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Question
A hydrocarbon C5H10 does not react with chlorine in dark but gives a single monochloro compound C5H9Cl in bright sunlight. Identify the hydrocarbon.
Solution
A hydrocarbon with the molecular formula C5H10 belongs to the group with a general molecular formula CnH2n. Therefore, it may either be an alkene or a cycloalkane.
Since hydrocarbon does not react with chlorine in the dark, it cannot be an alkene. Thus, it should be a cycloalkane.
Further, the hydrocarbon gives a single monochloro compound, C5H9Cl by reacting with chlorine in bright sunlight. Since a single monochloro compound is formed, the hydrocarbon must contain H−atoms that are all equivalent. Also, as all H−atoms of a cycloalkane are equivalent, the hydrocarbon must be a cycloalkane. Hence, the said compound is cyclopentane. The reactions involved are:
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