Question

An optically active alkyne A (C10H14) can be catalytically hydrogenated to butylcyclohexane. Treatment of A with C2H5MgBr liberates no gas. Catalytic hydrogenation of A over Pd/C in the presence of quinoline poison and treatment of the product B with O3 and then H2O2 gives an optically active tricarboxylic acid C8H12O6. (A tricarboxylic acid is a compound with three –CO2H groups.) Give the structure of A (without stereochemistry).

Answer 1

Answer:

The reverse process, hydrogenation, can be performed in the presence of a catalyst like metallic platinum. Hydrogen gas reacts with the metal surface, breaking the hydrogen-hydrogen bond to form weaker metal-hydrogen bonds. An alkene or alkyne can then react with the metal in a similar manner, then form stronger bonds with two or more hydrogen

Explanation:

Answer 2

The structure of the optically active alkyne A is shown in the image attached  (without stereochemistry).

An alkyne contains a carbon - carbon triple bond. We have been told that the starting alkyne is optically active and that means that the compound is not symmetrical.

It was first hydrogenated using Pd/C in the presence of quinoline poison to give product B which is an alkene. The alkene now undergoes ozonoation in the presence of hydrogen peroxide to yield the tricarboxylic acid C8H12O6.

Based on all these, the structure of A (without stereochemistry) is shown in the image attached.

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