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Question

How many dichlorocyclohexane would be obtained on chlorination of chlorocyclohexane (including stereoisomers)?

A
4
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B
6
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C
8
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D
9
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Solution

The correct option is B 9

Chlorination of chlorocyclohexane gives total 9 dichlorocyclohexanes.
Chlorination replaces one H atom by one Cl atom. There are four types of hydrogens with respect to previous Cl.

Product 1 - Does not have any chiral carbon so only one product
Product 2 - Two chiral centres so RR, RS, SS isomers possible.
Product 3 - Two chiral centres so RR, RS, SS isomers possible.
Product 4 - Two chiral centres but plane of symmetry exists so only two isomers possible.

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