Chem 212 Alkyl Halide Problems 2

Chem 212 Alkyl Halide Problems 2

a)

Br

1. Provide the products, reagents or starting materials needed for the following reactions, show all stereochemistry. 2. Identify whether the reaction goes by an SN2 or an SN1 mechanism.

NaI acetone

Br

I)

I

I

NaI H2O

+

SN1

I

S N2 Br b)

c)

NaN3 DMSO

Br

H

OMs

d)

H2O

SN1

NaCN DMSO

SN2

j)

SN2

NaCN DMF

Br

SN2

N3

OH

H

NaBr acetone

CN

Br

k)

H I

SN2

NC H

SN1

NaBr H2O

l) Cl NaBr H2O

e) TsO

Br

SN1 Br

NaI H2O

m) Cl

f)

NaI acetone

Br

I

H OMs

SN2

SN1

I

H Br NaBr acetone

n) MsO H

Br H

H2O

g)

Br

OH

SN1

MeOH

o)

SN1

Br

NaBr H2O

h)

p)

SN1

OMe

TsO

NaH

OH

O

SN2

Br

OTs

3. Give the indicated rankings for the following. Provide explainations for your rankings e) Fastest SN1 reaction

a) Fastest SN2 reaction with NaI in acetone Br Br

Br

Br

fastest

NaI acetone

b) Fastest SN1 reaction with NaI in water

Br Br fastest

faster

Br

NaI water

faster

c) fastest SN2 reaction

slower

g) fastest reaction with NaSH

NaI Br acetone

I

faster

NaI Br hexane slower

I

Cl

Br

slowest

O

NaCN NaOH NaBr best about the same i) best nucleophile

OH best

NaI best

I fastest

h) best Nucleophile d) best solvent for a SN2 reaction

I

f) fastest SN1 reaction

Br slowest

Br

slower

slowest

Br

I

NaI water

NaBr

NaF worst

NaI water