The ascending order of relative rate of solvolysis of following compounds is : [figure]
- (C) < (D) < (B) < (A)
- (D) < (A) < (B) < (C)
- (D) < (B) < (A) < (C)
- (C) < (B) < (A) < (D)
Answer
(2) (D) < (A) < (B) < (C)
Solution
Solvolysis is SN1: faster the more stable the carbocation formed.
(D) secondary alkyl: hyperconjugation only:
[figure]
(A) tertiary: 3 alkyl groups, hyperconjugation + I effect:
[figure]
(B) secondary benzylic: resonance with one ring:
[figure]
(C) diphenylmethyl: resonance with two rings:
[figure]
Resonance (aryl) > hyperconjugation; two rings > one ring
∴ rate: (D) < (A) < (B) < (C)
Answer: (2)