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.

Question

Roger Blanchard

Chemistry

30 January, 19:17

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.

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Romeo Anthony · Answer 1

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

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.