A hydrocarbon $A (C_{10} H_{12})$ has no chiral carbon A gives a white precipitate with ammoniacal solution of silver nitrate A on treatment with $H_{2} / P t$ gives $B (C_{10} H_{20})$ A on ozonolysis gives $C (C_{8} H_{12} O_{4})$ as one product which on heating with sodalime gives $D (C_{6} H_{12}) D$ on monochlorination with $C l_{2} / h v$ gives $C_{6} H_{11} C l$ as sole isomer identify A to D.

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Solution

Th hydrogenation of 1,4-diethynylcyclohexane( compound A) in presence of Pt gives 1,4-diethylcyclohexane (compound B). In this reaction, carbon carbon triple bonds are reduced to single bonds.
The ozonolysis of 1,4-diethynylcyclohexane (compound A) gives cyclohexane-1,4-dicarboxylic acid (compound C). In this reaction, the triple bonds are broken to form -COOH groups.
When cyclohexane-1,4-dicarboxylic acid (compound C) is heated with sodalime, decarboxylation gives cyclohexane (compound D). Monochlorination of cyclohexane (compound D) gives monochloro cyclohexane as the sole isomer.

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