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In the presence of a small amount of bromine, cyclohexene

Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr ISBN: 9780321768414 33

Solution for problem 25P Chapter 4

Organic Chemistry | 8th Edition

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Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr

Organic Chemistry | 8th Edition

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Problem 25P

In the presence of a small amount of bromine, cyclohexene undergoes the following light promoted reaction:

(a) Propose a mechanism for this reaction.

(b) Draw the structure of the rate-limiting transition state.

Step-by-Step Solution:

Solution 25P

Step 1 </p>

When cyclohexene is reacted with small amounts of bromine in the presence of light, it undergoes the free-radical substitution of bromine on the cyclohexene ring resulting in the formation of 3-Bromocyclohexene.

The reaction is as follows:

Step 2 </p>

(a)

The mechanism for the reaction is as follows:

Initiation: Bromine molecule in the presence of light cleaves homolytically and forms bromine free radicals.

The reaction is as follows:

Step 3 </p>

Propagation: This steep involves two steps. They are as follows:

Step I: Cleavage of the more weak  of the cyclic ring takes place resulting in the formation of a stable allylic free-radical.

The reaction is as follows:

Step 4 </p>

Step II: The stable allylic free-radical reacts with the molecular Bromine and forms bromine substituted cyclohexene ring and bromine free radical.

The reaction is as follows:

Step 5 of 7

Chapter 4, Problem 25P is Solved
Step 6 of 7

Textbook: Organic Chemistry
Edition: 8
Author: L.G. Wade Jr
ISBN: 9780321768414

This textbook survival guide was created for the textbook: Organic Chemistry, edition: 8. The full step-by-step solution to problem: 25P from chapter: 4 was answered by , our top Chemistry solution expert on 05/06/17, 06:41PM. Since the solution to 25P from 4 chapter was answered, more than 1052 students have viewed the full step-by-step answer. Organic Chemistry was written by and is associated to the ISBN: 9780321768414. This full solution covers the following key subjects: reaction, promoted, cyclohexene, draw, light. This expansive textbook survival guide covers 25 chapters, and 1336 solutions. The answer to “In the presence of a small amount of bromine, cyclohexene undergoes the following light promoted reaction: (a) Propose a mechanism for this reaction.(b) Draw the structure of the rate-limiting transition state.” is broken down into a number of easy to follow steps, and 31 words.

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