Substitution vs Elimination.

SN2
Br Nu Br
H H Nu H
substitution

Br
+ Nu
Substitution vs Elimination. (SN2 vs E2)

SN 2
Br Nu Br
H H Nu H
substitution

Br
Br Br E2
+ Nu
base
H H Nu H
Nu
elimination
 SN 2
Br Nu Br
H H Nu H

Br E2 Br Br

+ Nu
H Nu H
H Nu

The product ratios

of SN2 and E2
E reactions will depend
upon the nature of
the nucleophile and
base

R
Substitution vs Elimination. (SN1 vs E1)

SN1
Br Nu
Nu

substitution
Substitution vs Elimination.

H
SN1
Br Nu
Nu

substitution
Br
E1

Nu H

elimination
 H
SN 1
Br Nu
E1
Nu

The product ratios of

E SN1 and E1 reactions will
depend upon the nature
of the nucleophile

R
Substitution vs Elimination. (SN2)

ethanol
O +
O + Br
90% 10%

ethanol

O + Br O +
21% 79%
Substitution vs Elimination. (SN2)

ethanol

O + Br O +
25°
9% 91%

ethanol

O + Br O +
25° 21% 79%
Substitution vs Elimination. (SN2)

ethanol

O + Br O +
25°
9% 91%

ethanol

O + Br
55° 100%
Substitution vs Elimination. (SN2)

Br
15
+ CH3O 15 + 15
OCH3
99% 1%

CH3
Br
15
+ H3C CO 15 + 15
CH3 O
H3C C CH3 85%

15% CH3
Substitution vs Elimination. (SN2)

ethanol

O + Br O +
21% 79%

O
O
O
O + Br
+ Br
100%
How can I tell if the reaction
is SN2 or SN1 or E2 or E1?
Summary of SN2, SN1, E2 and E1 reactions.
R

R C X
R

R C H2 X R
C H3 X R CH X

1° 2° 3°

SN2 mainly SN2 mainly SN2 with

NO SN2. In polar,
except with weak bases and
protic solvents SN1
hindered bases reactive nuc-
leophiles (I, and E1 reactions
eg. (CH3)3CO are observed. High
RS, CN, etc).
when E2 is temperature favors
observed. E2 increases with elimination. When
strong bases. the nucleophile is a
SN1, E1 in strong base, E2 is
observed.
ionizing solvents.
How would you prepare methyl t-butylether?
C O C C O + C X
CH3
CH3 O + Br C CH3
CH3

? CH3
CH3
O C CH3
CH3

CH3
CH3 Br + O C CH3
CH3
Give an explanation for the following
observation. Methylchloromethylether is
reactive in both SN1 and SN2 reactions.

CH3 O CH2 Cl
Quiz 5: Using the general scheme shown below, propose two
syntheses of styrene. Identify which of these two would be
preferred.

O H

Br

Br
Br

HO
HO

styrene