Consider the solvolysis of -chloro-3-methylhexane in an excess of pure water. Predicting the stereochemical nature of the major synthesized product reveals it to be:

Question

Consider the solvolysis of $(S)-3$ -chloro-3-methylhexane in an excess of pure water. Predicting the stereochemical nature of the major synthesized product reveals it to be:

Prashant Kotian · Accepted Answer

Correct answer: C. 3-chloro-3-methylhexane is a tertiary alkyl halide. When solvolyzed in water (a polar protic solvent), it strictly undergoes an mechanism. The chloride leaving group departs to form a planar carbocation. Water molecules subsequently attack this planar intermediate from both faces with roughly equal probability. As a result, the initially pure -enantiomer is converted into an equimolar racemic mixture of - and -methylhexan-3-ol.

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