Organic Chemistry (8th Edition)

Published by Pearson
ISBN 10: 0321768418
ISBN 13: 978-0-32176-841-4

Chapter 4 - The Study of Chemical Reactions - Problems - Page 137: Problem 4-4 a

Answer

The explanation is given below.

Work Step by Step

As we can see, the twelve hydrogen atoms of cyclohexene are on equivalent$2^{\circ}$ carbon atoms. Replacement of any of these hydrogen atoms will lead to the same product, chlorocyclohexane. But in hexane, the hydrogen atoms are on three different carbon atoms - C1/C6, C2/C5, C3/C4. So, chlorination of hexane gives a mixture of all possible isomers 1-, 2-, and 3-chlorohexane.
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