Page 252 - Mechanism and Theory in Organic Chemistry

Mechanisms Intermediate Between SN1 and SN2 241

-A

SOH + C-X
Q so-C / + X
+
H \\

I
Reaction coordinate Reaction coordinate
(a) (b)

\
SOH + C-X solvat4 \
4
r

Reaction coordinate
(c)
Figure 5.7 Single mechanism. (a) SN2. (b) Intermediate. (c) SN1.

rearrangements occurring during solvolysis of tosylates bearing substituted
phenyl groups on the /3-carbon (27) led them to suspect that nucleophilic assis-

C-C,
\ OTs
27