Useful Information:
order
Rate Law
Integrated form
plot
slope
k (units)
half-life
0
rate = k
[A]t - [A]0 = -kt
[A] vs. t
-k
mol/L s
t1/ 2 
[ A] 0
2k
1
rate = k[A]
ln[A]t - ln[A]0 = -kt
ln[A] vs. t
-k
1/s
t1/ 2 
ln 2
k
2
rate = k[A]2
1/[A]t - 1/[A]0 = kt
1/[A] vs. t
k
L/mol s
t1/ 2 
1
k[A] 0
Arrhenius equation:
k = pze  Ea / RT
R = 8.314 J/K mol
k = Ae  Ea / RT
K = °C + 273
ln k = ln A - Ea/RT
ln (k2/k1) = (Ea/R)(1/T1 - 1/T2)
The following experimental data were obtained by measuring the initial rate of the
reaction shown below, under a variety of experimental conditions:
2 MnO4- + 5 C2H2O4 + 6 H+ → 2 Mn2+ + 10 CO2 + 8 H2O
[MnO4-] (M) [C2H2O4] (M)
Expt
1.0 x 10-3
2.0 x 10-3
2.0 x 10-3
1.0 x 10-3
1
2
3
4
1.0 x 10-3
1.0 x 10-3
2.0 x 10-3
2.0 x 10-3
[H+] (M)
Initial Rate (Ms-1)
2.0 x 10-4
8.0 x 10-4
1.6 x 10-3
4.0 x 10-4
1.0
1.0
1.0
2.0
1. (4) Which of the following is the correct rate law?
a)
b)
c)
d)
e)
rate = k [MnO4-]2 [C2H2O4] [H+]2
rate = k [MnO4-]2 [C2H2O4]2 [H+]
rate = k [MnO4-]2 [C2H2O4]
rate = k [MnO4-]4 [C2H2O4]2
rate = k [MnO4-]2 [C2H2O4]5 [H+]6
2. (3) The initial rate was measured as the change in concentration of MnO4with time. Determine the initial rate of the reaction in experiment 3, if it
were measured as the change in concentration of C2H2O4 with time.
a) 1.6 x 10-4 Ms-1
d) 4.0 x 10-3 Ms-1
b) 8.0 x 10-5 Ms-1
e) 1.6 x 10-2 Ms-1
c) 3.2 x 10-3 Ms-1
3. (4) At 25oC, the rate constant for this reaction is 2.00 x 105 M-2s-1. The
reaction has an activation energy, Ea, of 52.9 kJ/mol. What is the rate
constant at 35oC?
a) 1.00 x 105 M2-s-1 b) 3.00 x 105 M-2s-1 c) 4.00 x 105 M-2s-1
d) 6.00 x 105 M-1s-1 e) 8.00 x 105 M-1s-1
-1-
4. (4) The reaction:
A→B+C
is second order in A. When [A]o = 0.100 M, the reaction is 20.0% complete
in 40.0 minutes. What is the value of the rate constant, k, in M-1min-1?
a) 5.58 x 10-3
d) 12.0
b) 6.25 x 10-2
e) 16.0
c) 1.00
5. (3) Nitrogen dioxide (NO2) reacts with carbon monoxide (CO) in the following
reaction.
NO2 + CO  NO + CO2
Experimentally, the rate law was determined to be second order in NO2 and zero
order in CO. Which of the following mechanisms (a-d) explain the overall
stoichiometry and rate law for this reaction?
a) step 1
step 2
NO2 + NO2  N2O4
N2O4 + CO  NO + NO2 + CO2
(fast)
(slow)
b) step 1
step 2
NO2  NO + O
O + CO  CO2
(slow)
(fast)
c) step 1
step 2
NO2  NO + O
O + CO  CO2
(fast)
(slow)
d) step 1
step 2
NO2 + NO2  NO3 + NO
NO3 + CO  NO2 + CO2
(slow)
(fast)
e) None of the mechanisms (a-d) explain the rate law and stoichiometry
6. (3)
Which of the following statements about catalysis is always true?
a)
b)
c)
d)
e)
Ea forward reaction = Ea reverse reaction
Ea catalyzed reaction = Ea uncatalyzed reaction
H catalyzed reaction = H uncatalyzed reaction
Keq catalyzed reaction < Keq uncatalyzed reaction
Ea catalyzed reaction > Ea uncatalyzed reaction
-2-
An inorganic redox reaction proceeds via the following mechanism. Use this information
to answer the next three (3) questions.
step 1 (fast) Ag+ + Ce4+  Ag2+ + Ce3+
step 2 (slow) Tl+ + Ag2+  Tl2+ + Ag+
step 3 (fast) Tl2+ + Ce4+  Tl3+ + Ce3+
7. (3) What are the units of the overall rate constant, k?
a) s-1
b) Ms-1
c) M-1s-1
d) M2s-1
e) M-2s-1
8. (3) Which of the following reaction coordinates best describes the path of this
reaction?
a)
b)
P.E.
c)
P.E.
reaction coordinate
d)
P.E.
reaction coordinate
reaction coordinate
e) more information is needed
P.E.
reaction coordinate
9. (3)
Properly identify each of the following species:
a)
b)
c)
d)
e)
reactant
Ag+
Ce4+
Ag2+
Tl+
Tl2+
product
Tl3+
Tl3+
Tl2+
Ce3+
Ag2+
intermediate catalyst
Ce3+
Tl2+
2+
Tl
none
3+
Ce
Tl+
2+
Ag
Ag+
Ag+
none
-3-
Use the mechanism shown below to answer the next question.
10. (3) Which of the following statements is false?
step 2
step 1
product A
I
+ HBr
product B
II
a)
b)
c)
d)
e)
The major product is 3-bromo-2,3-dimethylpentane
I is the intermediate for the minor product
II is a tertiary carbocation
The nucleophile in step 1 is the  electrons
The H+ from the HBr acts as a catalyst in this reaction
Shown below is the structure of histidine, one of the essential amino acids.
Use this structure, and the labeled atoms in it, to answer the next three (3) questions.
1
N
NH2
2
3
N
H
4 C
HO
5
O
11. (3) What is the hybridization of each of the marked atoms?
a)
b)
c)
d)
e)
1
sp
sp2
sp2
sp3
sp2
2
sp2
sp3
sp2
sp2
sp2
3
sp3
sp3
sp3
sp2
sp3
4
sp3
sp3
sp3
sp2
sp3
5
sp2
sp2
sp2
sp
sp
12. (3) Which of the marked atoms corresponds to the energy diagram below?
a) 1
b) 2
c) 3
d) 4
E
13. (3) How many stereocenters are present in this molecule?
a) 0
b) 1
c) 2
d) 3
e) 4
-4-
e) 5
14. (4) How many different monobrominated products are made in the
reaction, in the presence of uv light?
2,3-dimethylpentane + Br2 → C7H15Br + HBr
a) 3
b) 4
c) 5
d) 6
e) 7
15. (3) Which of the following compounds shows the most stable conformation of
the major product of the reaction:
1,2-dibromocyclohexene + H2/Pt 
Br
Br
Br
Br
Br
c)
b)
a)
Br
Br
Br
Br
Br
e)
d)
16. (4) What is the correct IUPAC name for the compound shown below:
a)
b)
c)
d)
e)
3-sec-butyl-6-tert-butyl-2-methyloctane
7-tert-butyl-4-isopropyl-3-methylnonane
3,6,7-triethyl-2,2-dimethyloctane
3-ethyl-6-isopropyl-2,2,7-trimethylnonane
6-sec-butyl-3-tert-butyl-7-methyloctane
-5-
17. (3) Which of the pairs of compounds below shows the correct relative
boiling points?
higher boiling point
F
F
lower boiling point
Cl
Cl
C C
Cl
Cl
Cl
H
Cl
F
a)
b)
F
C C
Cl
C C
H
C C
Cl
H
CH3
CH3
c)
H
CH3 C CH3
CH3 CH CH2 CH3
CH3
CH3
d)
CH3 CH2 CH2 CH3
CH3 CH CH2 CH2 CH3
CH3
e)
18. (4) What is the correct IUPAC name for the molecule shown below?
a)
b)
c)
d)
e)
cis-3-propyl-4-octene
trans-3-propyl-5-nonene
cis-4-propyl-3-octene
trans-4-propyl-3-octene
trans-4-butyl-3-heptene
-6-
Use the following structures to answer the next two (2) questions:
3)
2)
1)
4)
5)
19. (3) Which of these compounds can exhibit geometric isomerism?
a) 1
b) 2
c) 3
d) 4
e) 5
20. (3) Which of these compounds are structural isomers of each other
(same formula)?
a) 1 and 2
b) 1 and 4
c) 2 and 3
d) 2 and 5
e) 4 and 5
21. (3) The acid catalyzed hydration reaction of a particular diene yields four
different products. The least abundant (minor) product is shown below:
OH
+
reactant + 2 H2O
H
HO
(minor product)
The reactant is:
a)
c)
b)
e)
d)
-7-
22. (3) Which of the following compounds shows the major product of the
following reaction, carried out in the dark:
1-methylcyclohexene + Br2 
a)
Br
b) Br
Br
c) Br
Br
Br
d)
Br
Br
e) none of the above
23. (3) What is the correct, IUPAC name for the reactant in the polymerization
reaction that produces the following product ( ignore geometric isomerism).
CH3
Br
CH3 Br
CH3
C
C
C
C
C
Br
CH2
Br
CH2
Br
CH3
a)
b)
c)
d)
e)
3,4-dibromo-3-pentene
1,2-dibromo-1-pentene
2,3-dibromo-2-pentene
1,2-dibromo-1-butene
2,3-dibromo-2-butene
-8-
CH3
n
24. (4) The following diol undergoes a two step process, a dehydration, followed by a
hydration. If only major products are formed, which of the following diols
represents the final product?
OH
+
+
H /H2O
H , dry
a)
OH
product
diene
OH
b)
OH
c)
OH
OH
OH
OH
d)
e)
OH
OH
OH
OH
In answering the following four (4) questions, consider the compounds I – VI and the
reagents a-d.
O
OH
OH
I
III
II
O
OH
O
OH
IV
V
VI
a) NaBH4
b) MnO4c) H2/Pt
d) LiAlH4
e) none of the reagents alone will allow this reaction to take place
25. (3) Treatment with which reagent will convert IV  III?
26. (3) Treatment with which reagent will convert II  III?
27. (3) Treatment with which reagent will convert I  VI?
28. (3) Treatment with which reagent will convert V  II?
-9-
29. (3) Given the following molecule, categorize it and describe what reactant
molecule(s) were used in its synthesis.
product
a)
b)
c)
d)
e)
O
OH
reactant
ketal
hemi-ketal
hemi-acetal
acetal
hemi-acetal
5-hydroxy-3,3,4-trimethyl-2-hexanone
5-hydroxy-3,3,4-trimethyl-2-pentanone
5-hydroxy-4,4-dimethylhexanal
5-hydroxy-3,3,4-trimethyl-pentanal
5-hydroxy-3,3,4-trimethylpentanal
30. (3) Which of the following chemical species (I - VII) are required to best carry out
the reaction leading the formation of the product shown below?
I. 2-methylbutanol
II. 2-methylpropanoic acid
III. 2-pentanol
IV. 2-methylbutanoic acid
V. 2-methylpropanol
VI H+/dry
VII H+/H2O
O
O
a) I, II and VI
d) IV, V and VII
b) II, III and VI
e) II, III and VII
c) IV, V and VI
31. (4) Which of the following reactions will not proceed as written?
O
a)
+
H
OH
OH
b)
+
O
O
+ H2 O
O
+
H , H 2O
O
O
c)
O
activator
+
+
2
OH
O
N
+ H2 O
N
OH
d) all of them will proceed as written
e) none of them (a-c) will proceed as written
-10-
Use the five structures shown below to answer the next three (3) questions.
OH
O
N
O
N
OH
O
I
O
IV
III
II
32. (3) Assuming that all five compounds have comparable molecular weights. Predict
order for the boiling points for these compounds, from highest to lowest, based
on the strength of the IMF.
a)
b)
c)
d)
e)
III > II > IV > V > I
IV > III > II > I > V
III > II > V > IV > I
IV > III > I > V > II
III > IV > V > II > I
33. (3) Which of these compounds are structural isomers of each other?
a) I and II b) I and III c) II and III d) IV and V e) none of them
34. (3) Which of these would you expect to be least soluble in water?
a) I
b) II c) III d) IV e) V
35. (3) What combination of reagents (I - VI) can convert the reactant completely to the
product in a two step process?
O
A
B
OH
O
I NaBH4
V LiAlH4
a)
b)
c)
d)
e)
A
IV
III
V
II
III
II H+ (dry) III H+/H2O
VI CH3OH/H+
B
VI
V
II
V
I
-11-
IV Cr2O72-
V
Answer Key
1. c
2. d
3. c
4. b
5. d
6. c
7. c
8. e
9. d
10. e
11. c
12. a
13. b
14. d
15. b
16. d
17. c
18. c
19. e
20. a
21.
22.
23.
24.
25.
26.
27.
28.
29.
30.
31.
32.
33.
34.
35.
a
d
c
a
e
c
b
e
c
b
e
b
b
e
b