Date- 28-11-2020

Regd. Office : Aakash Tower, 8, Pusa Road, New Delhi-110005. Ph.: 011-47623456

REACTION OF THE DAY

Chemistry
Darzen’s Halogenation
Thionyl chloride (SOCl2) converts primary and secondary alcohols to alkyl chlorides.

Mechanism of the Darzen’s Halogenation

H Cl H
R – CH2– OH + Cl – S – Cl R–CH2–O–S R–CH2–O–S–Cl Py
+ +
O Cl O O

RCH2–O–S–Cl
O
Alkyl chlorosulfite

–
–Cl
Cl– + RCH2 – O – S – Cl RCH2Cl + O – S – Cl R–CH2Cl + SO2
O O
very good
leaving group

Important point:
 Reaction proceeds through SN2 reaction.

 Inversion of configuration takes place.

 In absence of pyridine, SNi mechanism would occur.

 

(1)
 Try Yourself

SOCl2/Py
(excess)
major product
1.
HO

(1) (2)
Cl
Cl Cl

(3) (4)
HO
Cl Cl
Cl



Answer of Question Based on Curtius Rearrangement

1. Answer (1)

(2)