/
CHEM
3104
Exam
3
Name:
@
___
~
___
_
This
exam
contains
100
points
from 20
questions
on
4 pages.
Circle
the
best
answer
to
each
question
below.
1.
(3
points)
vVhich
one
of
the
following cornpoLlnds will
most
readily
undergo
an
SN2
reaction?
A.
CH
3
13r
B.
CH
3CI C.
CH3F
(!j)
,r
CH31
2.
(3
points)
vVhich
one
~
0
the
following
compounds
"vould
be
the
best
nucleophile in
methanol?
r,.
I.
I"j
f'o
/
--
3.
(3
points)
'I\1hich
type
of
reaction
do
acetylide
ions
undergo
with
alkyl halides?
A.
El
@E2
C.
SNI
~
~
~(;<
4.
(3
points)
Which
one
of
the
~
lI
,()
wing
compounds
is a
protic
solvent?
A.
DMF
B.
DMSO
(§j
acetic
acid
D.
acetonitrile
E.
dichloromethane
5.
(3
points)
Which
one
of
the
following
reagents
would
be
used
ill a
'Villiamson
ether
synthesis?
a
(CH
3
)3
C1
B. Br2 C.
CH
2
=CH
2 D.
H2
(
E
~
6.
(3
oi
81.
High
temperatures
tend
to
favor
which
s
~
ctionS?
'
A
~
E / d
E2
B.
El
and
SNI
0 E2
and
SN2 D.
SNI
and
SN2
7.
(3f:>oints) vVhich
reagent
would
be
used
to
synthesize
an
alkyne
from a vicinal dihalide?
A.
(CH3)3CO-
B.
CH
2
Cl
2 C.
HgS04
D. Li ®
NH
2
8.
(3
points)
ZnC12 would
be
used
to
synthesize
an
alkyl
chloride from
oa
primary
alcohol
B. a
primary
alkyl
iodide
C. a
terminal
alkene
D. a
tertiary
alcohol
E.
a
tertiary
alkyl
iodide
9.
(3
points)
vVhat
compound
is
usually
used
as
the
solvent
in
the
formation
of a
sulfonate
ester?
~
"\
A. DNISO B.
THF
C.
ethanol
or
yridine
E.
water
10. (3
points)
vVhich
reagent
is
most
likely
to
be
used
in
an
E2
dehydration
of
a
secondary
alcohol?
HCl
A.
CH
3
0-
~
H2S04
C.
D.HI
~
If.
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out
of
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