LAST NAME:

FIRST NAME:

UTEID:
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 320 N
Exam I

Question
1
2
3
4
5
6
7
Section II

Value
18
8
12
14
12
14
12
90

Section I
Raw Total

60
150

Grade

Score

ID: A

320N_XM1
Answer Section
MULTIPLE CHOICE
1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
12.
13.
14.
15.

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

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

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

4
4
4
4
4
4
4
4
4
4
4
4
4
4
4

UTEID

CH 320 N EXAM #1
PART 2:

Free Style Answer Format

KEY

(90 pts in this section)

1) Reactions: Provide the products required for the following transformations.. (18 pt)

NHCH3
Ph

Ph

CH3

1) CH3NH2
2) H2; Ni

CH3

Ph

CH3

N2H4
O

KOH
Heat

Zn-Hg
HCl

Ph

CH3
1) EtMgBr
2) H3O+

NaBH4
MeOH
1) LiAlH4
2) H3O+

OH
Ph

OH
Et
Ph

CH3

OH
Ph

CH3

3 pts each box

CH3

UTEID

CH 320 N EXAM #1

KEY

2) Wittig Reactions: Provide a suitable Wittig (or stabilized Wittig) reagent for the following
transformations. (8 pts)
O
O

CH3

H3C

(EtO)2P

CO2Et

EtO2C

CH3

CH3
H3C

CH3

M UST be the E isomer

O

Ph3P

Ph

OR

Ph3P

Ph
Ph

4 pts per reagent

3) Multi-step synthesis: Provide the products for the following scheme. For full credit, you
must show the correct regiochemistry. (12 pts)

HOCH2CH2OH
H3O+

Br
H

Br
H

OH

1) Mg

2) CH3CH2CH2CHO

O
H

PCC
CH2Cl2

HCl ( aq)
H

O
H

3 pts per box

UTEID

CH 320 N EXAM #1

KEY

4) Texas two-step: Provide both the reagents (in square boxes) and the product (rounded
box) for these synthesis. In some of the steps, there is more than one correct method. (Note,
that a second reagent may be required in the square boxes. For example, the acid step of a
Grignard addition-please include it.) (14 pts-7 pts/scheme):

2 pts for reagent box must have all steps; 3 pts product box.
5) Multi-step synthesis: Provide the products for the following scheme. For full credit, you
must show the correct regiochemistry. (12 pts)

OH

Ph
Ph

1) PhMgBr

H2SO4
(conc)

2) H3O+

1) BH3
2) H2O2;
NaOH

Ph

Ph

Ph
Ph

H2SO4
(conc)

OH
Ph

1) PhMgBr
2) H3O+

2 pts each box.

10

Ph
O

H2CrO4

OH

UTEID

CH 320 N EXAM #1

KEY

6) Mechanism: Provide a mechanism for the following transformation. Show all important
flows of electrons, charges and intermediates. Where indicated, (in the structure-n-a- box)draw the intermediates. (14 pts)

H2O
H3CO

H
OCH3

loose a proton

OH2

H
O
CH3OH

add a proton
break-a-bond
H

H
H3CO

H3CO

OCH3

break-a-bond

H3CO

add a proton

CH3OH

OH2

H3CO

H2O

make-a-bond

OH

H
H3CO

OH

2 pts per step (7 steps)

11

loose a proton

OH2
OH

UTEID

CH 320 N EXAM #1

KEY

7) Synthesis: Provide the reagents for the following conversions. Note that some
transformations may require more than one chemical step. e.g. the acid step of a Grignard
reaction. For full credit, you must include and number these steps when necessary. (12 pts)

O
Ph3P

HBr

CH2
CH2

Br

KOtBu

CH2I2

HOtBu

Cu(Zn)

Br

Cannot be OHor MeO-

CH2I2

(CH3)2CuLi

Cu(Zn)
Br

CH3

2 pts per box

END OF EXAM SECTION

12

CH3