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Free-radical chlorination of hexane gives very poor yields

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

Solution for problem 4P 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 4P

Free-radical chlorination of hexane gives very poor yields of 1-chlorohexane, while cyclohexanecan be converted to chlorocyclohexane in good yield.

(a) How do you account for this difference?

(b) What ratio of reactants (cyclohexane and chlorine) would you use for the synthesis ofchlorocyclohexane?

Step-by-Step Solution:

Solution 4P:

Here, we are going to discuss about the difference of Free-radical chlorination of hexane gives very poor yields of 1-chlorohexane, while cyclohexane can be converted to chlorocyclohexane in good yield.

Step 1: (a)

The free radical reaction of hexane is given as follows

In hexane, three different types of Hydrogen atoms are present.

Carbon-1(equivalent to Carbon 6)Carbon-2(equivalent to Carbon 5)Carbon-3(equivalent to Carbon 4)

Therefore, monochlorination of hexane gives a mixture which contain three isomers: 1-chlorohexane, 2-chlorohexane and 3-chlorohexane.

Whereas, in case of cyclohexane, all the hydrogen atoms are equivalent to 2o. Therefore, chlorination of cyclohexane leads to the formation of same product : chlorocyclohexane. Thus it has in good yield.

Step 2 of 2

Chapter 4, Problem 4P is Solved
Textbook: Organic Chemistry
Edition: 8
Author: L.G. Wade Jr
ISBN: 9780321768414

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