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Question
Among the isomeric alkanes of molecular formula C5H12, identify the one that on photochemical chlorination yields four isomeric monochlorides.
Solution
\[\begin{array}{cc}
\ce{\overset{a}{C}H3 - \overset{b}{C}H - \overset{c}{C}H2 - \overset{d}{C}H3}\\
|\phantom{.........}\\
\ce{\overset{a}{C}H3}\phantom{.......}
\end{array}\]
Four types of equivalent H-atoms are present, labelled a, b, c, and d. Hence, four isomeric monochlorides are possible.
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