Question

1. Propose a mechanism for the following reactions: Ho - t enantiomer hº W + TEH x + H20 = OH OH

Answer 1

This is an example of acid catalysed hydration of an alkene. This reaction proceeds via formation of secondary carbocation which is planar in shape and hence can be attacked from both sides of plane and resulting in formation of 50:50 mixture of enantiomers (a and b here).

Mechanism . 120, H2SO4 ~ I First step Ho Thuson 2 Hotnson 449-M ) - -ne thy 2°Сas bocation" (planarė) :03 attack can happen from both sides of plane a on enantiomelb? ni ning ot / m3 0 to anunt H. enantiomere