Question

Compound A, C6H8, absorbed 3 equivalents of H2 on catalytic hydrogenation over a Pd/C catalyst to give B (C6H14). On ozonolysis, compound A gave, among other things, a ketone which was identified as acetone. On treatment with NaNH2 in NH3, followed by addition of iodomethane, compound A gave a new hydrocarbon, C (C7H10). Draw the structure of compound C.

Answer 1

The structural formula of Compound C is CH₂(CH)₅CH₃.

Step-by-step explanation:

Compound A is an alkene called Hexatriene, that is, it has three double bonds within its structure. Hydrogen atom is removed when compound A reacts with NaNH₂ in ammonia. Further reaction with iodomethane replaces the hydrogen atom with a methyl group from the iodomethane to form compound C.

Here is the step-wise mechanism:

CH₂(CH)₄CH₂ (With NaNH₂ in NH₃)...........> CH₂(CH)₄CH⁻ + H⁺

CH₂(CH)₄CH⁻ + CH₃I (Iodomethane) ...........> CH₂(CH)₅CH₃ + I⁻

Compound C is called 1, 3, 5-Heptatriene.