Chem 212 Alkyl Halide Problems 5

Chem 212 Alkyl Halide Problems 5

ANSWERS

1. Rank the following carbocations in order of stability from worst to best. 1 3 a)

e) 3

1

2

3

1 H O

b) ~ same

f)

1

2

O

H

O

H

H

N 3

c)

2

1

g) 1

~ same 1

2 O

O

O

3

d)

h) 1

2

3

1

2

3

2. Provide the mechanisms for the following reactions. Clearly show every bond making and bond breaking step. Br

OH

OH ..

a)

H2O H O+

OH

I

f)

KOH H2O H

..

H2O H2O

b)

Br

g)

OH OH

Br H

H

..

H2O h)

EtOH Et

NaN3 H2O

N3

BuOH

H Br

..

N3

Cl

KOt Bu

d)

O

HOEt

..

Br t

H

H2O

..

c)

OEt

AgNO3 EtOH

KOt Bu t

Cl H

i)

BuOH

NaNH2

H

NH3

e)

Br

j)

SMe

NaSMe

Br

Br NaNH2

H

Br

NH3

3. Provide the products of the following reactions:

a)

Br

t

BuOH

NaNH2

d)

+

KOt Bu

NH3

I major

minor H2O

e) Br

b)

NaOMe MeOH

I

I c)

NaN3 DMF

Cl NR

f)

nearly racemic OH

KBr DMSO

Br