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Question
Among the isomeric alkanes of molecular formula C5H12, identify the one that on photochemical chlorination yields three isomeric monochlorides.
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Solution
\[\ce{\underset{n-pentane}{CH3 - CH2 - CH2 - CH2 - CH3}}\]
\[\ce{\overset{a}{C}H3\overset{b}{C}H2\overset{c}{C}H2\overset{b}{C}H2\overset{a}{C}H3}\] has three sets of identical H-atoms, denoted as a, b and c. Displacement of any identical hydrogen from each set gives the same product. Hence, three isomeric monochlorides are possible.
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