NEET levelSingle correct optionDifficulty 1 of 3g3009
Optically active 3-bromo-3-methylhexane undergoes SN1 hydrolysis in aqueous acetone. The alcohol obtained is:
Aonly the inverted enantiomer
Bonly the enantiomer with retained configuration
Ca racemic mixture, because the planar carbocation is attacked from both faces
Dan optically active mixture with 90% inversion exactly
Answer: C
Ionisation gives a planar tertiary carbocation. Water attacks either face with equal probability, giving equal amounts of both enantiomers, so the product is racemic.