An alkyl halide X undergoes Wurtz reaction to yield an alkane Y with the molecular formula C ₆ H ₁₄ . Alkane Y , upon photochemical monochlorination, yields exactly two structural isomers. Identify the starting alkyl halide X .

Step-by-step solution

The alkane Y has the formula C ₆ H ₁₄ . Since it yields exactly two structural isomers upon monochlorination, it must possess exactly two distinct sets of equivalent hydrogen atoms. Let us evaluate the possible symmetrical hexanes formed via Wurtz reaction: First, n -hexane (from 1-chloropropane) has three sets of equivalent hydrogens, yielding 3 monochloro isomers. Second, 2,3-dimethylbutane (from 2-chloropropane) has 12 equivalent primary hydrogens and 2 equivalent tertiary hydrogens. It yields exactly 2 monochlo