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Instructions
This exam will be closed book. No notes, books,
calculators, or molecular models will be allowed.
The exam will be comprised of two distinct parts:
Part I will consist of a series of multiple choice
questions. Your answers to these questions must be
submitted on a Scantron bubble sheet. The answer
sheet will be provided for you, but you will need
your own #2 pencil(s). Only answers marked on the
bubble sheet will be graded. Answers to Part I
questions marked on the exam itself cannot not be
graded. No re-grades will be possible on Part I of the
exam.
Part II consists of questions for which you will need
to write out your answers, using structures and/or
words. This part of the exam will be hand-graded.
Answers for the Part II questions that are written in
pencil will not be eligible for re-grades. Answers
written in pencil with ink overlay will not be eligible
for re-grades. If you use a pen to answer the Part II
questions, only blue or black ink is acceptable.
Answers written in red ink cannot be graded.
1. You must have your valid UT ID card (or
other government-issued ID) with you. You
will need to show it to the proctors when
you turn in your exam.
2. Chapter 4 of the Universitys General
Information catalog outlines this
universitys policies regarding exams, as
well as other quizzes administered during
the semester. Specifically, students are
expected to remain in the exam room until a
test is completed. These policies will be
strictly enforced, with no exceptions. You
may not leave the room for any reason until
you are ready to turn in your exam. If you
wish to leave the room, you will need to turn
in your exam to the proctors, and you will
not be allowed to return. Please, plan
accordingly by using the rest room before
the exam starts.

CH 310/318 M
Exam 2 v 1.0

Question
1
2
3
4
5
Section II

Value
24
10
20
11
10
75

Section I
Raw Total

75
150

Grade

Score

UTID: ________________________

October 2010

CH310/318M-Exam 2 VERSION 1
Objective Test Section
Identify the choice that best completes the statement or answers the question. There is only one correct answer; please
carefully bubble your choice on the scantron sheet. (3pts. ea; 75 pts this section)
1. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

1
2
3
4

2. Which of the following alkenes is most likely to undergo rearrangement upon acid-catalyzed hydration (treatment
with aqueous H2SO4)?

a.
b.
c.
d.

1
2
3
4

3. What is the IUPAC name of the following compound?

a.
b.
c.
d.

(E)-3-methyl-3-pentene
(Z)-3-methyl-3-pentene
(E)-3-methyl-2-pentene
(Z)-3-methyl-2-pentene

4. What is the index of hydrogen deficiency of a compound with a molecular formula of C 6H8?
a. 0
b. 1
c. 2
d. 3
5. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

1
2
3
4

6. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

1
2
3
4

7. What is (are) the major organic product(s) obtained from the following reaction?

1.
2.
3.
a.
b.
c.
d.

(2R,3R)-dibromobutane
(2S,3S)-dibromobutane
meso-2,3-dibromobutane
only 1
only 2
only 3
only 1 and 2

8. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

1
2
3
4

9. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

1
2
3
4

10. Which atom in the following structure is preferentially protonated by a strong acid?

a.
b.
c.
d.

i
ii
iii
iv

11. What is (are) the major organic product(s) obtained from the following reaction?

a.
b.
c.
d.

only 1
only 2
only 3
only 2 and 3

12. Which of the following terms describes the role of ethanol in the acid-base reaction shown?

a.
b.
c.
d.

Brnsted-Lowry acid
Brnsted-Lowry base
Lewis acid
Lewis base

13. What is the correct order of stability of the following carbocations (more stable > less stable)?

a.
b.
c.
d.

1>2>3
1>3>2
3>1>2
3>2>1

14. What is the IUPAC name of the following compound?

a.
b.
c.
d.

2-methylenepentane
2-methyl-1-pentene
2-vinylpentane
2-propyl-1-propene

15. What is the best choice of reagent to perform the following transformation?

a.
b.
c.
d.

Br2
HBr
Br2, H2O
N-bromosuccinimide

16. What type of reactive intermediate is formed in the reaction of an alkene with Br2 and water to give a
bromohydrin?
a. carbocation
b. carbanion
c. radical
d. cyclic bromonium ion
17. Which of the following terms describes the role of ethene in the acid-base reaction shown?

a.
b.
c.
d.

Brnsted-Lowry acid
Brnsted-Lowry base
Lewis acid
Lewis base

18. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

1
2
3
4

19. Which of the following energy diagrams best represents the changes in energy during addition of HBr to an
alkene?

a.
b.
c.
d.

1
2
3
4

20. What is the best choice of reagent(s) to perform the following transformation?

a.
b.
c.
d.

H2O, H2SO4
Hg(OAc)2 and H2O ; followed by NaBH4
B2H6; followed by H2O2, NaOH
OsO4; followed by NaHSO3

21. Which set of curved arrows accounts for the deprotonation of an acid (A-H) by a base (:B)?

a.
b.
c.
d.

1
2
3
4

22. What type of carbocation is shown?

a.
b.
c.
d.

primary
secondary
tertiary
quaternary

23. Which species is the conjugate acid in the following acid-base reaction?

a.
b.
c.
d.

1
2
3
4

24. Approximately how long is a carbon-carbon triple bond of an alkyne?


a. 110 pm
b. 121 pm
c. 135 pm
d. 156 pm
25. What is the major organic product obtained from the following reaction?

a.
b.
c.
d.

1
2
3
4

ID: A

CH310/318M-Exam 2 VERSION 1
Answer Section
MULTIPLE CHOICE
1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
12.
13.
14.
15.
16.
17.
18.
19.
20.
21.
22.
23.
24.
25.

ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:
ANS:

B
B
D
D
B
B
C
D
C
A
A
A
D
B
C
D
B
B
A
C
B
B
D
B
B

PTS:
PTS:
PTS:
PTS:
PTS:
PTS:
PTS:
PTS:
PTS:
PTS:
PTS:
PTS:
PTS:
PTS:
PTS:
PTS:
PTS:
PTS:
PTS:
PTS:
PTS:
PTS:
PTS:
PTS:
PTS:

3
3
3
3
3
3
3
3
3
3
3
3
3
3
3
3
3
3
3
3
3
3
3
3
3

UTEID

CH 310/318 M EXAM #2 v 1.0


PART 2:

Free Style Answer Format

KEY

(75 pts in this section)

1) Provide the reagents and steps for each of the following transformations. For credit, your
reactions must be stereo and regiospecific when necessary. Note, that there may be more
than one method to achieve the product, but you need only provide one. (24 pts)

CH3
Br
CH3

Br
OH
H

CH3

H
Br2; CH2Cl2

1) Hg(OAc)2
2) NaBH4

OH

OR
H2SO4 (aq)

CH3
Br

HBr but NOT


aqueous

H
CH3

1) BH3
2) H2O2; NaOH

HCl but NOT


aqueous
Br2; H2O
CH3
Cl

CH3
OH

H
Br
H

UTEID

CH 310/318 M EXAM #2 v 1.0

KEY

2) One of the advantages of developing different reagents for organic synthesis, is the ability to
control the products. 3,3-dimethyl-1-butene can be converted into 2 different products by the
reagents below. Draw the products, and indicate any regiochemistry. (10 pts)

3) 1,3-butadiene will undergo addition reactions with HBr to form 2 products. Follow the
instructions for the mechanism and predict the structure of these two products. (Hint: the
carbocation is stabilized by resonance.) (20 pts)

H
H

Br
H

H
H

H
Form the carbocation

Br

Br

Show the 2 resonance


structures

H
H

H
Br

H
Br

Show the 2products, which result from the attack of Bromide

UTEID

CH 310/318 M EXAM #2 v 1.0

KEY

4) Mechanism The experimental evidence for the bromonium ion, is the stereochemistry of the
products. For the bromination of E-stilbene, show the mechanism and label the
stereochemistry of the product. Chiral centers are produced, so assign the R & S designation
to the chiral carbons. (11 pts)

UTEID

CH 310/318 M EXAM #2 v 1.0

KEY

5) Reactions. Provide the products of the following reactions. For full credit, show stereo and
regiochemistry where necessary. (10 pts)

OH
H2C

OH

1) OsO4
2) NaHSO3

H
CH3

CH3
H2
Pt or Pd or Ni

CH2CH3

CH2CH3
H

END OF EXAM