Organic Chemistry
Organic Chemistry
2nd Edition
ISBN: 9781118452288
Author: David R. Klein
Publisher: WILEY
Question
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Chapter 22.2, Problem 9CC

(a)

Interpretation Introduction

Interpretation:

To predict the major product in the given set of reactions and propose a mechanism for the same.

Concept introduction:

Under acid catalyzed conditions the carbonyl group gets protonated and gives a resonance stabilized intermediate resulting in formation of enol by deprotonation.  The enol undergoes bromination to give an α -bromoketone or α -bromoaldehyde (acid-catalyzed halogenation) which then undergoes E2 elimination when treated with pyridine to form α,β unsaturated ketone and α,β unsaturated aldehyde respectively depending upon the starting material taken.

(b)

Interpretation Introduction

Interpretation:

To predict the major product in the given set of reactions and propose a mechanism for the same.

Concept introduction:

Under acid catalyzed conditions the carbonyl group gets protonated and gives a resonance stabilized intermediate resulting in formation of enol by deprotonation.  The enol undergoes bromination to give an α -bromoketone or α -bromoaldehyde (acid-catalyzed halogenation) which then undergoes E2 elimination when treated with pyridine to form α,β unsaturated ketone and α,β unsaturated aldehyde respectively depending upon the starting material taken.

(c)

Interpretation Introduction

Interpretation:

To predict the major product in the given set of reactions and propose a mechanism for the same.

Concept introduction:

Under acid catalyzed conditions the carbonyl group gets protonated and gives a resonance stabilized intermediate resulting in formation of enol by deprotonation.  The enol undergoes bromination to give an α -bromoketone or α -bromoaldehyde (acid-catalyzed halogenation) which then undergoes E2 elimination when treated with pyridine to form α,β unsaturated ketone and α,β unsaturated aldehyde respectively depending upon the starting material taken.

Blurred answer

Chapter 22 Solutions

Organic Chemistry

Ch. 22.2 - Prob. 10CCCh. 22.2 - Prob. 11CCCh. 22.2 - Prob. 12CCCh. 22.2 - Prob. 13CCCh. 22.2 - Prob. 14CCCh. 22.3 - Prob. 2LTSCh. 22.3 - Prob. 15PTSCh. 22.3 - Prob. 16PTSCh. 22.3 - Prob. 17ATSCh. 22.3 - Prob. 18ATSCh. 22.3 - Prob. 19ATSCh. 22.3 - Prob. 3LTSCh. 22.3 - Prob. 20PTSCh. 22.3 - Prob. 21ATSCh. 22.3 - Prob. 22ATSCh. 22.3 - Prob. 4LTSCh. 22.3 - Prob. 23PTSCh. 22.3 - Prob. 24ATSCh. 22.3 - Prob. 25CCCh. 22.3 - Prob. 26CCCh. 22.3 - Prob. 27CCCh. 22.4 - Prob. 28CCCh. 22.4 - Prob. 29CCCh. 22.4 - Prob. 30CCCh. 22.4 - Prob. 31CCCh. 22.4 - Prob. 32CCCh. 22.5 - Prob. 33CCCh. 22.5 - Prob. 34CCCh. 22.5 - Prob. 5LTSCh. 22.5 - Prob. 35PTSCh. 22.5 - Prob. 36ATSCh. 22.5 - Prob. 37ATSCh. 22.5 - Prob. 38ATSCh. 22.5 - Prob. 6LTSCh. 22.5 - Prob. 39PTSCh. 22.5 - Prob. 40ATSCh. 22.5 - Prob. 41ATSCh. 22.5 - Prob. 42ATSCh. 22.5 - Prob. 43ATSCh. 22.6 - Prob. 44CCCh. 22.6 - Prob. 45CCCh. 22.6 - Prob. 46CCCh. 22.6 - Prob. 7LTSCh. 22.6 - Prob. 47PTSCh. 22.6 - Prob. 48ATSCh. 22.6 - Prob. 49CCCh. 22.6 - Prob. 50CCCh. 22.7 - Prob. 8LTSCh. 22.7 - Prob. 51PTSCh. 22.7 - Prob. 52PTSCh. 22.7 - Prob. 53ATSCh. 22.7 - Prob. 9LTSCh. 22.7 - Prob. 54PTSCh. 22.7 - Prob. 55ATSCh. 22.7 - Prob. 56ATSCh. 22 - Prob. 57PPCh. 22 - Prob. 58PPCh. 22 - Prob. 59PPCh. 22 - Prob. 60PPCh. 22 - Prob. 61PPCh. 22 - Prob. 62PPCh. 22 - Prob. 63PPCh. 22 - Prob. 64PPCh. 22 - Prob. 65PPCh. 22 - Prob. 66PPCh. 22 - Prob. 67PPCh. 22 - Prob. 68PPCh. 22 - Prob. 69PPCh. 22 - Prob. 70PPCh. 22 - Prob. 71PPCh. 22 - Prob. 72PPCh. 22 - Prob. 73PPCh. 22 - Prob. 74PPCh. 22 - Prob. 75PPCh. 22 - Prob. 76PPCh. 22 - Prob. 77PPCh. 22 - Prob. 78PPCh. 22 - Prob. 79PPCh. 22 - Prob. 80PPCh. 22 - Prob. 81PPCh. 22 - Prob. 82PPCh. 22 - Prob. 83PPCh. 22 - Prob. 84PPCh. 22 - Prob. 85PPCh. 22 - Prob. 86PPCh. 22 - Prob. 87PPCh. 22 - Prob. 88PPCh. 22 - Prob. 89PPCh. 22 - Prob. 90PPCh. 22 - Prob. 91PPCh. 22 - Prob. 92PPCh. 22 - Prob. 93PPCh. 22 - Prob. 94PPCh. 22 - Prob. 95PPCh. 22 - Prob. 96PPCh. 22 - Prob. 97PPCh. 22 - Prob. 98PPCh. 22 - Prob. 99PPCh. 22 - Prob. 100IPCh. 22 - Prob. 101IPCh. 22 - Prob. 102IPCh. 22 - Prob. 103IPCh. 22 - Prob. 104IPCh. 22 - Prob. 105IPCh. 22 - Prob. 106IPCh. 22 - Prob. 107IPCh. 22 - Prob. 108IPCh. 22 - Prob. 109IPCh. 22 - Prob. 110IPCh. 22 - Prob. 111IPCh. 22 - Prob. 112IP
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