Explain the stereiochemical consequences of SN1 reaction by taking 2-bromobutane as an example?

1 Answer
anor277
Feb 8, 2018

Loss of any existing chirality....

Explanation:

Suppose we start with homochiral #H_3C-stackrel"*"CHBrCH_2CH_3#...the starred carbon is chiral....and a bond-breaking mechanism, which proceeds by a three-coordinate carbocation CANNOT support or transfer the chirality.

And thus hydrolysis (for instance) would lead to a racemic secondary alcohol....#H_3C-CH(OH)CH_2CH_3#.

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