Question

An achiral hydrocarbon A of molecular formula C7H12 reacts with two equivalents of H2 in the presence of Pd-C to form CH3CH2CH2CH2CH(CH3)2. One oxidative cleavage product formed by the treatment of A with O3 is CH3COOH. Reaction of A with H2 and Lindlar catalyst forms B, and reaction of A with Na, NH3 forms C. Identify compounds A, B, and C. Be sure to answer all parts.

Answer 1

Answer:

A) 5-methylhex-2-yne

B) (2Z)-5-methylhex-2-ene

C) (2E)-5-methylhex-2-ene

Explanation:

The given compound must be alkyne as it is undergoing reduction with two equivalents of hydrogen molecule.

Also as it is giving acetic acid on oxidative ozonolysis, it must have triple bond after two carbons in the chain.

The structure of hydrocarbon formed after reduction will give us the structure of alkyne by these information.

Reaction with hydrogen molecule in presence of Lindlar's catalyst gives cis alkene.

Reaction with hydrogen molecule in presence of Na, ammonia gives trans alkene.

The structure of compound is shown in the figure