n-Butylcyclohexane is prepared via the reaction sequence: X - (PCl5 / 0 deg C) - Y - (NaNH2, excess) - Z - (i) NaNH2, (ii) n-C4H9I, (iii) H2/Pt, heat, pressure - n-Butylcyclohexane. Identify compound X.

Question

n-Butylcyclohexane is prepared via the reaction sequence: X -> (PCl5 / 0 deg C) -> Y -> (NaNH2, excess) -> Z -> (i) NaNH2, (ii) n-C4H9I, (iii) H2/Pt, heat, pressure -> n-Butylcyclohexane. Identify compound X.

Accepted Answer

C6H5COCH3. Retrosynthesis: n-butylcyclohexane <- H2/Pt/heat <- Ph-C=C-C4H9 (1-phenylpent-1-yne) <- Ph-C=C⁻ + n-C4H9I <- Ph-C=CH (phenylacetylene = Z) <- NaNH2 double elimination <- Ph-CCl2-CH3 (Y) <- PCl5/0 deg C <- C6H5COCH3 (acetophenone = X).

n-Butylcyclohexane is prepared via the reaction sequence: X -> (PCl5 / 0 deg C) -> Y -> (NaNH2, excess) -> Z -> (i) NaNH2, (ii) n-C4H9I, (iii) H2/Pt, heat, pressure -> n-Butylcyclohexane. Identify compound X.

Solution

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