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Preparation of Alkyl Halides

A hydrocarbon...

Question

A hydrocarbon $C_{5} H_{10}$ does not react with chlorine in dark but gives a single monochloro compound $C_{5} H_{9} C l$ in bright sunlight. Identify the hydrocarbon.

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Solution

Molecular formula $C_{5} H_{10}$ can be either alkene or cycloalkane.

Since, the hydrocarbon does not react with chlorine in dark, it is not an alkene. So, it is a cycloalkane, i.e., cyclopentane.

Since, it forms only single monochloro derivative in bright sunlight, all the H - atoms should be identical So, it is cyclopentane.

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