JEE Challenger
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Number of Stereoisomers from Bromination of trans-2-Butene

The number of stereoisomers obtained by bromination of trans\textit{trans}-2-butene is

Options

A

1

Correct
B

2

C

3

D

4

Step-by-Step Solution

Electrophilic addition of bromine (Br2\text{Br}_2) across an alkene proceeds via a cyclic bromonium ion intermediate, resulting in stereospecific anti-addition.

  • Anti-addition of Br2\text{Br}_2 to a trans-alkene yields a symmetric meso compound:
    trans-2-butene+Br2→anti-additionmeso-2,3-dibromobutane\textit{trans}\text{-2-butene} + \text{Br}_2 \xrightarrow{\text{anti-addition}} \textit{meso}\text{-2,3-dibromobutane}

  • The meso form possesses an internal plane of symmetry (and center of inversion in staggered conformation), making it achiral and superimposable on its mirror image.

  • Therefore, only 1 stereoisomer is obtained.

Correct Answer: A