NEET levelSingle correct optionDifficulty 1 of 3hx223
The optically active tertiary bromide shown is stirred with water in a polar protic medium and undergoes hydrolysis by the SN1 route. The alcohol obtained is:
AOptically inactive racemic mixture of two enantiomers
BA single enantiomer with inverted configuration
CA single enantiomer with retained configuration
DA meso compound
Answer: A
The tertiary bromide (3-bromo-3-methylhexane) ionises to a planar carbocation, which water attacks equally well from both faces. Both enantiomers of 3-methylhexan-3-ol form in equal amounts, giving an optically inactive racemic mixture.