Question 1 d.

IV
Benzyne is a very reactive intermediate. As a result, it is very
difficult to track chemical reactions. How was its existence Question 7
demonstrated? Nitrogen ylides are very versatile and can be used in a
number of chemical reactions. Which of the following is a
a. By trapping the intermediate in a cycloaddition reaction of nitrogen ylides?
reaction
b. By separating it from the mixture by GC/MS a. Cannizzaro reaction
c. By separating it from the mixture by column b. Sommelet reaction
chromatography c. Blanc reaction
d. None of the above d. Friedel-Crafts reaction

Question 2 Question 8
Benzyne is the mechanistic intermediate for which of the Nitrogen ylides are very versatile and can be used in a
following reactions? number of chemical reactions. Which of the following
reactions is NOT a reaction of nitrogen ylides?
a. Nucleophilic additions
b. Electrophilic additions a. Stevens reaction
c. Cycloadditions b. Sommelet reaction
d. All of the above c. Wittig reaction
d. Friedel-Crafts reaction
Question 3
Chain reactions involving free-radicals occur in which of the Question 9
following orders? The Wittig reagent was allowed to react with and carbonyl
compound with the formula C10H12O. The name of the
a. Initiation, propagation, termination product was 4-phenyl-4-octene. What is the name of the
b. Initiation, termination, propagation carbonyl compound used?
c. Propagation, termination, initiation
d. Termination, propagation, initiation

Question 4 a. 1-phenyl-1-butanone
Given that the energy of a CH3-H bond is 104 kcal/mol and b. Acetophenone
that of an HO-H bond is 119 kcal/mol, what is the bond c. 2-phenyl-3-butanone
dissociation energy of the following reaction? d. Benzaldehyde

Question 10
a. 15 kcal/mol What are common methods for preparing benzyne?
b. -15 kcal/mol
c. 223 kcal/mol a. Elimination from organolithium or
d. -223 kcal/mol organomagnesium precursors
b. loss of neutral leaving group
Question 5
c. photolytic and/or pyrolitic methods
Given that the energy of a CH3bond is 104 kcal/mol, CH 3-Cl
d. All of the above
bond is 85 kcal/mol, H-Cl bond is 103 kcal/mol and that of an
Cl2 bond is 58 kcal/mol, what is the bond dissociation energy
Question 11
of the following reaction?
What is the major product of the radical reaction of 2-
methylbutane with Cl2?
a. 25 kcal/mol
b. -25 kcal/mol a. 2-chloro-2-methylbutane
c. 189 kcal/mol b. 1-chloro-2-methylbutane
d. -166 kcal/mol c. 3-chloro-2-methylbutane
d. 4-chloro-2-methylbutane
Question 6
Identify the most stable free radical.

a. I
b. II
c. III
Question 12 Question 17
Which halogen is most reactive in radical halogenations of Which of the following molecules is a sulfur ylide?
alkanes?

a. F2 a. I
b. Cl2 b. II
c. Br2 c. III
d. I2 d. IV

Question 13 Question 18
Which of the following is NOT a method for generating free Which of the following six-carbon molecules will form a single
radicals? chlorinated compound when reacting with chlorine in
presence of light.
a. Thermal cracking
b. Photolysis bond heterolysis
c. Homolysis of peroxides and azo compounds
d. Electron transfer
a. I
Question 14 b. II
Which of the following is NOT a precursor of Benzyne? c. III
d. All of them

Question 19
Which of the following Wittig reagents would be useful for
a. I
converting acetophenone into 1,1-diphenylethene?
b. II
c. III
d. IV

Question 15
Which of the following molecules is a nitrogen ylide?
a. I
b. II
c. III
d. IV
a. I
Question 20
b. II
Which statement about free radicals is incorrect?
c. III
d. IV
a. Free radicals contain an unpaired electron.
Question 16 b. Radicals are believed to be involved in degenerative
Which of the following molecules is a phosphorus ylide? diseases and cancers.
c. They are formed by heterolytic cleavage of bonds.

d. Radicals can either be neutral or ionic.

Question 21
a. I 1-chloro-3-methylhexane undergoes SN2 reaction with
b. II sodium ethoxide. This reaction yields low amount of
c. III products. However, addition of small amounts of sodium
d. IV iodide increases the rate of the reaction. Why?
 a. The charge of the sodium ion stabilizes the charge of d. E2
the chloride ion.
b. The iodide ion renders the ethoxide ion more
reactive.
c. Small amounts of alkyl chlorides are converted into
the more reactive alkyl iodides.
d. With the presence of NaI, the mechanism changes to Question 25
SN1. Vinyl chloride, shown below, does not react with sodium
hydroxide in SN2 reactions. Why?
Question 22
Compound A undergoes a rearrangement reaction and forms
compounds B and C. Based on the potential energy diagram
below, what can be said about compounds B and C in terms
of kinetics and thermodynamics?
a. Hydroxide is a weak nucleophile.
b. The sp2 carbon-chlorine bond is stronger than the sp 3
carbon-chlorine bond.
c. The chlorine atom is sterically crowded.
d. Both B and C

Question 26
What is the configuration at the carbons labeled 1 and 2 in
the following compound?

a. B is the kinetic and thermodynamic product.

b. B is the kinetic product, and C is the thermodynamic

product.
c. C is the kinetic product, and B is the thermodynamic
a. 1R, 2S
product.
b. 1S, 2R
d. C is the kinetic and thermodynamic product.
c. 1R, 2R
d. 1S, 2S
Question 23
Provide the IUPAC name, including stereochemical
Question 27
designation, for the following molecule.
What is the major product of the following reaction?

a. (2R,3R)-2,3-dibromopentane
b. (2S,3S)-2,3-dibromopentane
c. (2R,3S)-2,3-dibromopentane
d. (2S,3R)-2,3-dibromopentane

Question 24
Select the mechanism by which the reactants below will
react.

a. I
b. II
c. III
d. IV
a. SN 1
b. SN 2
c. E1
 a. I
b. II
Question 28
c. III
What is the relationship between the two compounds below?
d. IV

Question 32
Which of the following carbocations is most stable?

a. Same compound
b. Structural isomers
c. Enantiomers
d. Diastereomers a. I
b. II
Question 29 c. III
What reaction will the following compound most likely d. IV
undergo?
Question 33
Which of the following compound h as the IUPAC name of
(2R, 3R)-2, 3-dihydroxybutane?

a. SN 1
b. SN 2
c. E1
d. E2

Question 30
Which is the correct structural formula for the compound
formed according to the mechanism below (lone electron
pairs were omitted)?

a. I
b. II
c. III
d. IV

Question 34
Which of the following compounds is chiral?
a. I
b. II
c. III
d. IV

Question 31
Which of the following alkyl halides give only one alkene as a. I
the product in the E2 reaction? b. II
c. III
d. IV

Question 35
Which of the following compounds will be the most reactive
substrate in SN1 reactions? Question 40
Which of the following statements best describes an E2
a. (C2H5)3CCl reaction?
b. (C2H5)2CHCl
c. C2H5CH2Cl a. It involves a two-step mechanism.
d. (C2H5)3CF b. It involves a very reactive intermediate.
c. The rate of the reaction depends on the
concentration of the base.
Question 36 d. The rate of the reaction increases in polar solvents.
Which of the following compounds will most readily react in
SN1 reactions?
Question 41
Name the following compound.

a. I
b. II
c. III a. Phenylmagnesium bromide
d. IV b. Ethylphenylmagnesium bromide
c. Benzylmagnesium bromide
Question 37 d. Benzylicmagnesium bromide
Which of the following molecules is prochiral?
Question 42
The Grignard reaction is an important reaction to provide
which of the following?

a. I a. Carbon-carbon bonds
b. II b. Carbon-magnesium bonds
c. III c. Carbon-halide bonds
d. IV d. Magnesium-halide bonds

Question 38 Question 43
Which of the following statements about chirality is What happens to the chiral center when (R)-3-methyl-3-
incorrect? phenyl-4-heptanone reacts with phenylmagnesium bromide?

a. A chiral center is an atom that is tetrahedrally a. Inversion of configuration occurs.

bonded to four different groups. b. A racemic mixture is formed.
b. A chiral molecule has a superimposable mirror c. Nothing, the chiral center remains unchanged.
image.
c. A chiral molecule does not have any reflective d. The product is achiral.
symmetry.
d. All chiral molecules may exist as enantiomers. Question 44
What is organometallic chemistry?

Question 39 a. The study of carbon containing compounds

Which of the following statements about the chemical b. The study of compounds containing a carbon-metal
reaction described below is true? bond
c. The study of metals
d. The study of salts

Question 45
What is the chemical structure of furan?
a. The product will have R configuration.
b. The product will have S configuration.
c. The product will be achiral.
d. The product will be a racemic mixture.
 a. I What is the name of the following heterocycle?
b. II
c. III
d. IV

a. Isoquinoline
b. Indole
c. Quinoline
d. Pyrrolidine

Question 46
Question 50
What is the IUPAC name for the imidazole molecule, shown
What is the name of the following heterocycle?
below?

a. Isoquinoline
a. Imidazole b. Indole
b. 1,3-imidazole c. Quinoline
c. Diazole d. Pyrrolidine
d. 1,3-diazole
Question 51
Question 47 What is the name of the following heterocycle?
What is the major product of the following reaction?

a. Thiazole
b. Indole
c. Quinoline
d. Pyrrolidine

Question 52
a. I Which of the following alkyl halides would be suitable to use
b. II when forming a Grignard reagent?
c. III
d. IV a. CH3CH2CH(OH)CH2Br
b. BrCH2CO2H
Question 48 c. PhCH2CH2Br
What is the major product of the following reaction? d. None of these are suitable

Question 53
Which of the following heterocycles is most basic?

a. I a. I
e. b. II b. II
f. c. III c. III
g. d. IV d. IV

Question 49 Question 54
Which of the following is an organometallic compound?

a. I
b. II
c. III
a. I
d. IV
b. II
c. III
d. IV

Question 55
Which of the following molecules is an heterocycle?
Question 59
Which of the heterocyclic compounds shown below is most
basic?

a. I
b. II
c. III
d. IV a. I
b. II
Question 56 c. III
Which of the following molecules will NOT be a product of d. IV
the following reaction?
Question 60
Which reagent is best for the reaction below?

a. I
b. II
c. III
d. All of the above
a. I
Question 57 b. II
Which of the following reactions would be a useful way of c. III
preparing 1-phenyl-1-butanol? d. None of the above

a. Butanal and phenylmagnesium bromide

b. 1-phenyl-3-butanone and NaBH4
c. Propanal and benzylmagnesium bromide
d. Both A and C

Question 58
Which of the heterocyclic compounds shown below is most
acidic?
ANSWER KEY 59. D
1. A 60. C
2. D
3. A
4. B
5. B
6. B
7. B
8. D
9. A
10. D
11. A
12. A
13. B
14. D
15. C
16. C
17. C
18. C
19. B
20. C
21. C
22. D
23. A
24. B
25. D
26. B
27. D
28. C
29. A
30. D
31. D
32. A
33. D
34. B
35. A
36. B
37. B
38. B
39. B
40. C
41. C
42. A
43. C
44. B
45. A
46. D
47. C
48. C
49. D
50. A
51. A
52. C
53. C
54. D
55. B
56. A
57. A
58. A