University of New England CHEM 1020 Chapter 4 -- Aromatic Compounds MULTIPLE CHOICE 1)The structure of chlorobenzene is correctly represented by: D)                   E)                     C)                                                Which of the following structures accurately represents phenol?             D) E)                                                                                       C)                                      The name of the following molecule is:         toluene ethylbenzene cumene styrene anisole                                    What dibromobenzene can form only one tribromobenzene? o-dibromobenzene m-dibromobenzene p-dibromobenzene cumene styrene                                    Using the following monosubstituted benzene, which position would be meta to X?             1 2 3 4 5                                    Which of the following molecules is o-nitrophenol? D)                   E)                                                                                 C)                                                What is the name of the following molecule? PhCH2CH2CH=CH2 styrene 4-phenyl-1-butene 1-phenyl-3-butene 3-benzyl-1-propene allylbenzene                                        Which name(s) of the following molecule is/are incorrect?   styrene vinylbenzene ethylbenzene phenylethene a and b                                    How many dinitrobenzoic acids are possible? 4 5 6 7 8                                    Which of the following names represents more than one compound? dichlorobenzene   2-bromophenol o-nitrobenzaldehyde 2,4,6-trinitrotoluene cumene                                    How many different trisubstituted products are possible from the nitration of o-xylene? 1 2 3 4 5                                    Which position would be para to X?             1 2 3 4 6                                    What is the correct name for the following molecule?             o-bromobenzyl biphenyl bromide 2-bromodiphenylpropane bromobenzylbenzene o-benzylbromobenzene                                    Which alkylbenzene, C9H12, when nitrated can yield only one mononitro product?   D)                     E)                     C)                                                                The correct name for                         is   2-chloro-4-bromotoluene

University of New England

CHEM 1020

Chapter 4 -- Aromatic Compounds

MULTIPLE CHOICE

1)The structure of chlorobenzene is correctly represented by:

1. 1. D)

1. 2. E)

C)

2. Which of the following structures accurately represents phenol?
   1. 
      D)
   2. E)

3. The name of the following molecule is:

1. 1. toluene
   2. ethylbenzene
   3. cumene
   4. styrene
   5. anisole

4. What dibromobenzene can form only one tribromobenzene?
   1. o-dibromobenzene
   2. m-dibromobenzene
   3. p-dibromobenzene
   4. cumene
   5. styrene

5. Using the following monosubstituted benzene, which position would be meta to X?

1. 1. 1
   2. 2
   3. 3
   4. 4
   5. 5

6. Which of the following molecules is o-nitrophenol?
   1. D)

1. 2. E)

C)

7. What is the name of the following molecule?

PhCH₂CH₂CH=CH₂

1. 1. styrene
   2. 4-phenyl-1-butene
   3. 1-phenyl-3-butene
   4. 3-benzyl-1-propene
   5. allylbenzene

8. 
   Which name(s) of the following molecule is/are incorrect?

1. 1. styrene
   2. vinylbenzene
   3. ethylbenzene
   4. phenylethene
   5. a and b

9. How many dinitrobenzoic acids are possible?
   1. 4
   2. 5
   3. 6
   4. 7
   5. 8

10. Which of the following names represents more than one compound?
    1. dichlorobenzene

1. 2. 2-bromophenol
   3. o-nitrobenzaldehyde
   4. 2,4,6-trinitrotoluene
   5. cumene

11. How many different trisubstituted products are possible from the nitration of o-xylene?
    1. 1
    2. 2
    3. 3
    4. 4
    5. 5

12. Which position would be para to X?

1. 1. 1
   2. 2
   3. 3
   4. 4
   5. 6

13. What is the correct name for the following molecule?

1. 1. o-bromobenzyl
   2. biphenyl bromide
   3. 2-bromodiphenylpropane
   4. bromobenzylbenzene
   5. o-benzylbromobenzene

14. Which alkylbenzene, C₉H₁₂, when nitrated can yield only one mononitro product?

1. 1. D)

1. 2. E)

C)

15. The correct name for                         is

1. 1. 2-chloro-4-bromotoluene.
   2. o-chloro-p-bromotoluene.
   3. 1-bromo-3-chloro-4-methylbenzene.
   4. 4-bromo-2-chlorotoluene.
   5. m-chlorobromotoluene.

16. The structural formula for p-chlorobenzoic acid is:
    1. D)

1. 2. E)

C)

17. Which of the following statements about benzene is FALSE?
    1. the molecule is planar and each carbon is at a corner of regular hexagon
    2. there are two resonance structures of equivalent energy
    3. the bond angles are all 120º and the bond lengths are all 1.39Å
    4. the typical mechanism by which reactions occur is by addition
    5. each carbon in the benzene ring is sp² hybridized

18. Which statement about benzene is true?
    1. All six hydrogens in benzene are chemically equivalent.
    2. Benzene decolorizes bromine solutions.
    3. The molecule is planar, and each carbon is at the corner of a regular hexagon.
    4. Both a and c are true.
    5. Both b and c are true.

19. Which of the following is NOT an electrophile in an electrophilic aromatic substitution reaction?
    1. NO₂⁺
    2. (CH₃)₃C+
    3. SO₃
    4. Cl^-
    5. all are

20. In the mechanism for the nitration of benzene, what is the function of H₂SO₄?
    1. to act solely as a solvent
    2. to donate a proton to HNO₃
    3. to accept a proton from HNO₃
    4. to generate heat for reaction to occur
    5. to protonate the benzene ring

21. The predominant intermediate in electrophilic nitration of toluene is:
    1. 
       D)
    2. E)

C)

22. The predominant intermediate in the nitration of benzenesulfonic acid is:
    1. 
       D)
    2. E)

C)

23. Which of the following groups is a meta director?
    1. –Cl
    2. –COOH
    3. –OCH₃
    4. –OH
    5. –NH₂

24. In electrophilic aromatic substitution reactions, which of the following molecules are considered to be less reactive than benzene?
    1. 
       D)
    2. E)

25. Which of the following groups are ortho, para-directing?
    1. —CO₂CH₃
    2. —CONH₂
    3. —SO₃H

D)

E) —SCH₃

26. Among the following groups, which ones are meta-directing?

1. –Cl

2. –NO₂
3. –SO₃H
4. –CH₃
5. –COCH₃

1. 1 and 4
2. 1, 2 and 3
3. 2, 3 and 5
4. 2 and 5
5. 1 and 2

27. Which of the following molecules is the most reactive toward electrophilic aromatic substitution?
    1. 
       D)
    2. E)

28. Which group is both ortho-para directing and ring-deactivating?
    1. –Cl
    2. –CH₃
    3. –NO₂
    4. –CHO
    5. –OCH₃

29. The relative rates of nitration of the following are:

A) 1 > 2 > 3 > 4

B) 4 > 2 > 1 > 3

C) 2 > 1 > 4 > 3

D) 3 > 4 > 2 > 1

E)   3 > 2 > 1 > 4

30. The only group among the following that is m-directing is:

B)

D)

31. 
    Among the following groups, which ones are o,p-directing?

1. 1. 1, 3, and 5
   2. 1 and 5
   3. 2 and 4
   4. 2, 3, and 4
   5. 1 and 3

32. Which electrophile is used to make acetophenone from benzene?

A)    

D)    

33. The name of the product of the following reaction is:

1. 1. benzenesulfonic acid
   2. aniline
   3. benzoic acid
   4. nitrobenzene
   5. anisole

34. If p-nitrophenol is treated with chlorine in the presence of AlCl₃, the only trisubstituted product observed is:
    1. 2-chloro-4-nitrophenol
    2. 3-chloro-4-nitrophenol
    3. 3-chloro-5-nitrophenol
    4. 4-chloro-2-nitrophenol
    5. 4-chloro-3-nitrophenol

35. What is the name of the major product from the following sequence of reactions?

1. 1. aniline
   2. anisole
   3. benzoic acid
   4. phenol
   5. toluene

36. The expected product from the following reaction is:

1. 1. 
      C)
   2. D)

37. What is the final product of the following reaction sequence?

1. 1. D)

1. 2. E)

C)

38. The predominant product from sequential nitration and bromination of benzenesulfonic acid is:
    1. 
       D)
    2. E)

C)

39. The predominant product from the sequential bromination and nitration of benzene is:
    1. 
       D)
    2. E)

40. What is the product of the following reaction?

1. 1. 
      D)
   2. E)

C)

41. What is the best sequence of reactions to synthesize m-nitrophenol?
    1. D)

1. 2. E)

C)

42. Which is the best reaction sequence to synthesize m-bromobenzenesulfonic acid from benzene?

1. 1. 1) Br₂, AlBr₃, 2) H₂SO₄, SO₃
   2. 1) H₂SO₄, SO₃ 2) Br₂, AlBr₃
   3. 1) ethene, HF, 2) Br₂, AlBr₃
   4. 1) CH₃Cl, AlCl₃, 2) Br₂, AlBr₃
   5. 1) Br₂, AlBr₃, 2) CH₃COCl, AlCl₃

43. Which is the best sequence of reagents to use in synthesizing 2-chloro-4-nitrotoluene from benzene:
    1. Cl₂, FeCl₃; then CH₃Cl, AlCl₃; then HNO₃, H₂SO₄
    2. CH₃Cl, AlCl₃; then Cl₂, FeCl₃; then HNO₃, H₂SO₄
    3. CH₃Cl, AlCl₃; then HNO₃, H₂SO₄; then Cl₂, FeCl₃
    4. SO₃, H₂SO₄; then HNO₃, H₂SO₄; then Cl₂, FeCl₃
    5. HNO₃, H₂SO₄; then Cl₂, FeCl₃; then CH₃Cl, AlCl₃

44. Which is the best reaction sequence to synthesize p-bromobenzenesulfonic acid from benzene?

1. 1. 1) Br₂, AlBr₃, 2) H₂SO₄, SO₃
   2. 1) H₂SO₄, SO₃, 2) Br₂, AlBr₃
   3. 1) CH₃Cl, AlCl₃, 2) Br₂, AlBr₃
   4. 1) Br₂, AlBr₃, 2) CH₃COCl, AlCl₃
   5. 1) HBr, ethane, 2) H₂SO₄, SO₃

45. A common polycyclic aromatic hydrocarbon is named naphthalene. What is the structure of naphthalene?
    1. D)

1. 2. E)

C)