One or more options correct
The two geometric isomers of but-2-ene are treated separately with (i) in (anti addition through a bromonium ion) or (ii) cold dilute alkaline or followed by work-up (syn addition). The correct statement(s) about the single compound formed, ignoring any enantiomer produced, is/are
- A. -But-2-ene with gives meso-2,3-dibromobutane
- B. -But-2-ene with gives meso-2,3-dibromobutane
- C. -But-2-ene with cold dilute alkaline gives meso-butane-2,3-diol
- D. -But-2-ene with followed by gives meso-butane-2,3-diol
Show answer and solution
Answer: B, C
Anti addition to the trans alkene and syn addition to the cis alkene both place the two new groups so that the two stereocentres have opposite configurations with a mirror plane in the eclipsed conformation, giving the meso compound. The opposite pairings (anti to cis, syn to trans) give , formed as a racemic mixture of chiral enantiomers. I confirmed this by building the 3D geometry of each addition and assigning CIP labels: trans plus gives , cis plus gives , while cis plus and trans plus give . Hence A is wrong (cis alkene with gives the racemate), B is right (2,3-dibromobutane, meso), C is right (butane-2,3-diol, meso), and D is wrong (trans alkene with gives racemic diol). Answer: B, C.
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