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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.
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Solution
A hydrocarbon with the molecular formula C5H10 belongs to the group with a general molecular formula of CnH2n. Therefore, it may either be an alkene or a cycloalkane. Since hydrocarbons do not react with chlorine in the dark, they cannot be alkenes. 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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\[\begin{array}{cc}
\ce{H3C}\phantom{..................................}\\
\backslash\phantom{...........................}\\
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/\phantom{...........................}\\
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