Question: Compound A has the molecular formula C14H25Br and was obtained by reaction of sodium acetylide with 1,12-dibromododecane. On treatment of compound A with sodium amide,

Compound A has the molecular formula C14H25Br and was obtained by reaction of sodium acetylide with 1,12-dibromododecane. On treatment of compound A with sodium amide, it was converted to compound B (C14H24). Ozonolysis of compound B gave the diacid HO2C(CH2)12CO2H. Catalytic hydrogenation of compound B over Lindlar palladium gave compound C (C14H26), and hydrogenation over platinum gave compound D (C14H28). Sodium-ammonia reduction of compound B gave compound E (C14H26). Both C and E yielded O≡CH(CH2)12CH≡O on ozonolysis. Assign structures to compounds A through E so as to be consistent with the observed transformations.

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