Which of the following has highly acidic hydrogen?
- [figure]
- [figure]
- [figure]
- [figure]
Answer
(4) [figure]
Solution
Most acidic H = α-H whose carbanion is best stabilised by resonance.
(D): CH2 lies between two C=O groups (active methylene):
CH3- O \|C- CH- O \|C-CH2-CH3
∵ the negative charge is delocalised onto both O atoms ⇒ most stable conjugate base
(A), (B), (C): every α-H is next to only one C=O ⇒ less stable carbanion
Answer: (4)