Single correct option
But-2-yne () is converted in two ways. Route 1: (i) ; (ii) ; (iii) one equivalent of alcoholic (E2, anti-periplanar elimination), giving . Route 2: (i) , Lindlar catalyst; (ii) (anti addition); (iii) one equivalent of alcoholic , giving . and are 2-bromobut-2-enes. Which statement is correct?
- A. is the isomer and is the isomer
- B. is the isomer and is the isomer
- C. Both and are the isomer
- D. Both and are the isomer
Show answer and solution
Answer: (B) is the isomer and is the isomer
Route 1: dissolving-metal reduction gives trans-but-2-ene; anti addition of to a trans alkene gives meso-2,3-dibromobutane (). Route 2: Lindlar reduction gives cis-but-2-ene; anti addition of bromine gives the racemic (/) dibromide. For E2 the and removed must be anti-periplanar. Placing the meso dibromide in the conformation with (on C2) anti to (on C3) puts the two methyl groups gauche, so they end up cis on the new double bond. On C3 the higher priority group is and on C2 it is ; with the methyls cis these lie on opposite sides, which is the isomer. The racemic dibromide, by the same analysis, has its methyls anti and gives the isomer. So P is and Q is , option B.
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