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Preparation of Alkyl Halides

A hydrocarbon...

Question

A hydrocarbon having molecular weight 70 gives a single monochloride on chlorination. How many dichlorides will be formed (including stereoisomers) on photodichlorination of the hydrocarbon?

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Solution

Molecular formula of the hydrocarbon for the given mass would be $C_{5} H_{10}$
Double bond equivalent of $C_{5} H_{10}$ is 1.
So the possible isomers of the compound may be:

Among the isomers, only cyclopentane can give single monochloride on chlorination.
Hence upon photodichlorination of the cyclopentate, total seven dichlorides can be formed.

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