SN2

Br H

Nu H

Br
Nu H

substitution

Br
+ Nu

SN2

Br H

Nu H

Br
Nu H

substitution

Br + Nu base

Br

E2

Br

Nu

Nu H
elimination

SN2
Br H
Br + Nu H
H Nu

major product
Nu H Br
Nu
Br

E2

Br

Nu H

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

SN2
Br H
Br + Nu H
H Nu

Nu H

Br
Nu
Br

E2

Br

Nu H

major product

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

Substitution vs Elimination. (SN1 vs E1)

SN1
Nu

Br

Nu

substitution

Substitution vs Elimination. (SN1 vs E1)

H
Br

SN1
Nu

Nu

E1

Br

substitution

Nu H
elimination

Br

SN1 E1

H
Nu Nu

The overall rate of the reaction is independent of the nucleophile.

G

The product ratios of SN1 and E1 reactions will depend upon the nature of the nucleophile

Substitution vs Elimination. (SN2)

ethanol

+ Br

O 90%

+
10%

ethanol

+ Br

O 21%

+
79%

Substitution vs Elimination. (SN2)

ethanol

+ Br

25

O 9%

+
91%

ethanol

+ Br
25

O 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

15

99%

1%

CH3 Br
15

+ H3C CO
CH3

15

+
O

15

H3C C CH3

85%

15% CH3

Review: Substitution vs Elimination. (SN2 vs E2) SN2

Nu H

Br
Nu H
substitution

Br + Nu H

steric effects temperature

Br

E2

Br

Nu

Nu H
elimination

Substitution vs Elimination. (SN2)

ethanol

+ Br

O 21%
O

+
79%

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 R C R X

C H3 X

C H2 X

CH X

SN2

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

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

polar, protic solvents SN1 and E1 reactions are observed. High temperature favors E2 increases with elimination. When strong bases. the nucleophile is a SN1, E1 in strong base, E2 is ionizing solvents. observed.

NO SN2. In

How would you prepare methyl t-butylether?

C O C C O

+ C X

CH3

CH3 O + Br C CH3 CH3

?
CH3 O C CH3 CH3

CH3

CH3 O C CH3 CH3

CH3 Br +

Summary of SN2, SN1, E2 and E1 reactions.

R R R C R X

C H3 X

C H2 X

CH X

SN2

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

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

polar, protic solvents SN1 and E1 reactions are observed. High temperature favors E2 increases with elimination. When strong bases. the nucleophile is a SN1, E1 in strong base, E2 is ionizing solvents. observed.

NO SN2. In

How would you prepare methyl t-butylether?

C O C C O

+ C X

CH3

H2C H CH3 O + Br C CH3 3 CH3 3

CH2 C H3C CH3

CH3 O C CH3 CH3

CH3

CH3 Br +

CH3 O C CH3 CH3

Quiz 6-2: Using the general scheme shown below, propose two syntheses of styrene. Identify which of these two would be preferred.

OH

H Br

HO

Br
Br

HO

HO

styrene

Quiz 6-3. Give an explanation for the following observation. Methylchloromethylether is reactive in both SN1 and SN2 reactions.
H N C CH3 C O H S N2
C N CH3 O CH2 C N + Cl

Cl

CH3 O CH2 Cl

SN1

CH3

CH2

CH3

CH2

6-4. Predict the major product of the following reaction.

Br Br + HO

C4H8O

HO

OH

C4H10O2

6-4. Predict the major product of the following reaction.

Br Br + HO

C4H8O

Br + Br

6-4. Predict the major product of the following reaction.

Br Br + HO

C4H8O
+ Br O

Br + Br

Br

6-4. Predict the major product of the following reaction.

Br Br + HO

6-5. Predict the major product of the following reaction.

S Br + H O

O S O S

major product
S H O