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Practice Problems on SN1, SN2, E1 & E2 - Answers, Exams of Chemistry

Practice Questions on SN1, SN2, E1 & E2 with Answers.

Typology: Exams

2018/2019

Uploaded on 02/11/2022

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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.
Cl
KCN
DMSO CN
Br
NaOH
H2O, heat
Br H2OOH
I
CH3CH2O-Na+
ethanol
I
H
NaSH
DMSO
SH
H
Br HO
KOH
DMSO
OTs
NaNH2
NH3
TsO
NH3
H2N
O
O
CH3
CH3
TsO
NaI
acetone
O
O
CH3
CH3
I
SN2
E2
SN
1
SN2
E2
SN2
E2
SN
1
SN2
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Practice Problems on SN1, SN2, E 1 & E 2 - Answers

1. Describe the following chemical reactions as SN1, SN2, E 1 & E 2. Draw a curved

arrow mechanism for each reaction.

Cl

KCN

DMSO CN

Br

NaOH

H 2 O, heat

Br H 2 O OH

I

CH 3 CH 2 O-Na+

ethanol

H I

NaSH

DMSO

H SH

Br HO

KOH

DMSO

OTs

NaNH 2

NH 3

TsO

NH 3

H 2 N

O

O

CH 3

CH 3

TsO

NaI

acetone

O

O

CH 3

CH 3

I

SN 2

E

SN 1

SN 2

E

SN 2

E

SN 1

SN 2

2. For each of the chemical substitution reactions below identify the major products

and whether the reaction is likely an SN1 or SN2.

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.

O

Br NaCN

ethanol-water

Br

CH 3 OH / H 2 O

Cl

Cl NaI (1 equiv.)

acetone

Br

CH 3 CH 2 OH

25 oC

O

CN SN 2

OH

Cl

I

SN 2

O

SN 1

CN

OH

Br

SN 2

Br

NaCN

acetone

HBr

SN 1

NH 2 H Br H

NH 3 SN 1

Br SH NaSH DMSO

SN 2

OCH 3

+ SN 1