The major product of the following reaction sequence is
(A)(see structure)✓ Correct
(B)(see structure)
(C)(see structure)
(D)(see structure)
Answer: (A)
Solution
The Grignard reagent (phenylmagnesium bromide) adds to the ketone carbonyl to form a tertiary alcohol. The acidic workup protonates the alkoxide. The product is a cyclic acetal/ketal structure where the tertiary alcohol carbon is incorporated into the ring system with the two oxygen atoms from the original diol protecting group.
JEE Advanced · 2016 · 22 May 2016 · Paper 2 · Single correct option