Substitution vs Elimination.

SN2
H

Nu

Br

Br
H

Nu

substitution
Br
+ Nu

Substitution vs Elimination. (SN2 vs E2)

SN2
Nu

Br

Br
H

Nu

substitution
Br

Br
H

+ Nu
base

Nu

E2

Br

Nu H
elimination

SN 2
Br

Nu

Br
H

Nu

E2

Br

Br

H
Br

+ Nu
H

Nu

The product ratios

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

Nu H

Substitution vs Elimination. (SN1 vs E1)

Br

SN1

Nu

Nu
substitution

Substitution vs Elimination.
H
Br

SN1

Nu

Nu

E1

Br

Nu H
elimination

substitution

Br

SN1

Nu

E1

Nu

The product ratios of

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

Substitution vs Elimination. (SN2)

ethanol

+ Br

90%

10%

ethanol

+ Br

O
21%

+
79%

Substitution vs Elimination. (SN2)

ethanol

+ Br

25

9%

91%

ethanol

+ Br

O
25

21%

+
79%

Substitution vs Elimination. (SN2)

ethanol

+ Br

25

O
9%

+
91%

ethanol

+ Br
55

100%

Substitution vs Elimination. (SN2)

Br
15

+ CH3O

15

OCH3
99%

Br
15

15

1%

CH3

+ H3C CO
CH3

15

15

O
H3C C CH3

15% CH3

85%

Substitution vs Elimination. (SN2)

ethanol

+ Br

21%

79%

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 H3 X

C H2 X

SN2

mainly SN2
except with
hindered bases
eg. (CH3)3CO
when E2 is
observed.

CH X

2
mainly SN2 with
weak bases and
reactive nucleophiles (I,
RS, CN, etc).

NO SN2. In polar,
protic solvents SN1
and E1 reactions
are observed. High
temperature favors
E2 increases with elimination. When
strong bases.
the nucleophile is a
strong base, E2 is
SN1, E1 in
observed.
ionizing solvents.

How would you prepare methyl t-butylether?

C O C

CH3

C O

+ C X

CH3
O + Br C CH3
CH3

CH3 Br +

CH3
O C CH3
CH3

CH3

CH3
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.
H

Br

Br
Br
HO

HO

styrene