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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 1

Question
1
2
3
4
5
6
Section II

Value
16
13
12
10
14
10
75

Section I
Raw Total

75
150

Grade

Score

UTID: ________________________

September 2010

CH310/318M-Exam I v2.0
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. Which of the following structures have a plane of symmetry?

a.
b.
c.
d.

only 1 and 2
only 2 and 4
only 3 and 4
1, 2, 3 and 4

2. Which of the following Newman projections represents meso-2,3-dibromobutane?

a.
b.
c.
d.

1
2
3
4

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

a.
b.
c.
d.

trans-1-tert-butyl-2-methylcyclopentane
cis-1-tert-butyl-2-methylcyclopentane
trans-1-isopropyl-4-methylcyclopentane
cis-1-isopropyl-2-methylcyclopentane

4. Which of the following Newman projections represents the most stable conformation of 2,3-dimethylbutane?

a.
b.
c.
d.

1
2
3
4

5. Which of the following structures represent the same stereoisomer?

a.
b.
c.
d.

only 1 and 2
only 1 and 3
only 2 and 3
1, 2 and 3

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

a.
b.
c.
d.

isooctane
3-propylpentane
3-ethylhexane
1,1-diethylpropane

7. Which of the following compounds is/are chiral?

a.
b.
c.
d.

only 1
only 1 and 2
only 2 and 3
1, 2 and 3

8. How many hydrogen atoms are there in dodecane, the linear hydrocarbon with twelve carbon atoms?
a. 20
b. 26
c. 12
d. 24
9. Which of the following is the definition of chirality?
a. The non-superposability of an object on its mirror image
b. A molecule with a mirror image
c. A molecule that has a carbon atom with four different substituents
d. The superposability of an object on its mirror image
10. How many hydrogen atoms are there in nonane, the linear hydrocarbon with nine carbon atoms?
a. 18
b. 22
c. 20
d. 16
11. What is the IUPAC name of the following compound?

a.
b.
c.
d.

2-isopropyl-5-methylpentane
5-isopropyl-2-methylpentane
2,3,5-trimethylhexane
1,2-diisopropylpropane

12. Which of the following compounds has 1, 2, 3 and 4 carbon atoms?

a. 2,2,3-trimethylhexane
b. hexane
c. 2,2-dimethylhexane
d. 2-methylhexane

13. Which of the following cycloalkanes has the most ring strain?
a. cyclobutane
b. cyclohexane
c. cyclopropane
d. cyclopentane
14. Which of the following statements is true?
a. Superposable structural isomers are enantiomers
b. All molecules that have stereocenter centers are chiral
c. Isomers that are not superposable on their mirror images are enantiomers
d. All mirror images are enantiomers
15. What is the approximate CCC bond angle in propane?
a. 120
b. 180
c. 90
d. 109
16. Which of the following anions is the strongest base?
a. NH2
b. Cl
c. HO
d. CH3COO
17. Which of the following statements regarding optical rotation is not true?
a. All R enantiomers are dextrorotatory.
b. All () enantiomers rotate plane-polarized light in a counterclockwise direction.
c. All (+) enantiomers are dextrorotatory.
d. All (+) and () enantiomers rotate plane-polarized light in opposite directions.
18. Which of the following alkanes has the highest boiling point?
a. pentane
b. propane
c. hexane
d. butane
19. Which of the following is the definition of a meso compound?
a. A molecule with stereocenter centers which is not chiral
b. A chiral compound with more than one stereocenter center
c. A diastereomer with no stereocenter centers
d. A molecule with stereocenter centers which is chiral
20. What is the approximate dihedral angle between the two chlorine atoms in the diequatorial conformation of
trans-1,2-dichlorocyclohexane?
a. 0
b. 180
c. 60
d. 120

21. Which of the following is the correct order of decreasing basicity (stronger base > weaker base)?
a. CH3COONa > NaOH > NaOMe > NaNMe2
b. MeNH2 > NH3 > MeOH > CH4
c. NH3 > Me3N > H2O > MeOH
d. NH3 > MeNH2 > H2O > HF
22. Which of the following have the R configuration?

a.
b.
c.
d.

only 1
only 2
only 1 and 2
1, 2 and 3

23. Which of the following is the strongest acid?

a. CH4
b. HCCH
c. CH2=CH2
d. CH3CH3
24. Which of the following is the definition of a pair of diastereomers?
a. A pair of stereoisomers that are not mirror images of one another
b. A pair of structures that are superposable mirror images of one another
c. A pair of stereoisomers that are non-superposable mirror images of one another
d. A pair of stereoisomers that have equal specific rotations
25. What is the correct assignment of common names for the following molecules?

a.
b.
c.
d.

i = butane; ii = isobutane; iii = isopentane

i = butane; ii = neopentane; iii = isopentane
i = butane; ii = isobutane; iii = neopentane
i = neobutane; ii = isobutane; iii = pentane

ID: A

CH310/318M-Exam I
Answer Section v2.0
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:

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

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 #1
PART 2:

Free Style Answer Format

KEY

(75 pts in this section)

1) Draw the staggered conformations (Newman projections) of 1-chloropropane. Label each

as gauche, anti etc. and circle the most stable conformer. (16 pts)

2) Draw all the stereoisomers of 1,3-dichlorocyclopentane. Label cis, trans and meso, (if there
are any meso isomers, show the plane of symmetry). Label any enantiomers. You may use
flat drawings for this question. (13 pts)

plane of symmetry

Cl
H

Cl

Cl

Cl

Cl

Cl

cis-1,3dichlorocyclopentane
(achiral, meso compound)

trans-1,3-dichlorocyclopentane
pair of enantiomers

UTEID

CH 310/318 M EXAM #1

KEY

3) Conformers Convert each of the compounds below to the most stable Newman projection
around the indicated bond. (12 pts)

4) Configurational isomers. Draw and label the enantiomers of 2-butanol. You must show the
stereochemistry of the chiral centers and label as R or S. (10 pts)

UTEID

CH 310/318 M EXAM #1

KEY

5) Conformations in cyclic systems: Using chair drawings, show two conformations of cis
1-chloro-3-methylcyclohexane. (14 pts)
A) Indicate the positions of the chloro and methyl substitutents and clearly label them as
axial or equatorial.
B) Indicate which of the chair conformations is the most stable and why.

es
ur
t
uc
e tr
ar e s
e
es sam
Th he
t

UTEID

CH 310/318 M EXAM #1

KEY

6) Resonance structures: Using curved arrows, show the various resonance contributors for
each of the following structures and intermediates. (Note: more than 2 drawings are possible
for some examples.) (10 pts)

END OF EXAM