The hydrolysis of optically active 2-bromobutane leads to the formation of (±)-butan-2-ol, illustrating racemisation with a mixture of products having the same and opposite configurations.
Provide an example of racemisation in the hydrolysis of an optically active alkyl halide and the resulting product.
Share
Consider the hydrolysis of (R)-2-bromobutane, an optically active alkyl halide, through SN1 mechanism. The bromine departs, forming a planar, achiral carbocation intermediate. Water then attacks the carbocation from either face with equal probability. Consequently, a racemic mixture of (R)-2-butanol and (S)-2-butanol is obtained. The hydrolysis results in racemisation, as the stereochemistry of the chiral center is lost during the formation of the carbocation intermediate, leading to the production of both enantiomers. This illustrates how the SN1 mechanism in hydrolysis can contribute to the racemization of optically active alkyl halides.