FUNCTIONAL GROUP

TRANSFORMATION USING SN2

REACTION

The SN2 Mechanism of

Nucleophilic Substitution

REACTION

CH3OH + Cl-

HO- + CH3Cl

MECHANISM
H H

H H

Cl
C

H-O:
H

The negative hydroxide ion

brings a pair of electrons to
the partially positive carbon
from the side with respect to
the leaving group. The chlorine
begins to move away with the
pairof electrons that bonded it
to the carbon.

H
H

Cl

In the transition state,

a bond between oxygen
and carbon is partially
formed and the bond
betweencarbon and chlorine
is partially broken. The
configuration of the carbon
atom begins to invert.

+ Cl-

C
H

Now the bond between

the oxygen and carbon
has formed and the chloride
ion has departed. The
configuration of the carbon
has inverted.

Stereochemistry of SN2 Reactions

Nucleophilic substitutions that exhibit
second-order kinetic behavior are
stereospecific and proceed with
inversion of configuration.

Inversion of Configuration

nucleophile attacks carbon

from side opposite bond
to the leaving group

three-dimensional
arrangement of bonds in
product is opposite to
that of reactant

 SN2 reaction are highly useful in organic

synthesis because they enable us to convert
one functional group in to another.
With the SN2 reaction, the functional group of
a methyl, primary, or secondary alkyl halide
can be transformed into that of an alcohol,
ether, thiol, thioether, nitrile, ester and so on.

OH-

FUNCTIONAL
GROUP
INTERCONVERSION

Alcohol

R OR'

Ether

R SH

Thiol

R SR'

Thioether

R C N

Nitrile

R'OSHR'SCN-

(-X-)

R OH

R-X

R'-C=C -

R = Me, 1o, or 2o
X= Cl, Br, or I

R C C R'

Alkyne

R'COO-

O
R O C R'

Ester

R'3N

+
R NR3' X-

N3 -

R-N3

Quaternary
ammonium halide

Alkyl azide

CH3Cl +
CH3CH2OH
Ethanol

Na OH
+

NaH

CH3OH + NaCl
CH3CH2O- Na+

+ H-H

Sodium propoxide
+ CH3I
CH3OCH2CH3 +
Ethyl methyl ether

Na+ I-

Synthesis of alkynes by elimination reaction

Mechanism for the E2 reaction
OCH3
H
H
C C
H H Br

The basic ethoxide ion

begins to remove a proton
from the karbon using its
electron pair to form a bond to it.
At the same time, the electron pair
of the C-H bond begins to move
in to become the bond of a double
bond, and thebromine begins to
depart with the electrons that bonded
it to the carbon

OCH3
H
H
C C
H H Br-

CH3
+
C C
OH
H
H
+ Br-

Partial bonds in the transition

state extend from the oxygen
atom that is removing the
hydrogen, through the carbon
skeleton of the developing
double bond, to the departing
leaving group. The flow of electron
density is from the base toward
the leaving group as an electron pair
fills the bonding orbital of the alkene

Synthesis of Alkynes by Elimination Reaction

1. Dehidrohalogenation of alkyl halides

base
heat
(-HX)

2. Dehydration of alcohols

OH

acid
heat

+ H2O

3. Hydrogenation of alkynes
R'

H2/Ni2B
syn addition
R

C
H

(Z)-Alkene

R'

Li or Na

NH3or NH2
anti addition

C
R'

(E)-Alkene