Explain reaction of sodium acetylide of dibromododecane

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Reference no: EM13209019

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 compound with the following chemical formula: HO2C(CH2)12COOH (a diacid because it has two acid functional groups on each end). Catalytic hydrogenation of compound B over Lindar palladium gave compound C (C14H26) and hydrogenation of compound B over platinum gave compound D (C14H28). Sodium-ammonia reaction 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.

Reference no: EM13209019

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