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 2 1
3 1 2

b) H
f) O O O
~ same 1 H H H

N
3 2 1
c)

g)
1 ~ same
2 1 3
O O O

d) h)

2 1 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
I OH
f)
KOH
H H2O
O+
H ..
H2O

g) Br OEt
H2O OH AgNO3
b) EtOH
H ..
Br OH .. O EtOH
H H HOEt Et
..
H2O
..
H2O
c) Cl N3
Br h)
KOt Bu NaN3
H2O N3
t
BuOH
H

d) Br
KOt Bu Cl
t BuOH i) H
NaNH2
H
NH3

e) Br SMe j) Br Br
NaSMe NaNH2
Br NH3
H

3. Provide the products of the following reactions:

d) NaNH2
Br +
a) KOt Bu NH3
I
t BuOH major minor

e) H2O
nearly
b) Br racemic
NaOMe
MeOH I OH

I
Cl KBr Br
c) NaN3 f) DMSO
NR
DMF