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Unformatted text preview: cis-2-butene is due to the specificity of formation and reaction of the bromonium ion: C=C CH 3 CH 3 H H Br Br ! + !" syn-addition C C Br + CH 3 CH 3 H H Br-(A) (B) Attack by bromide ion occurs by the equivalent paths A and B. (A) C C Br Br CH 3 CH 3 H H C C Br Br CH 3 CH 3 H H 2S,3S 2R,3R (B) A racemic form of the chiral diastereomer is produced . The mechanism does not allow formation of the meso-diastereomer from the cis-2-butene. This reaction is stereospecific . By a parallel mechanism, only the meso-diastereomer is formed in the bromination of trans-2-butene....
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