First Semester
Organic Chemistry
Five Sets of Practice Exams
2000 -2006
H
H
N
H
H
Cl
H H
Prof. J. W. Keller
i
Cover: Molecular orbital (MO) description of the transition state of the
nucleophilic substitution reaction between ammonia and chloromethane. In the
transition state the N-C bond is beginning to form, and at the same time the
C-Cl bond is breaking. This diagram shows the non-bonding MO of ammonia,
which is the electron pair donor, beginning to overlap with one end of the σ*
MO of the C-Cl bond, which is the electron pair acceptor.
This surface was generated using the Gaussian 03 ab initio program using the
WebMO server at the University of Alaska Fairbanks Department of Chemistry
and Biochemistry. www.uaf.edu/chem/WebMO. Similar results could be
obtained with HyperChem or other quantum chemistry programs.
ii
Table of Contents Five Semesters of Chem 321 Exams (2000-2006)
Including Chapters in McMurry’s Organic Chemistry, 5th and 6th Editions
Table of Contents .............................................................. i
Introduction ..................................................................... iii
Typical Exam Reference Sheet (constants and equations) ....... iv
Spectral Reference Tables .................................................. v
Page
Year
Chapters
Topic
2000
5th Ed
Quiz 1
Quiz 2
Quiz 4
Quiz 5
Quiz 6
Quiz 7
Quiz 8
Hour 1
Hour 2
Hour 3
Final
1,2
3,4
7
8
11
12, 13
15
1-6
7-10
11-15
1-16
Structure and bonding
Alkanes
Alkene Reactions
Alkynes
Nucleophilic Substitution
NMR, IR, and MS
Benzene
1
2
3
4
5
6
8
9
13
17
21
2002
5th Ed
Quiz 1
Quiz 2
Quiz 3
Quiz 4
Quiz 5
Quiz 6
Quiz 7
Quiz 8
Quiz 9
Hour 1
Hour 2
Hour 3
Final
1,2
3,4
5,6
7
8
9
11
12, 13
14
1-6
7-10
11-14
1-16
Structure and bonding
Alkanes
Alkenes
Alkene Reactions
Alkynes
Stereochemistry
Nucleophilic Substitution
NMR, IR, and MS
Conjugated Dienes
30
31
32
33
34
35
36
37
39
40
45
50
54
2003
6th Ed
(no quizzes given 2003-2006)
Cover Page
Hour 1
Hour 2
Hour 3
Hour 4
Final
61
62
65
69
73
77
1-4
5-8
9-12
13-16
1-16
i
2004
6th Ed
Hour
Hour
Hour
Hour
Final
1
2
3
4
1-4
5-8
9-12
13-16
1-16
82
85
89
93
98
2006
Hour
Hour
Hour
Hour
Final
1
2
3
4
1-4
5-8
9-12
13-16
1-16
104
108
112
117
121
ii
Introduction
This book is a complete set of quizzes and exams given in five semesters
of Chemistry 321, Organic Chemistry I, at the University of Alaska Fairbanks in
'00, '02, '03 and '04, and ‘06. Chem 321 is the first semester of a twosemester series dealing with the concepts, facts, and problem solving methods
of organic chemistry. This course is lecture only. Organic chemistry laboratory
is given as a separate course (Chem 324), which accompanies the 2nd
semester lecture course, Chem 322. Chemistry 321 covers the first half of
McMurry’s Organic Chemistry, either 5th or 6th Edition. The students taking the
course major mostly in chemistry, biochemistry, or biology (pre-med).
The exams in this book are typical of those given in “sophomore organic”
at smaller universities. At many larger universities the exams are made up of
multiple choice questions, whereas this course requires written responses from
the student. [One exception to this pattern is the University of Michigan
organic chemistry taught by Brian Coppola and colleagues.] The chapters and
chapter topics covered by each quiz and exam are included in the Table of
Contents. (The 5th & 6th Editions of McMurry are very similar in chapter
organization.)
Typical questions are of the following type:
-Given the name, write the structural formula
-Given the structural formula, write the IUPAC name
-Predict the major product, given starting material and rxn conditions.
-Suggest a several-step laboratory synthesis for a given compound
-Predict, and justify, the order of reactivity toward certain reaction
conditions
-Guess the structure given NMR and IR spectra
-Predict, and explain your prediction, which acid is stronger.
Studying with these exams
In a departure from previous editions, this book does not include
answers. You as an organic student should formulate your own answer key
after you have attempted the quiz or exam. The following quote is from Brian
Coppola of the University of Michigan regarding the use of their "coursepack"
of old exams.
Organic chemistry (and, just to editorialize a bit, any respectable
university course) asks you to learn AND apply the ideas... That is why
using the coursepack of old exams has to be approached thoughtfully:
those facts will not be on your tests... but the processes will be. Those
pages are the actual exam pages. The students who took those exams
did not have an answer key. Those exams are the chance to PRACTICE
the process without the safety net of an answer key.
If you wish to maximize your exam performance in this course, first
study the assigned problems and be able to do them independently of the
text; second, use this book; third, read Conquering Test Anxiety by Fiore and
Pescar, or Aceing College by Halberstram.
iii
Useful data, equations, constants, and conversion factors
K (temperature in Kelvins) = ºC + 273.15
ΔG o = ΔH o − T ΔS o
R (gas constant) = 8.314 J/K-mol = 1.987 cal/K-mol
K eq = e
h (Planck’s constant)= 6.62 x 10-34 J-sec
ε = hν =
c (speed of light in vacuum)= 3.00 x 108 m/sec
1 micrometer = 10-6 m
Y
-F
-Cl
-Br
-OH
-CH3
-CH2CH3
-CH(CH3)2
-C(CH3)3
-C6H5
− ΔG o
RT
[α ]D =
strain of one H-Y 1,3diaxial interaction
(kJ/mol)
0.6
1.0
1.0
2.1
3.8
4.0
4.6
11.4
6.3
hc
λ
α
l×c
pH = pK a
1.008
iv
[A ]
+ log
−
[AH ]
v
Chem 321
Quiz 1, Chap 1&2 McMurry 5th Ed
Name____________________________________
15 Sept 2000
1. For EACH of the molecules displayed on the screen: Draw a correct line-bond formula (Lewis) formula
showing single and double bonds, and non-bonding pairs. If different resonance forms are possible, just
show only ONE. (12 pts)
2. Considering BOTH molecules in question 1: (9 pts)
(A) How many sp3-hybridized carbons are there? Put the number inside this box:
(B) How many sp2 hybridized carbons are there? Put the number inside this box:
(C) How many sp hybridized carbons are there? Put the number inside this box:
-
3. Draw the resonance forms of an anion (C4H4NO2 ) with the following connection map:
(9 pts)
O
H
N
C
C
C
C
H
H
O
H
1
Chemistry 321
Name____________________________________________
Quiz 2, Chap 3,4 McMurry 5th Ed, Alkanes and Cycloalkanes
22 September 2000
PLEASE ALSO PUT YOUR NAME ON THE BACK AT THE TOP RIGHT.
SET.
YOU MAY USE A MODEL
1. Provide correct IUPAC names for each of the following compounds. (The arrow relates to Q2) (10 pts)
H3C
CH3
CH3
H
CH3
CH3
H3C
H
CH3
CH3
H3C
CH3
H3C
2. Using a Newman projection, illustrate ONE eclipsed
conformation of the C-C bond indicated by the arrow in Q1. (4 pts)
3. Referring to the following molecule, fill in the correct numbers in the boxes provides: (8 pts)
CH3
CH3
Number of equatorial hydrogens (on the ring C's) .................
Number of axial hydrogens (on the ring C's)..........................
Number of 1,3-diaxial hydrogen-methyl interactions..............
Number of gauche methyl-methyl interactions.......................
CH3
4. Draw the ring-flipped chair conformation of the molecule shown in Q3 above. Indicate which
conformation, the one shown in Q3 or the one in Q4, is more stable. Tell specifically why one is more stable
than the other. (8 pts)
2