Cl
(CH 2 ) 3 CH(CH 3 ) 2
H 3 CC^2 H^5
HCl
H 2 O +
C 2 H 5 OH
60% S
(inversion)
40% R
(retention)
(R)-6-Chloro-
2,6-dimethyloctane
HO +
(CH 2 ) 3 CH(CH 3 ) 2
C 2 H 5
OH CH^3
(CH 2 ) 3 CH(CH 3 ) 2
H 3 CC^2 H^5
CBr
A
BD
H 2 O
H 2 O
This side shielded
from attack
This side open to
attack
Ion pair Free carbocation
+
Inversion Racemization
Br^ −
C Br^ −
BD
A
+ C
BD
A
+
COH
A
BD
HO C
A
DB
HO C
A
DB
H 2 O H 2 O
6.13B SOLVOLYSIS
- Solvolysis is a nucleophilic substitution in which the nucleophile is a molecule
of the solvent (solvent + lysis: cleavage by the solvent).
- Hydrolysis: when the solvent is water.
- Alcoholysis: when the solvent is an alcohol (e.g. methanolysis).
Examples of Solvolysis
(H 3 C) 3 C Br + H 2 O (H 3 C) 3 C OH + HBr
(H 3 C) 3 C Cl + CH 3 OH (H 3 C) 3 C OCH 3 + HCl
(H 3 C) 3 C Cl + (H 3 C) 3 C OCH H
O
HCOH
O
+ Cl
- Solvolysis involves the initial formation of a carbocation and the subsequent
reaction of that cation with a molecule of the solvent:
