The ascending acidity order of the following H atoms is [figure]
- A < B < D < C
- A < B < C < D
- D < C < B < A
- C < D < B < A
Answer
(4) C < D < B < A
Solution
Acidity of C–H ∝ stability of the carbanion left after losing H+.
A: H on sp carbon (50% s) ⇒ HC C most stable ⇒ most acidic
B: H on sp² carbon (33% s) ⇒ H2C=CH next
D: H on sp³ 1° carbon ⇒ CH3CH2 (one +I group)
C: H on sp³ 3° carbon ⇒ (CH3)3C destabilised by three +I CH3 ⇒ least acidic
∴ C < D < B < A
Answer: (4)