Organic Chemistry, Binder Ready Version
Organic Chemistry, Binder Ready Version
2nd Edition
ISBN: 9781118454312
Author: David R. Klein
Publisher: WILEY
Question
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Chapter 23.9, Problem 25PTS

(a)

Interpretation Introduction

Interpretation: The major products are to be found when the given compounds are treated with excess methyl iodide followed by aqueous silver oxide and heat.

Concept Introduction:

The reagents such as methyl iodide and silver oxide are used as the reaction conditions which are called Hofmann elimination. The amines undergo exhaustive alkylation in the presence of excess methyl iodide producing quaternaryammonium salt which is excellent leaving group. After treatment with strong base, aqueous silver oxide and heat, the quaternary ammonium salt provides alkenes. Alkene formation involves in E2 elimination.  Through E2 elimination, the major product is less substituted alkene with trace amount of more substituted alkene.

Organic Chemistry, Binder Ready Version, Chapter 23.9, Problem 25PTS , additional homework tip  1

To find: The major product of cyclohexyl amine in Hofmann elimination

Draw and analyze the structure of cyclohexyl amine

Organic Chemistry, Binder Ready Version, Chapter 23.9, Problem 25PTS , additional homework tip  2

(b)

Interpretation Introduction

Interpretation: The major products are to be found when the given compounds are treated with excess methyl iodide followed by aqueous silver oxide and heat.

Concept Introduction:

The reagents such as methyl iodide and silver oxide are used as the reaction conditions which are called Hofmann elimination. The amines undergo exhaustive alkylation in the presence of excess methyl iodide producing quaternaryammonium salt which is excellent leaving group. After treatment with strong base, aqueous silver oxide and heat, the quaternary ammonium salt provides alkenes. Alkene formation involves in E2 elimination.  Through E2 elimination, the major product is less substituted alkene with trace amount of more substituted alkene.

Organic Chemistry, Binder Ready Version, Chapter 23.9, Problem 25PTS , additional homework tip  3

To find: The major product of (R)-3-methyl-2-butanamine in Hofmann elimination

Draw and analyze the structure of (R)-3-methyl-2-butanamine

Organic Chemistry, Binder Ready Version, Chapter 23.9, Problem 25PTS , additional homework tip  4

(c)

Interpretation Introduction

Interpretation: The major products are to be found when the given compounds are treated with excess methyl iodide followed by aqueous silver oxide and heat.

Concept Introduction:

The reagents such as methyl iodide and silver oxide are used as the reaction conditions which are called Hofmann elimination. The amines undergo exhaustive alkylation in the presence of excess methyl iodide producing quaternaryammonium salt which is excellent leaving group. After treatment with strong base, aqueous silver oxide and heat, the quaternary ammonium salt provides alkenes. Alkene formation involves in E2 elimination.  Through E2 elimination, the major product is less substituted alkene with trace amount of more substituted alkene.

Organic Chemistry, Binder Ready Version, Chapter 23.9, Problem 25PTS , additional homework tip  5

To find: The major product of N,N-dimethyl-1-phenylpropan-2-amine in Hofmann elimination

Draw and analyze the structure of N,N-dimethyl-1-phenylpropan-2-amine.

Organic Chemistry, Binder Ready Version, Chapter 23.9, Problem 25PTS , additional homework tip  6

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Chapter 23 Solutions

Organic Chemistry, Binder Ready Version

Ch. 23.4 - Prob. 10CCCh. 23.4 - Prob. 11CCCh. 23.5 - Prob. 2LTSCh. 23.5 - Prob. 12PTSCh. 23.5 - Prob. 13PTSCh. 23.6 - Prob. 3LTSCh. 23.6 - Prob. 14PTSCh. 23.6 - Prob. 15ATSCh. 23.6 - Prob. 16ATSCh. 23.6 - Prob. 17ATSCh. 23.7 - Prob. 18PTSCh. 23.7 - Prob. 19PTSCh. 23.7 - Prob. 20PTSCh. 23.7 - Prob. 21ATSCh. 23.8 - Prob. 22CCCh. 23.8 - Prob. 23CCCh. 23.8 - Prob. 24CCCh. 23.9 - Prob. 5LTSCh. 23.9 - Prob. 25PTSCh. 23.9 - Prob. 26ATSCh. 23.9 - Prob. 27ATSCh. 23.9 - Prob. 28ATSCh. 23.10 - Prob. 29CCCh. 23.11 - Prob. 30CCCh. 23.11 - Prob. 6LTSCh. 23.11 - Prob. 31PTSCh. 23.11 - Prob. 32ATSCh. 23.11 - Prob. 33ATSCh. 23.12 - Prob. 34CCCh. 23.12 - Prob. 35CCCh. 23.13 - Prob. 36CCCh. 23.13 - Prob. 37CCCh. 23 - Prob. 38PPCh. 23 - Prob. 39PPCh. 23 - Prob. 40PPCh. 23 - Prob. 41PPCh. 23 - Prob. 42PPCh. 23 - Prob. 43PPCh. 23 - Prob. 44PPCh. 23 - Prob. 45PPCh. 23 - Prob. 46PPCh. 23 - Prob. 47PPCh. 23 - Prob. 48PPCh. 23 - Prob. 49PPCh. 23 - Prob. 50PPCh. 23 - Prob. 51PPCh. 23 - Prob. 52PPCh. 23 - Prob. 53PPCh. 23 - Prob. 54PPCh. 23 - Prob. 55PPCh. 23 - Prob. 56PPCh. 23 - Prob. 57PPCh. 23 - Prob. 58PPCh. 23 - Prob. 59PPCh. 23 - Prob. 60PPCh. 23 - Prob. 61PPCh. 23 - Prob. 62PPCh. 23 - Prob. 63PPCh. 23 - Prob. 64PPCh. 23 - Prob. 65PPCh. 23 - Prob. 66PPCh. 23 - Prob. 67PPCh. 23 - Prob. 68PPCh. 23 - Prob. 69PPCh. 23 - Prob. 70PPCh. 23 - Prob. 71PPCh. 23 - Prob. 72PPCh. 23 - Prob. 73PPCh. 23 - Prob. 74PPCh. 23 - Prob. 75PPCh. 23 - Prob. 76PPCh. 23 - Prob. 77IPCh. 23 - Prob. 78IPCh. 23 - Prob. 79IPCh. 23 - Prob. 80IPCh. 23 - Prob. 81IPCh. 23 - Prob. 82IPCh. 23 - Prob. 83IPCh. 23 - Prob. 84IPCh. 23 - Prob. 85IPCh. 23 - Prob. 86IPCh. 23 - Prob. 87IPCh. 23 - Prob. 88IPCh. 23 - Prob. 89IPCh. 23 - Prob. 90IPCh. 23 - Prob. 91CPCh. 23 - Prob. 92CPCh. 23 - Prob. 93CPCh. 23 - Prob. 94CPCh. 23 - Prob. 95CPCh. 23 - Prob. 96CPCh. 23 - Prob. 97CPCh. 23 - Prob. 98CP
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