LAST NAME: FIRST NAME:

UTEID:
COVER PAGE
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
CH 310/318 M
questions. Your answers to these questions must be Exam 3 v 2.0
submitted on a Scantron “bubble” sheet. The answer MWF 9-10
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
Question Value Score
exam. 1 18
Part II consists of questions for which you will need
to write out your answers, using structures and/or
2 22
words. This part of the exam will be hand-graded. 3 12
Answers for the Part II questions that are written in
pencil will not be eligible for re-grades. Answers
4 12
written in pencil with ink overlay will not be eligible 5 11
for re-grades. If you use a pen to answer the Part II
questions, only blue or black ink is acceptable.
Section II 75
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
Section I 75
will need to show it to the proctors when Raw Total 150
you turn in your exam.
2. Chapter 4 of the University’s “General
Information” catalog outlines this
Grade
university’s 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.
UTID: ________________________ November 2010

CH310/318M-Exam 3 VERSION 2

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(are) the major organic product(s) obtained from the following substitution reaction?

a. only 1
b. only 2
c. only 1 and 2
d. 1, 2 and 3

2. Which of the following reactions corresponds to a substitution?

a. tert-butanol → tert-butyl chloride
b. tert-butanol → 2-methylpropene
c. 3,3-dimethyl-2-butanol → 2,3-dimethyl-2-butene
d. cyclohexene → 1,2-dichlorocyclohexane

3. What is the equation for the rate of formation of 2-methoxypropane, (CH 3CH(OCH3)CH3, from the reaction of
2-bromopropane (i-PrBr) with sodium methoxide (NaOCH3)? (i-Pr = isopropyl)
a. Rate = k [NaOCH3]
b. Rate = k [i-PrBr]
c. Rate = k [i-PrBr]2
d. Rate = k [i-PrBr][NaOCH3]

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

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

1
5. What is the major organic product obtained from the following reaction?

a. 1
b. 2
c. 3
d. 4

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

a. 1-butene
b. trans-2-butene
c. cis-2-butene
d. butane

7. Which of the following solvents is the best choice for the reaction of 1-chlorohexane with sodium bromide?
a. toluene, PhCH3
b. water
c. hexane
d. dimethylsulfoxide

8. Which of the following anions is the most nucleophilic in polar protic solvents?
a. I−
b. F−
c. Cl−
d. Br−

9. What is the equation for the rate of formation of tert-butyl alcohol from the reaction of tert-butyl bromide (t-BuBr)
with water by an SN1 mechanism?
a. Rate = k [t-BuBr]
b. Rate = k [H2O]
c. Rate = k [t-BuBr][H2O]
d. Rate = k [t-BuBr]2

2
10. What is the geometry of the central carbon atom of a tert-butyl radical?
a. trigonal planar
b. square planar
c. tetrahedral
d. trigonal pyramidal

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

a. 2 moles of HBr
b. 2 moles of Br2
c. 1 mole of Br2
d. 1 mole of HBr

12. The reaction of 1-bromopropane with sodium iodide gives 1-iodopropane. What is the effect of doubling the
concentration of NaI on the rate of the reaction?
a. the rate remains the same
b. the rate increases by a factor of 4
c. the rate decreases by a factor of 2
d. the rate increases by a factor of 2

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

a. 2-methyl-2-butene
b. 2-methyl-3-heptyne
c. 2-bromo-3-methylbutane
d. 2-methyl-3-hexene

14. What type of reactive intermediate is formed in the reaction of propene with N-bromosuccinimide to give
3-bromo-1-propene?
a. allylic carbocation
b. allylic radical
c. cyclic bromonium ion
d. allylic carbanion

3
15. What is the major organic product obtained from the following reaction?

a. 3,3-dibromohexane
b. (E) 3,4-dibromohexene
c. 3,3,4,4-tetrabromohexane
d. 3,4-dibromohexane

16. Which of the following alkyl halides undergoes the fastest solvolysis reaction with methanol, CH3OH?
a. tert-butyl chloride
b. 2-chloropropane
c. ethyl chloride
d. methyl chloride

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

a. 1
b. 2
c. 3
d. 4

18. Which of the following is the best set of conditions for the preparation of tert-butyl methyl ether?
a. methanol and sodium tert-butoxide in tert-butanol
b. fluoromethane and sodium tert-butoxide in tert-butanol
c. tert-butyl fluoride and NaOCH3 in CH3OH
d. tert-butyl bromide and CH3OH

19. Which of the following is the most nucleophilic?

a. water
b. acetic acid
c. sodium ethoxide
d. methanol

4
20. What is the major organic product obtained from the following reaction?

a. 1
b. 2
c. 3
d. 4

21. What is(are) the major organic product(s) obtained from the following substitution reaction? (Hint: bromine atom
is equatorial in the reactant.)

a. only 1
b. only 2
c. only 3
d. a mixture of 1 and 2

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

a. 1
b. 2
c. 3
d. 4

5
23. What is the best choice of reagent(s) to perform the following transformation?

a. Na/NH3
b. BH3; followed by H2O2, NaOH
c. H2/Lindlar catalyst
d. (sia)2BH; followed by H2O2, NaOH

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

a. 1
b. 2
c. 3
d. 4

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

a. 1
b. 2
c. 3
d. 4

6
 ID: A

CH310/318M-Exam 3 VERSION 2
Answer Section

MULTIPLE CHOICE

1. ANS: D PTS: 3
2. ANS: A PTS: 3
3. ANS: D PTS: 3
4. ANS: A PTS: 3
5. ANS: A PTS: 3
6. ANS: C PTS: 3
7. ANS: D PTS: 3
8. ANS: A PTS: 3
9. ANS: A PTS: 3
10. ANS: A PTS: 3
11. ANS: C PTS: 3
12. ANS: D PTS: 3
13. ANS: B PTS: 3
14. ANS: B PTS: 3
15. ANS: A PTS: 3
16. ANS: A PTS: 3
17. ANS: C PTS: 3
18. ANS: D PTS: 3
19. ANS: C PTS: 3
20. ANS: C PTS: 3
21. ANS: A PTS: 3
22. ANS: A PTS: 3
23. ANS: D PTS: 3
24. ANS: B PTS: 3
25. ANS: B PTS: 3

1
CH 310/318 M EXAM #3 v 2.0 UTEID
KEY
PART 2: Free Style Answer Format (75 pts in this section)

1) Provide the the products 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. (18 pts)

7
CH 310/318 M EXAM #3 v 2.0 UTEID
KEY
2) When the solvent is used as the nucleophile in substitutions, the reaction is called a
solvolysis. The chiral bromobutene undergoes reaction with warm water to form three
products. Follow the instructions for the mechanism and account for the formation of all three
products-including any regio and stereochemistry. Hint: consider any rearrangements
and/or resonance structures. (22 pts)

Show the formation of the intermediates

H 2O

40oC
Br
H 2O H2O

Show the intermediates reacting with water

OH HO
OH
H H
H

H2O H2O H2O

Show the proton transfer and formation of the final products

OH OH OH

8
CH 310/318 M EXAM #3 v 2.0 UTEID
KEY
3) Mechanism The chlorination of n-propylbenzene gives 3 monochlorinated products and
each of these isomers with their relative amounts are shown below. In the boxes, show the
reactive intermediate which leads to the formation of each product and label which
intermediates is most stable, which is in the middle, and which one is least stable.
(12 pts)

Cl2

heat

Cl
Cl

65% Cl 10%
25%

9
CH 310/318 M EXAM #3 v 2.0 UTEID
KEY
4) Reactions. Provide the products for the following reactions. For full credit, show stereo and
regiochemistry where necessary. (12 pts)

Cl

CH3 Na CH3
OtBu

HO-tBu

Cl H

Na CN
H3C H3C CN
H
acetone

H H

10
CH 310/318 M EXAM #3 v 2.0 UTEID
KEY
5) Regioselectivity in free radical Reactions. The free radical bromination of 2-
methylpentane will give one major product. (11 pts)
a. Draw the major product in the box:

b. What is the initiation step in this reaction?

c. Draw the chain reaction steps:

H Br

HBr

Br Br
Br Br

END OF EXAM

11