Organic Chemistry Third Edition + Electronic Solutions Manual And Study Guide
Organic Chemistry Third Edition + Electronic Solutions Manual And Study Guide
3rd Edition
ISBN: 9781119351610
Author: David Klein
Publisher: Wiley Plus
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Chapter 20, Problem 85IP

(a)

Interpretation Introduction

Interpretation: The possible side products in the direct conversion of compound 1 to compound 3 have to be identified.

Concept Introduction:

Hydrolysis of alkyl halides:

Using water or hydroxide as nucleophile, alkyl halides can be converted into alcohols. The overall reaction is known as hydrolysis of alkyl halides.

General Scheme:

R-X+NaOHH2O/refluxR-OH+NaBrAlkylAlcoholhalide

Hydrolysis of nitriles:

Nitriles on hydrolysis get converted into carboxylic acids.

General scheme:

Organic Chemistry Third Edition + Electronic Solutions Manual And Study Guide, Chapter 20, Problem 85IP , additional homework tip  1

(b)

Interpretation Introduction

Interpretation: A complete mechanism for the given two step synthesis has to be drawn

Concept Introduction:

SN2 reaction:

  • It is a bimolecular reaction where breaking and making of bond undergoes in a single step.
  • The nucleophile attacks from the backside of electrophilic carbon and forms a bond between carbon and nucleophile. At the same time, the bond between carbon and leaving group breaks.

General mechanism for SN2 reaction:

Organic Chemistry Third Edition + Electronic Solutions Manual And Study Guide, Chapter 20, Problem 85IP , additional homework tip  2

Hydrolysis of ester:

Esters on hydrolysis get converted into carboxylic acids.

General scheme:

Organic Chemistry Third Edition + Electronic Solutions Manual And Study Guide, Chapter 20, Problem 85IP , additional homework tip  3

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Chapter 20 Solutions

Organic Chemistry Third Edition + Electronic Solutions Manual And Study Guide

Ch. 20.5 - Prob. 11CCCh. 20.6 - Prob. 12CCCh. 20.6 - Prob. 13CCCh. 20.7 - Prob. 1LTSCh. 20.7 - Prob. 14PTSCh. 20.7 - Prob. 15ATSCh. 20.8 - Prob. 16CCCh. 20.8 - Prob. 17CCCh. 20.8 - Prob. 18CCCh. 20.9 - Prob. 19CCCh. 20.10 - Prob. 20CCCh. 20.10 - Prob. 21CCCh. 20.11 - Prob. 22CCCh. 20.11 - Prob. 23CCCh. 20.12 - Prob. 24CCCh. 20.12 - Prob. 25CCCh. 20.12 - Prob. 26CCCh. 20.13 - Prob. 27CCCh. 20.13 - Prob. 28CCCh. 20.13 - Prob. 29CCCh. 20.14 - Prob. 2LTSCh. 20.14 - Prob. 30PTSCh. 20.14 - Prob. 31ATSCh. 20.14 - Prob. 3LTSCh. 20.14 - Prob. 32PTSCh. 20.14 - Prob. 33ATSCh. 20.15 - Prob. 34CCCh. 20 - Prob. 35PPCh. 20 - Prob. 36PPCh. 20 - Prob. 37PPCh. 20 - Prob. 38PPCh. 20 - Prob. 39PPCh. 20 - Prob. 40PPCh. 20 - Prob. 41PPCh. 20 - Prob. 42PPCh. 20 - Prob. 43PPCh. 20 - Prob. 44PPCh. 20 - Prob. 45PPCh. 20 - Prob. 46PPCh. 20 - Prob. 47PPCh. 20 - Prob. 48PPCh. 20 - Prob. 49PPCh. 20 - Prob. 50PPCh. 20 - Prob. 51PPCh. 20 - Prob. 52PPCh. 20 - Prob. 53PPCh. 20 - Prob. 54PPCh. 20 - Prob. 55PPCh. 20 - Prob. 56PPCh. 20 - Prob. 57PPCh. 20 - Prob. 58PPCh. 20 - Prob. 59PPCh. 20 - Prob. 60PPCh. 20 - Prob. 61PPCh. 20 - Prob. 62PPCh. 20 - Prob. 63PPCh. 20 - Prob. 64PPCh. 20 - Prob. 65PPCh. 20 - Prob. 66PPCh. 20 - Prob. 67PPCh. 20 - Prob. 68PPCh. 20 - Prob. 69PPCh. 20 - Prob. 70IPCh. 20 - Prob. 72IPCh. 20 - Prob. 73IPCh. 20 - Prob. 74IPCh. 20 - Prob. 75IPCh. 20 - Prob. 76IPCh. 20 - Prob. 77IPCh. 20 - Prob. 78IPCh. 20 - Prob. 79IPCh. 20 - Prob. 80IPCh. 20 - Prob. 81IPCh. 20 - Prob. 82IPCh. 20 - Prob. 83IPCh. 20 - Prob. 84IPCh. 20 - Compound 3 (below) was used as an intermediate in...Ch. 20 - The m- and p-substituted methyl benzoates listed...Ch. 20 - Prob. 87IPCh. 20 - Prob. 88IPCh. 20 - Prob. 89IPCh. 20 - Prob. 90CPCh. 20 - Prob. 91CPCh. 20 - Prob. 92CPCh. 20 - Prob. 93CP
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