzed halogenation is synthetically...Ch. 22.6 - Show the products of the reactions of these...Ch. 22.7A - Prob. 22.18PCh. 22.7A - Prob. 22.19PCh. 22.7A - Prob. 22.20PCh. 22.7B - Prob. 22.21PCh. 22.8 - Prob. 22.22PCh. 22.8 - Prob. 22.24PCh. 22.9 - Prob. 22.25PCh. 22.9 - Prob. 22.26PCh. 22.9 - Prob. 22.27PCh. 22.9 - Prob. 22.28PCh. 22.9 - Prob. 22.29PCh. 22.10 - When cyclodecane-1,6-dione is treated with sodium...Ch. 22.11 - Prob. 22.32PCh. 22.11 - Prob. 22.33PCh. 22.12 - Prob. 22.34PCh. 22.12 - Prob. 22.35PCh. 22.12 - Prob. 22.36PCh. 22.12 - Prob. 22.37PCh. 22.12 - Show what esters would undergo Claisen...Ch. 22.13 - Prob. 22.39PCh. 22.13 - Prob. 22.40PCh. 22.14 - Prob. 22.41PCh. 22.14 - Prob. 22.42PCh. 22.14 - Show how crossed Claisen condensations could be...Ch. 22.14 - Prob. 22.44PCh. 22.14 - Prob. 22.45PCh. 22.15 - Prob. 22.46PCh. 22.16 - Prob. 22.47PCh. 22.16 - Prob. 22.48PCh. 22.17 - Prob. 22.49PCh. 22.17 - Prob. 22.50PCh. 22.17 - Prob. 22.51PCh. 22.18 - Prob. 22.52PCh. 22.18 - Prob. 22.53PCh. 22.18 - Prob. 22.54PCh. 22.18 - Prob. 22.55PCh. 22.18 - Prob. 22.56PCh. 22.19 - Prob. 22.57PCh. 22.19 - Prob. 22.58PCh. 22.19 - Prob. 22.59PCh. 22 - Prob. 22.60SPCh. 22 - 1. Rank the following compounds in order of...Ch. 22 - Prob. 22.62SPCh. 22 - Prob. 22.63SPCh. 22 - Prob. 22.64SPCh. 22 - Pentane-2,4-dione (acetylacetone) exists as a...Ch. 22 - a. Rank these compounds in order of increasing...Ch. 22 - Prob. 22.67SPCh. 22 - Prob. 22.68SPCh. 22 - 22-69 Predict the products of the following...Ch. 22 - Predict the products of these reaction sequences.Ch. 22 - Show how you would accomplish the following...Ch. 22 - Prob. 22.72SPCh. 22 - Prob. 22.73SPCh. 22 - Prob. 22.74SPCh. 22 - The Knoevenagel condensation is a special case of...Ch. 22 - Prob. 22.76SPCh. 22 - Propose mechanisms for the following reactions.Ch. 22 - Prob. 22.78SPCh. 22 - Show how you would accomplish the following...Ch. 22 - Prob. 22.80SPCh. 22 - Propose a mechanism for the following reaction....Ch. 22 - Prob. 22.83SPCh. 22 - Prob. 22.84SPCh. 22 - Prob. 22.85SP
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