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:
KEY
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
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
Ph3P
Ph
OR
Ph3P
Ph
Ph
HOCH2CH2OH
H3O+
Br
H
Br
H
OH
1) Mg
2) CH3CH2CH2CHO
O
H
PCC
CH2Cl2
HCl ( aq)
H
O
H
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+
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
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
CH2I2
(CH3)2CuLi
Cu(Zn)
Br
CH3
12
CH3