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Question:

Which branched-chain isomer of the hydrocarbon with molecular mass 72 u gives only one isomer of mono-substituted alkyl halide?

Neohexane

Tertiary butyl chloride

Neopentane

Isohexane

Solution:

Neopentane, when reacted with Cl2 and undergoes monohalogenation, gives a single product. This is because all the hydrogen atoms in neopentane are equivalent. Replacing any one of them with a chlorine atom results in the same 2-chloro-2-methylpropane (also known as tert-pentyl chloride).