Practice Problems on SN1, SN2, E1 & E2
1. Describe the following chemical reactions as SN1, SN2, E1 & E2. Draw a curved
arrow mechanism for each reaction.
KCN
DMSO
Cl
CN
NaOH
H2O, heat
Br
Br
OH
H2O
I
CH3CH2O-Na+
ethanol
NaSH
DMSO
H
H
I
KOH
DMSO
Br
SH
HO
NaNH2
NH3
OTs
NH3
TsO
H 2N
TsO
I
CH 3
O
CH 3
NaI
acetone
CH 3
O
CH 3
O
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
O
NaCN
ethanol-water
CH3OH / H2O
Br
NaI (1 equiv.)
acetone
Cl
Cl
Br
CH3CH2OH
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.
H2N
CN
H
Br
SH
Prepared by José Laboy