Chapter 5 - Aromatic Compounds

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

a. 2,4-dibromotoluene
b. 2,4-dibromophenol
c. 2,4-dibromoaniline
d. 4,6-dibromophenol

ANS: B

2. What is the IUPAC name of the following compound?

a. 3-bromo-4-nitrobenzaldehyde
b. 2-bromo-1-nitro-4-benzoic acid
c. 3-bromo-4-nitroacetophenone
d. 3-bromo-4-nitrobenzoic acid

ANS: D

3. Which of the following compounds is aromatic?

a. ethane
b. cyclobuta-1,3-diene
c. benzene
d. cycloocta-1,3,5,7-tetraene
ANS: C
 4. What is the major organic product obtained from the following reaction?

a. c.

b. d.

ANS: C

5. Which of the following undergoes the most rapid bromination upon treatment with Br2/FeBr3?
a. benzene
b. nitrobenzene
c. bromobenzene
d. benzaldehyde

ANS: A

6. Which of the following undergoes the most rapid acylation upon treatment with acetyl chloride and
AlCl3?
a. benzene
 b. toluene
c. chlorobenzene
d. 1,4-dichlorobenzene

ANS: B

7. Which of the following sets of substituents are all o/p-directing in electrophilic aromatic substitution
reactions?
a. Cl, CH3, CN
b. Br, OH, COCH3
c. Cl, OH, CH3
d. CN, NO2, COCH3

ANS: C

8. Which of the following sets of substituents are all deactivating groups in electrophilic aromatic
substitution reactions?
a. Cl, CN, NO2
b. Cl, NH2, CH3
c. CH3, OCH3, COCH3
d. CH3, NH2, OCH3

ANS: A

9. What is the major organic product obtained from the following reaction?

a. c.
 b. d.

ANS: A
10. An accurate description of the structure of benzene is:
a. The bonds are quickly moving around the ring.
b. There are two distinct structures that are in equilibrium.
c. All the carboncarbon bonds are equal in length.
d. There are distinct single and double bonds.
e. Some bonds are longer than others.

ANS: C

11. Which of the following is a correct statement regarding electrophilic aromatic substitution?
a. The carbocation intermediate will lose a proton to regain aromaticity, usually from a
position other than the site of electrophilic attack.
b. Formation of the carbocation intermediate has a high activation barrier due to loss of
aromaticity.
c. The carbocation intermediate has several resonance structures and is negatively charged.
d. Re-formation of the aromatic ring has a low activation barrier and therefore occurs slowly.
e. Many suitable electrophiles are unreactive and can be stored for long periods of time prior
to use.

ANS: B

12. Place the following in order of reactivity towards electrophilic aromatic substitution.
a. I > II > III > IV
b. I > II > IV > III
c. II > I > III > IV
d. II > I > IV > III
e. III > IV > II > I

ANS: B
 13. What is the correct assignment of the names of the following aromatic compounds?

a. 1 = anisole; 2 = furan; 3 = pyrimidine

b. 1 = aniline; 2 = pyrrole; 3 = pyridine
c. 1 = anisole; 2 = pyridine; 3 = pyrrole
d. 1 = aniline; 2 = imidazole; 3 = pyridine

ANS: B

14. Draw the structure of 4-bromo-2-fluorotoluene.

ANS:

15. Draw the resonance structures for acenaphthene.

ANS:

16. Circle the compound(s) in the following set that will undergo both substitution and addition when
treated with Br2.
 ANS:

17. Consider the production of 1-bromo-4-nitrobenzene:

a) Explain why Pathway A for the production of 1-bromo-4-nitrobenzene produces a higher

yield of the product.

b) If reaction Pathway A is carried out at high temperatures, a trisubstituted product forms.

Draw the structure of the product and explain why it forms.

ANS:
a) Bromine is an o/p-director while the nitro group is a meta director.

b)

Bromine is an o/p-director while the nitro group is a meta director. Both groups direct the
second NO2 to the same position--the position that is ortho to Br and is also meta to NO2.
 18. Consider the following sequence of reactions:

a) What is the major

organic product
obtained from the
sequence of
reactions?

a. b. c. d.

b) If KMnO4 had been

replaced by
Na2Cr2O7, what
would be the final
product of the
reaction?

ANS:
a) c

b) No change, the product would still be the oxidation of the alkyl side chain.

19. Draw the major product of the following reaction:

ANS:
 20. Consider the following compound:

a) Provide the correct IUPAC name for the compound.

b) Draw and name the other isomeric nitrotoluenes.

ANS:
a) m-nitrotoluene or
1-methyl-3-nitrobenze
ne

b) p-nitrotoluene o-nitrotoluene
1,4-nitrotoluene 1,2-nitrotoluene

Instructions: Consider the reaction below to answer the following question(s).

21. Refer to instructions. The nucleophile in the reaction is indicated by letter _____.

ANS: A

22. Refer to instructions. The Lewis acid catalyst in the reaction is indicated by letter _____.

ANS: C
23. Refer to instructions. This reaction proceeds _____________ (faster or slower) than benzene.

ANS: slower
 24. Refer to instructions. Draw the structure of product D.

ANS:

25. Which of the following heterocycles is aromatic?

a.

b.

c.

d.

ANS: A, B, D

26. Circle the aromatic portion of the following molecule:

 ANS:

27. Circle the aromatic portion of the following molecule:

ANS:

28. Draw the structure of m-fluoronitrobenzene.

ANS:

29. Draw the structure of p-bromoaniline.

ANS:
 30. Draw the structure of o-hydroxybenzoic acid.

ANS:

31. Draw the structure of 3,5-dimethylphenol.

ANS:

32. Draw the structure of p-chlorobenzaldehyde.

ANS:

Instructions: Provide the IUPAC name for each of the following compounds.

33. IUPAC Name:

ANS: m-nitrotoluene

34. IUPAC Name:

ANS: isopropylbenzene or cumene
 35. IUPAC Name:

ANS: cis-1-methyl-3-phenylcyclohexane

36. IUPAC Name:

ANS: 2,4-diaminotoluene

37. IUPAC Name:

ANS:
(E)-2,3-diphenyl-2-butene

Instructions:
Consider the Friedel-Crafts alkylation reaction below to answer the following questions:

38. Draw the structure of the electrophile in this reaction.

ANS:

39. What is the role of the AlCl3 in the reaction?

 ANS:
The AlCl3 is a Lewis acid catalyst that assists in the ionization of the alkyl halide to give the
carbocation electrophile.

40. On the structures provided below, draw arrows showing the complete stepwise mechanism for this
reaction.

ANS:

Instructions:
Given the major organic product(s) of each of the following reactions. If no reaction is predicted,
write "N.R."

41. Write the product:

ANS:

42. Write the product:

ANS:
 43. Write the product:

ANS:

44. Write the product:

ANS:

45. Write the product:

ANS:
 46. Write the product:

ANS:

47. Write the product:

ANS:

48. Write the product:

ANS:
 Instructions:
Choose the best reagent(s) from the list provided below for carrying out the following conversions.
Place the letter of the reagent in the box beside the reaction number over the arrow. There is only one
answer for each reaction.

a. KMnO4, H3O+
b. Br2, FeBr3
c. Cl2, FeCl3
d. CH3Cl, AlCl3
e. HNO3, H2 SO4

49. Choose the best reagents:

ANS:

50. Choose the best reagents:

ANS:
 Instructions:
Starting with benzene or toluene, how would you synthesize these compounds? Assume ortho and
para isomers can be separated.

51. Synthesize:

ANS:

52. Synthesize

ANS: