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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