●

●
●
●
●

●
●
●
●
C6H5CH2SK , Δ
(1 eq.)
C6H5CH2SK , Δ
(1 eq.)
CN-
A
(1 eq.)
HBr
 RONa/∆

‒ ‒

‒ ‒
RONa/∆

α
+ +
Mechanism
Step 1

Step 2
+

+
Step 2
A part of the leaving group
attacks the front since it
is unable to get to the rear.
SOCl2
+ SO2 +
+ _
Cl
!
Step 1

Step 2

Step 3
Step 1

Step 3
+

+
+
-
+

+
 SOCl2
Ether

Solution

SOCl2
Ether
 SOCl2
Pyridine

Solution

SOCl2
Pyridine
Anchimeric assistance
β
 It consists essentially
of two SN2 substitutions.
 The neighbouring group acts
as a nucleophile, pushing out the
leaving group but still retaining
attachment to the molecule.
 +

..
+ Y‒
 ˉ

ˉ
 *

_ _
_ Cl * OH
*
:
+
:

*
..
..
..
..
 a

*
NaOH

+
* *
b a
_
OH b
*