FUNCTIONAL GROUP TRANSFORMATION

USING SN2 REACTION

 The SN2 Mechanism of
Nucleophilic Substitution
 REACTION HO- + CH3Cl CH3OH + Cl-
MECHANISM

H H H H H
-   H
H-O: C Cl H O C Cl H O C + Cl-

H H H

The negative hydroxide ion Now the bond between

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.
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.
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 three-dimensional

from side opposite bond arrangement of bonds in
to the leaving group product is opposite to
that of reactant
 Stereospecific Reaction
A stereospecific reaction is one in which
stereoisomeric starting materials give
stereoisomeric products.
The reaction of 2-bromooctane with
NaOH
(in ethanol-water) is stereospecific.
(+)-2-Bromooctane  (–)-2-
Octanol
(–)-2-Bromooctane  (+)-2-
Octanol
• 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-
R OH Alcohol

R'O-
Ether
FUNCTIONAL GROUP R OR'

INTERCONVERSION SH- Thiol

R SH

R'S-
R SR' Thioether

CN-
R C N Nitrile
(-X-)
R-X R'-C=C - R C C R' Alkyne

R = Me, 1o, or 2o R'COO- O

X= Cl, Br, or I R O C R' Ester

R'3N +
R NR3' X- Quaternary
ammonium halide
N3 -
R-N3 Alkyl azide
CH3Cl + Na OH CH3OH + NaCl

CH3CH2OH + NaH CH3CH2O- Na+ + H-H

Ethanol Sodium ethoxide

+ CH3I

CH3OCH2CH3 + Na+ I-

Ethyl methyl ether

 Exercises:
1. Starting with (S)-2-bromobutane, outline
syntheses of each of the following
compounds:
OC2H5
a. (R) c. (R)
O
b. (R)
O
SH
 Synthesis of alkynes by elimination reaction
• Mechanism for the E2 reaction

O-
O-
CH3
H CH3 H CH3
H H
C C H C C + OH
H H Br C C
H H Br- 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
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
C C C C
heat
(-HX)
H X

2. Dehydration of alcohols

acid + H2O
C C C C
heat
H OH
3. Hydrogenation of alkynes

R R'

H2/Ni2B C C
syn addition H H
(Z)-Alkene
R C C R'
R H
Li or Na
NH3or NH2 C C
anti addition H R'
(E)-Alkene