Question

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

• A. $4$
• B. $6$
• C. $8$
• D. $9$

Answer 1

Answer: (D)

$9$

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.