The aldehydes which will not form Grignard product with one equivalent Grignard reagents are:abcd
(A)(b), (d)✓ Correct
(B)(b), (c)
(C)(b), (c), (d)
(D)(c), (d)
Answer: (A)
Solution
A Grignard reagent is destroyed by any acidic proton before it can add to a carbonyl. The aldehyde carrying a −COOH group and the one carrying a −CHX2OH group each have such an acidic hydrogen, so a single equivalent of the reagent is used up in simple protonation rather than addition. These two therefore do not give the expected Grignard addition product.
JEE Main · 2019 · 12 Jan 2019 · Shift 2 · Single correct option