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A hydrocarbon P has molecular formula C8...

A hydrocarbon P has molecular formula `C_8H_(16)`, and it does not undergo hydrogenation with raney Ni. A on free radical chlorination yields three monochloro derivatives Q, R and S (all structural isomers) with their molecular formula `C_8 H_(15)Cl`. Only Q can show optical isomerism R. On further chlorination produces a dichloride `C_8 H_(14) Cl_2`, as one of the several isomers which on heating with sodium metal in etheral solution gives bicyclo [2, 2, 2] octane.
Which of the following satisfy the criteria for P?

A

B

C

D

Text Solution

Verified by Experts

The correct Answer is:
D
It gives three positioned isomers on mono chlorination
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A hydrocarbon P has molecular formula C_8H_(16) , and it does not undergo hydrogenation with raney Ni. A on free radical chlorination yields three monochloro derivatives Q, R and S (all structural isomers) with their molecular formula C_8 H_(15)Cl . Only Q can show optical isomerism R. On further chlorination produces a dichloride C_8 H_(14) Cl_2 , as one of the several isomers which on heating with sodium metal in etheral solution gives bicyclo [2, 2, 2] octane. How many stereoisomers are possible for Q?

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