Number of Stereoisomers from Bromination of trans-2-Butene
The number of stereoisomers obtained by bromination of -2-butene is
Options
ACorrect
1
B
2
C
3
D
4
Topics & Concepts
Step-by-Step Solution
Electrophilic addition of bromine () across an alkene proceeds via a cyclic bromonium ion intermediate, resulting in stereospecific anti-addition.
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Anti-addition of to a trans-alkene yields a symmetric meso compound:
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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.
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Therefore, only 1 stereoisomer is obtained.
Correct Answer: A