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Compound A has the molecular formula C14H25Br\mathrm{C}_{14} \mathrm{H}_{25} \mathrm{Br} 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\mathrm{C}_{14} \mathrm{H}_{24}). Ozonolysis of compound B gave the diacid HO2C(CH2)12CO2H\mathrm{HO}_{2} \mathrm{C}\left(\mathrm{CH}_{2}\right)_{12} \mathrm{CO}_{2} \mathrm{H}. Catalytic hydrogenation of compound B over Lindlar palladium gave compound C (C14H26\mathrm{C}_{14} \mathrm{H}_{26}), and hydrogenation over platinum gave compound D (C14H28\mathrm{C}_{14} \mathrm{H}_{28}). C yielded OCH(CH2)12CHO\mathrm{O} \square \mathrm{CH}\left(\mathrm{CH}_{2}\right)_{12} \mathrm{CH} \square \mathrm{O} on ozonolysis. Assign structures to compounds A through D so as to be consistent with the observed transformations.


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Acetylide is a strong nucleophile\text{\textcolor{#c34632}{Acetylide is a strong nucleophile}} and reaction undergoes nucleophilic substitution\textbf{nucleophilic substitution} with Br\text{\textcolor{#4257b2}{Br}} being a leaving group (LG). Molecule is symmetric so it doesn't matter which carbon is attacked, product will be the same.

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