3.

SNi & SN2Ar

Nucleophilic Substitution

Reaction Mechanisms 4

Anupam Gupta
Anupam Gupta
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SNi & SN2Ar

Nucleophilic Substitution

Reaction Mechanisms 4

Anupam Gupta
 Reaction Mechanism

Nucleophilic substitution reaction:

Elimination reactions: Addition reactions:

● SN2 ● E1 ● Nucleophilic Addition to

● SN1 ● E2 carbonyls

● SNi ● E1cB ● Electrophilic Addition to

● SN2Ar ● Ei pi-bonds

● SN2Th
● Benzyne Mechanism

Electrophilic Substitution reactions

● EAS
 SNi Mechanism

The reaction proceed by SNi Mechanism (Internal nucleophilic substitution) and

involves retention of configuration at chiral centre.
 Reaction with SOCl2 (In absence of base)

This reaction of Thionyl Chloride is known as Darzens Halogenation.

 H OH
C
CH3(CH2)4CH2 CH3

H O
..
CH3 C - ..OH + Cl - S - Cl

H5C2
SNi Mechanism
Reaction with Phosgene COCl2
 Reaction with SOCl2 (in presence of base)

In presence of base such as pyridine the reaction proceeds by SN2 mechanism

and involve inversion of configuration at the substrate center
 H O
..
CH3 C - ..OH + Cl - S - Cl + Py

H5C2
 H OH
SOCl2
C
CH3(CH2)4CH2 CH3 Py
 CH3
SOCl2
H OH
Py

C2H5
Product of the above reaction is

A. B. C. D.
Consider the following reaction

In the above reaction phenomenon will take place:

A. Inversion
B. Retention
C. Racemisation
D. isomerisation
 SN2Ar

This is the characteristic reaction of aryl halides with ortho or para electron withdrawing
substituent.
 SN2Ar

Normally reaction possible only at high temperature and pressure

Cl

OH-
 SN2Ar

Cl

OH-

Hot

NO2

Cl
NO2
OH-
Warm

NO2
SN2Ar Mechanism
Give the products in following reaction

A. B.
Give the products in following reaction

C. D.
Factors affecting rate of SN2Ar
 Cl
O2N NO2
OH-

NO2
Write the correct reactivity order with NaOH for the following compounds.
Which of the following reaction is SN2Ar reaction ?

A. B.

C. D.
Which of the following compound gives fastest SN2 Ar reaction ?

A. B. C. D.
Above reaction has maximum rate when:

A. Y = -I
B. Y = - Br
C. Y = -Cl
D. Y = -F
HO OH
SOCl2
Product is :
Pyridine

Cl
HO
Cl Cl
A. B.

Cl Cl Cl
HO
C. D.
 Product, Identify the product

A. B.

C. D.
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