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Unformatted text preview: The 1,2-dibromo compound is more interesting. An open cation can t be involved, as shown above, because it must lead to both - and -1,2-dibromocyclopentane, and the trans compound must be optically active if this mechanism is operative. Presumably what happens is that this open cation is captured immediately on formation to give a meso bromonium ion. Now there can be no cis dibromide formed, and the trans 1,2-dibromide must be racemic. Br Br H H Br a b b a Br H H Br Br H H Br a racemic mixture meso S N 2...
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- Fall '10