Organic Chemistry
Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 14.SE, Problem 16VC
Interpretation Introduction

Interpretation:

The structures of all possible adducts obtainable when the diene given reacts with one equivalent of HCl are to be given.

Concept introduction:

Conjugated dienes undergo electrophilic addition reactions through the formation of an allyl carbocation. The allyl cation is resonance stabilized and the attack of chloride ion on each of these forms leads to the formation of a mixture of 1, 2- and 1, 4-addition products.

To give:

The structures of all possible adducts obtainable when the diene given reacts with one equivalent of HCl.

Expert Solution & Answer
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Answer to Problem 16VC

The compound given is 1-vinylcyclopentene.The structures of all the possible adducts obtained when it reacts with one equivalent of HCl are given below.

Organic Chemistry, Chapter 14.SE, Problem 16VC , additional homework tip  1

Explanation of Solution

1-Vinylcyclopentene is an unsymmetrical conjugated diene. Protonation of the CH2 in double bond and that in the ring lead to the formation of two different allyl carbocations, each of which is in resonance with another form. Hence four carbocations as shown are possible. Attack of the chloride ion on each of these carbocation leads to the formation of four different products.

Organic Chemistry, Chapter 14.SE, Problem 16VC , additional homework tip  2

Conclusion

The compound given is 1-vinylcyclopentene.The structures of all the possible adducts obtained, when it reacts with one equivalent of HCl, are given below.

Organic Chemistry, Chapter 14.SE, Problem 16VC , additional homework tip  3

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Chapter 14 Solutions

Organic Chemistry

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