Practice Problems on SN1, SN2, E1 & E2 - Answers
[Pages:2]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
SN2
NaOH
Br H2O, heat
E2
Br
H2O
OH
SN1
I
CH3CH2O-Na+
E2
ethanol
NaSH
DMSO
SN2
HI
H SH
KOH
Br
DMSO
HO
SN2
NaNH2
E2
OTs
NH3
NH3
TsO
H2N
TsO
I
O
CH3
NaI
CH3
acetone
O
SN1
O
CH3
SN2
CH3
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
O
ethanol-water
CN
SN2
O
CH3OH / H2O
Br
+
OH
SN1
OCH3
Cl Cl
NaI (1 equiv.)
I
acetone
SN2
Cl
Br
CH3CH2OH
25oC
O
SN1
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
NaCN acetone
Br
HBr
SN2
CN
OH
SN1
Br
NH3
H
NH2
SN1
H
NaSH Br DMSO
SN2
SH
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