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Isomerisation of Alkanes

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Question

Suggest a sequence of reactions suitable for preparing following compound from the indicated starting material. You may use any necessary organic or inorganic reagents.
$T r a n s - 1, 2 -$ dichlorocyclopentane from cyclopentane.

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Solution

Free radical chlorination of cyclopentane in presence of light gives cyclopentyl chloride. Dehydrochlorination with alcoholic $K O H$ gives cyclopentene. Chlorination with chlorine in presence of carbon tetrachloride gives trans 1,2-dichlorocyclopentane.

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