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For each compound, predict the major product of

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

Solution for problem 46SP 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 46SP

For each compound, predict the major product of free-radical bromination. Remember that bromination is highly selective, and only the most stable radical will be formed.

(a) cyclohexane

(b) methylcyclopentane

(c) decalin

(d) hexane

(e)

(f)

Step-by-Step Solution:
Step 1 of 3

Solution 46SP

The stability of radical increases as the number of alkyl groups bonded to the radical carbon increases.

The allylic radical is more stable than the other radicals because two resonance structures can be drawn.

Allylic radical is more stable than tertiary radical, and a secondary radical is more stable than a primary radical.

(a)

Treatment of cyclohexene with bromine in the presence of light gives bromocyclohexane. Thus, the reaction is as follows:

(b)

Treatment of methylcyclopentane with bromine in the presence of light gives 1-bromo-1-methylcyclopentane. Thus, the reaction is as follows:

(c)

Treatment of decalin with bromine in the presence of light gives 4a-bromo decahydronaphthalene. Thus, the reaction...

Step 2 of 3

Chapter 4, Problem 46SP is Solved
Step 3 of 3

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

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