Exam

Name___________________________________

MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the
question.

1) What is the IUPAC name of the following compound? 1)

A) para-ethylphenyl iodide
B) ortho-ethyliodobenzene
C) para-ethyliodobenzene
D) 1-ethyl-4-iodo-1,3,5-cyclohexatriene

2) How many isomeric dichlorobenzenes are there? 2)

A) 3
B) 4
C) no isomers - only a single compound
D) 2

3) How many isomeric tribromobenzenes are possible? 3)

A) four B) one C) two D) three

4) Which of the following would be a correct number of π electrons for a planar, 4)

monocyclic, completely conjugated polyene to be aromatic?
A) 8 B) 24 C) 3 D) 18

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5) What is the IUPAC name of the following compound? 5)

A) 2-tert-butyl-meta-chlorophenol B) 4-tert-butyl-5-chlorophenol
C) 4-tert-butyl-3-chlorophenol D) ortho-tert-butylchlorophenol

6) What is the IUPAC name of the following compound? 6)

A) 2-heptylbenzene B) 6-phenylheptane
C) 2-benzylheptane D) 2-phenylheptane

7) Which of the following groups are ortho/para directors? 7)

I. -NO2 II. -OCH3 III. -CO2CH3 IV. -CH3

A) I and III B) II and IV C) III and IV D) II and III

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8) Which of the following is 2-chloro-4-ethylphenol? 8)

A) B B) A C) C D) D

9) What is the correct IUPAC name of the following compound? 9)

A) 1,4-dibromo-2-nitrobenzene B) 1,4-dibromo-3-nitrobenzene
C) 2-nitro-1,4-dibromobenzene D) 1-nitro-2,5-dibromobenzene

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10) What is the IUPAC name of the following compound? 10)

A) 2,4-dichlorobenzoic acid B) 3,5-dichlorobenzoic acid

C) meta-dichlorobenzoic acid D) 4,6-dichloro-2-benzoic acid

11) Which of the following ions are aromatic species? 11)

A) III and IV B) I and III C) II and IV D) II and III

12) Identify the aromatic compounds. 12)

A) III and IV B) I and II C) I, II, and IV D) all of them

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13) The benzyl carbocation is shown below. Besides the benzylic carbon, identify any other 13)
carbon atoms that carry a partial positive charge based on resonance theory.

A) meta carbon atoms B) ortho and para carbon atoms

C) meta and para carbon atoms D) ortho and meta carbon atoms

14) Which of the following are consistent with the requirements for aromaticity? 14)

I. A system with delocalized π electrons in a ring.

II. 4n π electrons in the ring.
III. All the ring atoms must be carbons.
IV. (4n + 2) p electrons in the ring.
A) I and II B) I and IV C) I, II, and III D) I, III, and IV

15) Which of the following is an aromatic hydrocarbon? 15)

A) B B) A C) D D) C

16) The major product(s) in the nitration of benzoic acid is(are) 16)
A) meta-nitrobenzoic acid.
B) mixture of ortho and para-nitrobenzoic acid.
C) nitrobenzene and para-nitrobenzoic acid.
D) nitrobenzene.

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17) What is the value of n from Huckel's rule for the following aromatic compound? 17)

A) n = 3 B) n = 4 C) n = 9 D) n = 8

18) The name of the following compound is 18)

A) meta-bromonitrobenzene. B) meta-bromophenol.
C) meta-bromoaniline. D) meta-bromoanisole.

19) Nitration of benzoic acid has a reaction rate which is ________ than the nitration rate 19)
of benzene and gives primarily the ________ product(s).
A) faster, meta B) slower, ortho, para
C) faster, ortho, para D) slower, meta

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20) What is the hybridization of the nitrogen atom in pyrrole? 20)

A) sp B) 2p C) sp3 D) sp2

21) Identify the site of protonation when one equivalent of HCl is added to the compound 21)
below.

A) N-1
B) N-2
C) both N-1 and N-2 (about 50% each)
D) neither N-1 or N-2, the compound is not basic

22) Which statement is true of the hydrogenation of benzene? 22)

A) The ΔHhydrogenation of benzene is greater than three times that of cyclohexene.
B) The ΔHhydrogenation of benzene is less than three times that of cyclohexene.
C) The ΔHhydrogenation of benzene is equal to three times that of cyclohexene.
D) Benzene cannot be hydrogenated under any conditions.

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23) Which of the following aromatic compounds reacts faster than benzene in electrophilic 23)
aromatic bromination?

A) A B) D C) B D) C

24) Which one of the following is the electrophile in the reaction shown below? 24)

A) NO2+ B) H2SO4 C) benzene D) NO3¯

25) What is the electrophile in the Friedel-Crafts alkylation reaction below? 25)

A) AlCl3 B) benzene C) Cl¯ D) (CH3)3C+

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26) Rank the following compounds in order of decreasing reactivity to aromatic electrophilic 26)
bromination.

I. benzene II. toluene III. benzoic acid IV. phenol

A) II > I > IV > III B) II > III > IV > I
C) IV > II > I > III D) IV > III > II > I

27) Predict the effect the substituent attached to the benzene ring below would have on 27)
electrophilic aromatic substitution reactions.

A) meta director, activator B) meta director, deactivator

C) ortho/para director, deactivator D) ortho/para director, activator

28) In the Friedel-Crafts alkylation of benzene, dialkylation is often a significant 28)

by-product. In the Friedel-Crafts acylation of benzene, diacylation is not a significant
by-product. Which of the following is the primary reason for this difference?
A) Alkyl groups activate the ring to further substitution, acyl groups deactivate it.
B) Unlike acyl cations, carbocations can undergo rearrangements.
C) Acyl cations are more difficult to make with Lewis acids.
D) Alkyl groups are less sterically hindered than acyl groups.

29) Which isomer of dichlorobenzene gives a single mononitration product? 29)

A) ortho B) para C) meta D) none of them

30) Arrange the following compounds in order of increasing reaction rate with 30)
HNO3/H2SO4.

I. C6H5CH=O II. C6H5OCH3 III. C6H5Br IV. C6H5CH3

A) III < I < IV < II B) I < IV < III < II
C) III < I < II < IV D) I < III < IV < II

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31) What is the major product of the following reaction? 31)

A) 4-nitrophenol B) 1-ethyl-4-nitrobenzene
C) 4-ethyl-3-nitrophneol D) 4-ethyl-2-nitrophenol

32) Salicylic acid reacts with two equivalents of ICl to give one of the products below. 32)
Which one is it? (Hint: Cl is more electronegative than I.)

A) C B) D C) A D) B

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33) Identify the preferred site(s) of electrophilic attack on the following compound. 33)

A) ortho/para positions on ring 2 B) meta position on ring 1

C) meta position on ring 2 D) ortho/para positions on ring 1

34) Which one of the following compounds undergoes electrophilic aromatic sulfonation at 34)
the fastest rate?

A) B B) C C) A D) D

35) What is the product of the following series of reactions? 35)

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 A) D B) A C) C D) B

36) Nitration of chlorobenzene has a reaction rate that is ________ than the nitration rate of 36)
benzene and gives primarily the ________ product(s).
A) faster, meta B) slower, ortho/para
C) slower, meta D) faster, ortho/para

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37) Where would the compound shown below undergo bromination with Br2/FeBr3? 37)

A) meta position on ring 1 B) meta position on ring 2

C) ortho/para position on ring 1 D) ortho/para position on ring 2

38) Which one of the following substituents is deactivating and ortho-para directing in 38)
electrophilic aromatic substitution reactions?
A) -CH=CH2 B) -CO2H C) -Cl D) -N(CH3)2

39) Starting with toluene, which of the following is the best synthesis of 39)
meta-bromobenzoic acid?

A) A B) C C) D D) B

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40) Predict which position of the naphthalene compound below is the most reactive with 40)
electrophiles in electrophilic aromatic substitution.

A) C B) D C) A D) B

41) Identify the major product(s) of the reaction sequence shown below. 41)

A) meta-chlorobenzaldehyde B) meta-chloroacetophenone
C) ortho and para-chloroacetophenone D) ortho and para-chlorobenzaldehyde

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42) Which of the following is not a valid resonance form of the intermediate species in the 42)
reaction shown below?

A) D B) C C) B D) A

43) Ranked in order of decreasing reactivity in electrophilic aromatic substitution reactions, 43)
the order would be (more reactive > less reactive)
A) toluene > chlorobenzene > acetophenone
B) chlorobenzene > acetophenone > toluene
C) toluene > acetophenone > chlorobenzene
D) chlorobenzene > toluene > acetophenone

44) Which statement is true in electrophilic aromatic substitution? 44)

A) no meta directors have non-bonding electrons on the atom directly attached to the
ring
B) no meta directors have a nitrogen atom directly attached to the ring
C) all ortho/para directors make the ring more reactive than benzene
D) all ortho/para directors have non-bonding electrons on the atom directly attached
to the ring

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45) What would be the most efficient way to make meta-nitrobromobenzene? 45)

A) nitrobenzene + Br2/FeBr3
B) bromobenzene + HNO3/H2SO4
C) either of these approaches would work
D) neither of these approaches would work

46) What major product do you expect? 46)

A) C B) B C) D D) A

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47) Of the choices given, where would an aromatic substitution occur on this molecule? 47)

A) B B) D C) A D) C

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Answer Key
Testname:

1) C
2) A
3) D
4) D
5) C
6) D
7) B
8) B
9) A
10) B
11) D
12) C
13) B
14) B
15) A
16) A
17) B
18) C
19) D
20) D
21) A
22) B
23) D
24) A
25) D
26) C
27) B
28) A
29) B
30) D
31) D
32) B
33) A
34) D
35) D
36) B
37) C
38) C
39) B
40) B
41) B
42) D
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Answer Key
Testname:

43) A
44) A
45) A
46) C
47) A

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