Practice Problems on SN1, SN2, E1 & E2 - Answers

1. Describe the following chemical reactions as SN1, SN2, E1 & E2. Draw a curved
arrow mechanism for each reaction.
KCN
Cl DMSO CN S N2

NaOH
Br
E2
H2O, heat

Br H2O OH
S N1

I
CH3CH2O-Na+
E2
ethanol

NaSH
DMSO S N2

H I H SH

KOH
Br HO S N2
DMSO

NaNH2
E2
OTs NH3

NH3
S N1

TsO H 2N

TsO
I
O CH 3
NaI O CH 3
CH 3 acetone S N2
O CH 3
O
 2. For each of the chemical substitution reactions below identify the major products
and whether the reaction is likely an SN1 or SN2.

Br NaCN CN S N2
O O
ethanol-water

CH3OH / H2O + S N1
Br OH OCH3

Cl NaI (1 equiv.) I
S N2
acetone

Cl Cl

Br O
CH3CH2OH S N1
25oC

3. For each of the following compounds provide appropriate reactants and solvent
systems to synthesize them by a substitution reaction. Show which type of
substitution: SN1 or SN2.

Br NH 2
Br
NH3 S N1
NaCN S N2
acetone CN

H H

Br OH
HBr
S N1
NaSH S N2
Br DMSO SH