How many different monochlorination products (constitutional isomers, ignoring stereoisomers) can the alkane shown form on free-radical chlorination?

Answer: B

Pentane, CH3CH2CH2CH2CH3, has three sets of equivalent hydrogens: the two terminal CH3 groups, the two CH2 next to them, and the central CH2. Each set gives one monochloride (1-, 2- and 3-chloropentane): 3 products (RDKit symmetry classes give 3).

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