20.12.

2022

CHEM 106 WORKSHEET-6

1) Identify the mechanism when 1-bromobutane is treated with the following:

a) NaOH
b) NaSH
c) t-BuOK
d) NaOMe

2) Identify the mechanism when 2-bromopentane is treated with the following:

a) NaOEt
b) NaI/DMSO
c) t-BuOK
d) NaOMe

3) Identify the mechanism when 2-bromo-2-methylpentane is treated with the following:

a) EtOH
b) t-BuOK
c) NaOEt
d) NaOH

4) Which major product would you expect to obtain from each of the following reactions? In
each part give the mechanism (SN1, SN2, E1, or E2) by which the major product is formed.
a)
EtO-
Br
EtOH, 50 oC

b)

Br t-BuOK
t-BuOH, 50 oC

c)

MeO-
Br CH3OH, 50 oC

d)

t-BuOK
Br t-BuOH, 50 oC

e)

MeO-
3-Chloropentane
MeOH, 50 oC
f)

OH-
(R)-2-Bromobutane
25 oC

g)

25 oC
(S)-3-Bromo-3-methylhexane
MeOH

h)

I-
(S)-2-Bromooctane
MeOH, 50 oC

i)
OTs
NaSH
DMSO

j)
OTs
NaSH
MeOH

k)

t-BuOK
Br DMSO,

l)

NaCN
Br DMSO,

m)

Br H2O
5) Outline the mechanism showing all steps in its formation of following compounds when they
are subjected to acid-catalyzed dehydration.
a) b) c)
OH

OH
OH

6) The two stereoisomers of 1-bromo-1,2-dichloroethene cannot be designated as cis and trans

in the normal way because the double bond is trisubstituted. They can, however, be given (E)
and (Z) designations. Write a structural formula for each isomer and give each the proper
designation.

7)Starting with an appropiate alkyl halide and base, outline syntheses that would yield each of
the following alkenes as the major (or only product).
a) b) c)

8) Your goal is to synthesize 4,4-dimethyl-2-pentyne. You have a choice of beginning with

any of the following reagents. (Note: You also have sodium amide and liquid ammonia)
CH3 CH3
H3C C CH H3C C Br H3C C C CH H3C I
CH3 CH3

9) Synthesize propyne from each of the following:

a) CH3CHBrCH2Br
b) CH3CH=CH2