Racemization during the SN1 reaction


What is shown here is the SN1 reaction of R-1-bromo-1-phenylethane in water.

First the bromide anion is leaving, and a flat intermediate is formed.
Subsequently, water molecules will attack this carbon cation, either from the opposite side, as shown on the left, or from the same side, shown below.

In these animations we end with the protonated alcohol. The final step, in which the proton is abstracted by some base in the reaction mixture, is omitted here.

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Check which product has the R, and which the S configuration.

If the bromide is not blocking the way, the two products will be formed with equal probability. A racemic mixture is the result.



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