Organic Chemistry
Organic Chemistry
2nd Edition
ISBN: 9781118452288
Author: David R. Klein
Publisher: WILEY
Question
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Chapter 8, Problem 75PP
Interpretation Introduction

Interpretation:

The formation Hofmann product exclusively in the given reaction even though the base is not sterically hindered is needed to be explained.

Concept introduction:

In an elimination reaction, alkenes are formed when alkyl halides are treated with bases via eliminating one β-proton and one α-halo group (leaving group) of the alkyl halide.

E2 elimination reaction of cyclohexane compounds: E2 elimination occurs in a cyclohexane compound when the leaving group is antiperiplanar to the proton in presence of strong base. If the leaving group is on wedge then the β-proton should be in dash line to achieve the antiperiplanarity in cyclohexane.

The bulkiness of the base controls the regioselectivity in an elimination reaction. According to Zaitsev product rule the more substituted alkene is formed from non-sterically hindered base. According to Hofmann product rule the less substituted alkene is formed from sterically hindered base.

The product of the elimination reaction is depends upon the β-positions of alkyl halide. If the β-positions are identical and the products formed are also identical. If the β-positions are different and the products formed are also different. This means the double bond can form in two different regions so this type of reaction is called regioselective and the products are called as regiochemical outcomes.

To explain: The exclusive Hofmann product of given reaction yield even though the base is not sterically hindered.

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Chapter 8 Solutions

Organic Chemistry

Ch. 8.5 - Prob. 8PTSCh. 8.6 - Prob. 4LTSCh. 8.6 - Prob. 9PTSCh. 8.6 - Prob. 10PTSCh. 8.6 - Prob. 11ATSCh. 8.6 - Prob. 12ATSCh. 8.7 - Prob. 13CCCh. 8.7 - Prob. 14CCCh. 8.7 - Prob. 5LTSCh. 8.7 - Prob. 15PTSCh. 8.7 - Prob. 16ATSCh. 8.7 - Prob. 17ATSCh. 8.7 - Prob. 6LTSCh. 8.7 - Prob. 18PTSCh. 8.7 - Prob. 19ATSCh. 8.7 - Prob. 20CCCh. 8.7 - Prob. 21CCCh. 8.8 - Prob. 7LTSCh. 8.8 - Prob. 22PTSCh. 8.8 - Prob. 23ATSCh. 8.8 - Prob. 24ATSCh. 8.8 - Prob. 25ATSCh. 8.9 - Prob. 26CCCh. 8.9 - Prob. 27CCCh. 8.9 - Prob. 28CCCh. 8.9 - Prob. 8LTSCh. 8.9 - Prob. 29PTSCh. 8.9 - Prob. 31CCCh. 8.10 - Prob. 32CCCh. 8.10 - Prob. 33CCCh. 8.10 - Prob. 9LTSCh. 8.10 - Prob. 34PTSCh. 8.10 - Prob. 35ATSCh. 8.10 - Prob. 36ATSCh. 8.11 - Prob. 37CCCh. 8.11 - Prob. 38CCCh. 8.12 - Prob. 10LTSCh. 8.13 - Prob. 11LTSCh. 8.14 - Prob. 12LTSCh. 8.14 - Prob. 46PTSCh. 8.14 - Prob. 48ATSCh. 8.14 - Prob. 49ATSCh. 8 - Prob. 50PPCh. 8 - Prob. 51PPCh. 8 - Prob. 52PPCh. 8 - Prob. 53PPCh. 8 - Prob. 54PPCh. 8 - Prob. 55PPCh. 8 - Prob. 56PPCh. 8 - Prob. 57PPCh. 8 - Prob. 58PPCh. 8 - Prob. 59PPCh. 8 - Prob. 60PPCh. 8 - Prob. 61PPCh. 8 - Prob. 62PPCh. 8 - Prob. 63PPCh. 8 - Prob. 64PPCh. 8 - Prob. 65PPCh. 8 - Prob. 66PPCh. 8 - Prob. 67PPCh. 8 - Prob. 68PPCh. 8 - Prob. 69PPCh. 8 - Prob. 70PPCh. 8 - Prob. 71PPCh. 8 - Prob. 72PPCh. 8 - Prob. 73PPCh. 8 - Prob. 74PPCh. 8 - Prob. 75PPCh. 8 - Prob. 76PPCh. 8 - Prob. 77IPCh. 8 - Prob. 78IPCh. 8 - Prob. 79IPCh. 8 - Prob. 80IPCh. 8 - Prob. 81IPCh. 8 - Prob. 82IPCh. 8 - Prob. 83IPCh. 8 - Prob. 84IPCh. 8 - Prob. 85IPCh. 8 - Prob. 86IPCh. 8 - Prob. 87IP
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