Exam

Name___________________________________

MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
1) Calculate the percentage of 1-chloro-2-methylbutane in the following reaction.

A) 23.14%

B) 13.88%

C) 27.77%

D) 35.18%

1)

E) 11.56%

2) Which of the following is a chain propagation step in the free radical chlorination of methane?
CH3 Cl
2 Cl
A) Cl + CH3
B) Cl2
CH3 + HCl
CH4 + CH3
C) CH4 + Cl
D) CH3 + CH4

2)

3) How many distinct dichlorination products can result when isobutane is subjected to free
radical chlorination?
A) 6
B) 4
C) 2
D) 1
E) 3

3)

CH2 Br2 + HBr was carried out. Which of the following

4) The reaction Br2 + CH3 Br
mechanism steps is productive, but relatively unlikely to occur?
Br2 + Br
HBr + CH2 Br
A) Br + Br2
B) Br + CH3 Br
CH3 Br
CH2 Br2
C) Br + CH3
D) Br + CH2 Br

4)

5) Calculate the percentage of 1-chloro-3,4-dimethylheptane formed in the following reaction.

5)

A) 16.96

B) 6.70

C) 26.80

D) 11.16

E) 22.32

6) Identify the most stable radical.

A)

6)

B)

C)
D)
E)

7) Calculate the percentage of 1-chloro-2-methylbutane in the following reaction.

A) 35.18%

B) 27.77%

C) 13.88%

D) 11.56%

7)

E) 23.14%

8) Which of the following represents the best preparation of 2-cyclopentenol from cyclopentane?
A) 1. Br2 , h 2. H2 O2
B) 1. NBS, CCl4 2. H2 O2 3. Br2 , CCl4 4. NaOCH3
C) 1. NBS, CCl4 2. Br2 , CCl4 3. NaOH
D) 1. Br2 , h 2. NaOCH3 3. NBS, CCl4 4. H2 O
E) 1. NBS, CCl4 2. NaOCH3 3. H2 O2

8)

9) If cyclohexane reacts with excess Cl2 at high temperature, how many distinct
dichlorocyclohexane products are possible? Include all stereoisomers.
A) 6
B) 8
C) 9
D) 5

9)
E) 7

10) Which of the following is the most stable radical?

A) I

B) II

10)

C) III

D) IV

E) V

CH2 Br2 + HBr was carried out. Which of the following

11) The reaction Br2 + CH3 Br
mechanism steps is both productive and relatively likely to occur?
CH2 Br2
CH3 Br
A) Br + CH2 Br
B) Br + CH3
HBr + CH2 Br
Br2 + Br
C) Br + CH3 Br
D) Br + Br2

11)

12) When (R)-2-bromobutane reacts with Cl2 /hv, which of the following is true?

12)

A)
B)
C)
D)
E)

II

Only I is formed.
Only II is formed.
I and II are formed in equal amounts.
I and II could never form under these conditions.
I and II are formed in unequal amounts.

13) Which of the following is not an intermediate or product in the reaction of

A) I

B) II

C) III

D) IV

13)

E) V

14) What is the major product of the following reaction?

A) I

B) II

C) III

14)

D) IV

E) V

15) Calculate the percentage of 3-chloro-3,4-dimethylheptane formed in the following reaction.

A) 22.32

B) 16.96

C) 11.16

D) 26.80

15)

E) 6.70

16) What reagent can best be used to convert cyclopentene to 3-bromocyclopentene in a single
step?
A) NBS,
B) Br2 , h
C) HBr
D) HBr with peroxide
E) none of the above

16)

17) Rank the free radicals (I-III) shown below in order of decreasing stability (ie, from most stable
to least stable).

17)

CH2 CH2 CH(CH3 ) 2

CH3 CH2 C(CH3 ) 2

II

CH3 CHCH(CH3 ) 2

III

A) II > I > III

B) III > II > I

C) II > III > I

D) I > III > II

E) I > II > III

18) When butane undergoes free radical bromination, the product mixture contains 98%
2-bromobutane and 2% 1-bromobutane. How many times more susceptible to hydrogen atom
abstraction is a secondary hydrogen in butane than is a primary hydrogen?
A) 100
B) 50
C) 73.5
D) 1.5
E) 8.7

18)

19) Which of the halogens below undergoes free radical halogenation with ethane most rapidly?
A) fluorine
B) bromine
C) chlorine
D) pyridine
E) iodine

19)

20) How many distinct monochlorinated products, including stereoisomers, can result when the
alkane below is heated in the presence of Cl2 ?

20)

A) 1

B) 2

C) 3

D) 4

E) 6

21) Which of the following is the rate-determining step for the monobromination of cyclohexane?

A) I

B) II

C) III

D) IV

E) V

22) Which of the following technique(s) can readily distinguish between:

A) NMR

B) IR

?
C) MS

D) A and B

21)

22)

E) A and C

23) Which of the following is antiaromatic?

A) I

B) II

23)

C) III

D) IV

E) V

24) Which of the following structures is the most important contributor to the resonance hybrid
formed when anisole undergoes o-bromination?

A) I

B) II

C) III

D) IV

E) V

24)

25) What is one of the products of the following reaction?

A) I

B) II

C) III

25)

D) IV

E) V

26) What is the major product of the following reaction?

A) I

B) II

C) III

26)

D) IV

E) V

27) Identify the best product for the reaction.

27)

A)

B)

C)

D)

E)

28) The name 2,4,6-tribromobenzene is incorrect. Which of the following is the correct name?
A) m,m-dibromobromobenzene
B) m,m,m-tribromobenzene
C) 3,5-dibromobromobenzene
D) tribromobenzene
E) 1,3,5-tribromobenzene

28)

29) What is the name of the following compound?

A)
B)
C)
D)
E)

29)

p -dichlorobenzene
1,4-dichlorobenzene
phenyldichloride
A and B
B and C

30) Identify the major product for the reaction.

30)

A)

B)

C)

D)

E)

31) What is the structure of p -toluidine?

A) I

B) II

31)

C) III

D) IV

32) Identify the major product(s) for the reaction.

E) V
32)

A)

10

B)

C)

D)

E)

33) What is the best method for the preparation of p -chlorotoluene in high yield?
A) start with p -aminotoluene; NaNO2 /HCl, 0C; CuCl
B) start with benzene; chlorinate; methylate
C) start with benzene; methylate; chlorinate
D) start with toluene; chlorinate
E) start with chlorobenzene; methylate

11

33)

34) Which of the following structures is the most important contributor to the resonance hybrid
formed when toluene undergoes para nitration?

A) I

B) II

C) III

D) IV

35) Give the best product(s) for the reaction.

34)

E) V
35)

A)

B)

12

C)

D)

E) no reaction
36) What is the structure of 3-phenylpentane?

A) I

B) II

36)

C) III

D) IV

E) V

37) Which of the following fails to produce benzoic acid when heated in the presence of acidic
sodium dichromate?
A) 2-phenylethanol
B) 1-phenylethanol
C) 2-phenylheptane
D) 1-phenylheptanol
E) 2-methyl-2-phenylheptane

13

37)

38) Which of the following substrates is an electron withdrawing group overall?

A) I

B) II

C) III

D) IV

39) Identify the best product for the following reaction.

A)

B)

C)

D)

E)

14

38)

E) V
39)

40) What is the major product of the following reaction?

A)
B)
C)
D)
E)

40)

I
II
III
A and B equally
A and C equally

41) Which of the following compounds reacts most rapidly with HNO3 /H2 SO4 ?
A) nitrobenzene
B) fluorobenzene
C) toluene
D) benzonitrile
E) anisole

41)

42) What is the proper name of the compound below?

42)

A)
B)
C)
D)
E)

m-butylhydroxybenzene
o -butylhydroxybenzene
ethyl phenyl ether
1-phenoxyethane
m-butylphenol

15

43) What is the structure of phenol?

A) I

B) II

43)

C) III

D) IV

44) Identify the best product for the following reaction.

A)

B)

C)

D)

E)

16

E) V
44)

45) Which of the following is the first step in the mechanism of bromination?

A) I

B) II

C) III

D) IV

45)

E) V

46) What is the structure of styrene?

A) I

B) II

46)

C) III

D) IV

17

E) V

47) Identify the best product for the following reaction.

47)

A)

B)

C)

D)

E)

48) Identify the best product for the following reaction.

18

LiBr

48)

A)

B)

C)

D)

E)

49) What is the major organic product of the reaction between benzene and isobutyl chloride in
the presence of AlCl3 ?
A) isobutylbenzene
B) chlorobenzene
C) n-butylbenzene
D) tert-butylbenzene
E) sec-butylbenzene

19

49)

50) Which of the following is most likely to be the first step in the general mechanism for
electrophilic substitution reactions?

A) I

B) II

C) III

D) IV

51) Identify the major product for the following reaction.

A)

B)

C)

D)

20

50)

E) V
51)

E)

52) Which of the following is not a correct statement concerning the Friedel-Crafts acylation of
benzene?
A) The acylium ion is often produced from an acyl chloride.
B) An alkyl group substitutes for a hydrogen.
C) The acylium ion is resonance stabilized.
D) More than one equivalent of Lewis acid must be used.
E) The benzene ring attacks an acylium ion.

52)

53) Name the following compound.

53)

A)
B)
C)
D)
E)

tert-hexylbenzene
2-phenylhexane
3-phenylhexane
sec-hexylbenzene
isohexylbenzene

21

54) Identify the best product for the following reaction.

54)

A)

B)

C)

D)

E)

55) Which of the following is one of the resonance contributors of the intermediate produced in a
Friedel-Crafts alkylation of benzene?

A) I

B) II

C) III

D) IV

22

E) V

55)

56) Predict the major organic product of the following reaction.

A) I

B) II

C) III

56)

D) IV

57) Identify the best product for the following reaction.

A)

B)

C)

D)

23

E) V
57)

E)

58) Which of the following is an aromatic hydrocarbon?

A) I

B) II

C) III

58)

D) IV

E) V

59) Which of the following is the electrophile that attacks the aromatic ring during nitration?
A) NO2 +
B) HNO3
C) NO2 D) NO2
E) HNO3 -

59)

60) Which of the following is aromatic?

60)

A) I

B) II

C) III

D) IV

24

E) V

61) What is the major product of the following Friedel-Crafts alkylation?

A) I

B) II

C) III

D) IV

61)

E) V

62) Which of the following is the electrophile that attacks the aromatic ring during sulfonation?
A) SO2 +
B) HSO4 C) HSO3 D) H2 SO4
E) HSO3 +

62)

63) Which of the following protons gives an NMR signal with the highest chemical shift value
(farthest downfield)?

63)

(CH3 ) 2 CH O CH2 CH2 CH3

1
2
3 4
5
A) 1
B) 2

C) 3

D) 4

E) 5

64) What is the ratio of the protons in the following compound?

A) 3:2

B) 6:2

C) 3:3:3:2

64)

D) 6:3:2

E) 9:2

65) Which of the following spectroscopic techniques uses the lowest energy of the electromagnetic
radiation spectrum?
A) NMR
B) X-ray
C) IR
D) visible
E) UV

25

65)

66) Predict the splitting pattern in the proton coupled 13C NMR spectrum for the following
compound.

A)
B)
C)
D)
E)

66)

A, G = quintet; B = quartet; D, E = triplet; C, F = doublet

A, B, G = quartet; C, D, E, F = doublet
A, B, G = triplet; C, D, E, F = singlet
A, G = triplet; B = doublet; D, E = singlet
A, G = quartet; B = triplet; D, E = doublet; C, F = singlet

67) How many signals would you expect to see in the 1 H NMR spectrum of the following
compound?

A) 3

B) 2

C) 4

D) 5

E) 1

68) What is the ratio of the protons in the following compound?

A) 3:2:1

B) 3:3:2

C) 3:1

68)

D) 6:2:1

69) Which of the following is used in nuclear magnetic resonance spectroscopy?

A) visible
B) infrared
C) X-ray
D) ultraviolet

26

67)

E) 3:2

E) radio

69)

70) How many signals would you expect to see in the 1 H NMR spectrum of the following
compound?

A) 2

B) 7

C) 3

D) 4

70)

E) 8

71) 1 H nuclei located near electronegative atoms tend to be ________ relative to 1 H nuclei which
are not.
A) split
B) deshielded
C) shielded
D) resonanced
E) none of the above

71)

72) Which of the following protons gives an NMR signal with the lowest chemical shift value
(farthest upfield)?

72)

F CH2 CH2 CH2 CH2 CH2 Br

1
2
3 4
5
A) 1
B) 2

C) 5

D) 4

E) 3

73) What splitting pattern is observed in the proton NMR spectrum for the indicated hydrogens?

A) septet

B) singlet

C) triplet

D) doublet

73)

E) quartet

74) If the frequency for flipping a 1 H nucleus at an applied field of 1.4092 Tesla is 60 MHz, what
would be the applied magnetic field if the frequency is 360 MHz?
A) 1.4092 Tesla
B) 8.4552 Tesla
C) 4.2577 Tesla
D) 3.0439 Tesla
E) 0.2349 Tesla

74)

75) How many signals would you expect to see in the 1 H NMR spectrum of the following
compound?

75)

A) 6

B) 5

C) 4

D) 3

27

E) 2

76) What splitting pattern is observed in the proton NMR spectrum for the indicated hydrogens?

76)

CH3 OCH2 CH2 OCH3

A) quartet

B) singlet

C) doublet

D) triplet

E) septet

77) Which compound has a 1 H NMR spectrum consisting of the following peaks: 0.9 (6H, d), 1.0
(3H, t), 2.2 (2H, q), and 4.0 (1H, septet)?
A) (CH3 ) 2 CHOCH2 CH3
B) (CH3 ) 2 CHCH2 CO2 CH3
C) (CH3 ) 2 CHCH2 O2 CCH3
D) (CH3 ) 2 CHCO2 CH2 CH3
E) (CH3 ) 2 CHO2 CCH2 CH3

77)

78) Give the integration and splitting pattern for each signal in the 1 H NMR spectrum.

78)

A)
B)
C)
D)
E)

a = 2H, triplet;
a = 3H, triplet;
a = 3H, triplet,
a = 2H, triplet;
a = 3H, triplet,

b = 3H, doublet; c = 2H, doublet; d = 1H, singlet

b = 2H, sextet; c = 2H, quartet; d = 1H, triplet
b = 2H, quintet; c = 2H, triplet; d = 1H, singlet
b = 3H, sextet; c = 2H, triplet; d = 2H, doublet
b = 2H, doublet; c = 2H, doublet,; d = 1H, singlet

79) What splitting pattern is observed in the proton NMR spectrum for the indicated hydrogens?

A) singlet

B) doublet

C) septet

D) triplet

80) Predict the integration for each proton in the 1 H NMR spectrum.

A)
B)
C)
D)
E)

a = 5H; b = 5H; c = 7H; d = 7H; e = 7H

a = 2H; b = 3H; c = 2H; d = 3H; e = 2H
a = 3H; b = 2H; c = 2H; d = 3H; e = 2H
a = 3H; b = 2H; c = 2H; d = 2H; e = 3H
a = 2H; b = 3H; c = 2H; d = 5H; e = 2H

28

79)

E) quartet
80)

81) Give the structure of a compound that has a formula of C8 H11N and has signals in the 13C

NMR spectrum at 25.9 ppm (CH3 ), 51.1 ppm (CH), 125.9 ppm (CH), 126.6 ppm (CH), 128.3
ppm (CH), and 148.5 ppm (C).
A)

B)

C)

D)

E)

29

81)