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