But-2-yne (CH3-C≡C-CH3) is treated along two parallel pathways. Path 1: catalytic hydrogenation over Pd-BaSO4 gives compound X; X is then reacted with Br2 in CCl4 to give product Z. Path 2: reduction with Na in liquid NH3 gives compound Y; Y is then reacted with Br2 in CCl4 to give product

Question

But-2-yne (CH3-C≡C-CH3) is treated along two parallel pathways. Path 1: catalytic hydrogenation over Pd-BaSO4 gives compound X; X is then reacted with Br2 in CCl4 to give product Z. Path 2: reduction with Na in liquid NH3 gives compound Y; Y is then reacted with Br2 in CCl4 to give product A. What is the total number of distinct organic compounds represented by Z and A together?

Accepted Answer

3. Lindlar hydrogenation yields cis-but-2-ene; anti addition of Br2 gives the meso product (Z = 1 compound). Birch reduction gives trans-but-2-ene; anti addition of Br2 gives the racemic pair (A = two enantiomers). Total distinct compounds Z + A = 1 + 2 = 3.

Solution

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