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Q. Primary alkyl halide $C_4H_9Br$ (A) on reaction with alcoholic $KOH$ gives compound (B). Compound (B) is reacted with $HBr$ to give (C) which is an isomer of (A). When (A) is reacted with sodium metal, it gives compound (D), $C_8H_{18}$ which is different from the compound formed when $n$-butyl bromide is reacted with sodium. The compound (D) is

Haloalkanes and Haloarenes

Solution:

There can be only two primary alkyl bromides with molecular formula, $C_4H_9Br$. These are
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(A) must be isobutyl bromide as, when treated with sodium it gave a compound different than that produced by $n$-butyl bromide, which reacts with sodium to give n-octane
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