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, Problem 81IP
Interpretation Introduction

Interpretation: A synthesis of phenacetin starting from benzene has to be found

Concept Introduction:

Electrophilic aromatic substitution: Electrophilic aromatic substitution is a reaction in which the hydrogen atom of an aromatic ring is replaced as a result of an electrophilic attack on the aromatic ring.  There are three general steps involved in an electrophilic aromatic substitution.

Williamson ether synthesis: The Williamson ether synthesis is a reaction that converts alcohols (R−OH) into ethers (R−O−R). The first step in this reaction is forming the conjugate base of the alcohol (called an alkoxide) by reacting the alcohol with sodium metal. This reaction forms hydrogen gas (H2) as a bi-product.

Organic Chemistry, Binder Ready Version, Chapter 23, Problem 81IP , additional homework tip  1

The alkoxide can then be added to a suitable alkyl halide (typically a primary halide) to form the ether via an SN2 mechanism.

Organic Chemistry, Binder Ready Version, Chapter 23, Problem 81IP , additional homework tip  2

To find: Give a synthesis of phenacetin starting from benzene

Apply a retrosynthetic analysis

Organic Chemistry, Binder Ready Version, Chapter 23, Problem 81IP , additional homework tip  3

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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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