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Organic Chemistry Introduction - Exam 3 with Solutions |, Exams of Organic Chemistry

Material Type: Exam; Class: Organic Chemistry 1 - Introduction; Subject: Chemistry; University: Oklahoma Baptist University; Term: Forever 1989;

Typology: Exams

2010/2011

Uploaded on 05/14/2011

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/
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.
Page
1
of
4
out
of
30
pf3
pf4

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Download Organic Chemistry Introduction - Exam 3 with Solutions | and more Exams Organic Chemistry in PDF only on Docsity!

/ 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 SN

reaction?

A. CH

13r B. CH

CI C. CH3F (!j)

,r

CH

  1. (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 ~~ ~(;<

  1. (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

C

B. Br2 C. CH 2

=CH

D. H2 ( E ~

  1. (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 SN

  1. (3f:>oints) vVhich reagent would be used to synthesize an alkyne from a vicinal dihalide?

A. (CH3)3CO- B. CH

Cl 2

C. HgS04 D. Li ® NH 2

8. (3 points) ZnC

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 oryridine E. water

  1. (3 points) vVhich reagent is most likely to be used in an E2 dehydration of a secondary

alcohol?

HCl A. CH 3

0- ~ H2S

C.

D.HI ~

If.

Page 1 of 4 out of 30

  1. (5 points).
  2. (5 point s).

~ 15. (5 points).

Br

DMSO

tI~c.

... 3 '

I'

P/1S 0

..

I

CHElVI3104 Exam 3

Give the major product, ideal reactant or opti-Inal reaction conditions for each

of the following reactions. Include stereochemistry in the consideration of yOUI'

answer.

  1. (5 poillts)

t

..

CH-sBr

  1. (5 points).

out of 25 Page 2 of 4

CHElVI 310 4

Exam 3

  1. (20 points) Propose a sy nthesis for the compound below, start.ing from I-bro mo- l

methylcyclohexanc. Indi cate t.he optimal reaction conditions for each st.e p of t.he re

act ion, and dr aw the major product of each step of t.he reaction.

JQ

out of 20 Pag e 4 of 4