ARENES

1. Write a structural formula:

a) allylbenzene e) 2,4,6-tribromoaniline

b) m-nitrotoluene f) m-xylene

c) p-bromophenol g) (Z)-1-phenyl-1-butene

d) o-ethylanisole h) m-chlorostyrene

2. Give an IUPAC names:

a) b) c) d) e)

3. Write structural formulas and give acceptable names for all the isomeric

a) nitrotoluenes c) tetrafluorobenzenes

b) dichlorobenzoic acids d) tribromophenols

4. Give the structure of the expected product from the reaction of isopropylbenzene (cumene) with:

1. 3 mol H₂ / Pt

2. b) Na/ NH₃, EtOH (Birch reduction)

3. Na₂Cr₂O₇, H₂SO₄, H₂O

4. NBS / CCl₄

5. Give the structure of the expected product from the reaction of ethylobenzene with:

a) Br₂, h b) Br₂ / AlBr₃

6. Each of the following may be represented at least one alternative resonance structure. Write

such a resonance

a) b) c) d)

7. Give reagents suitable for effecting each of the following reaction, and write the principal

products:

1. nitration of tert-butylbenzene

2. nitration of phenol

3. bromination of toluene

4. sulfonation of anisole

5. Friedel-Crafts acylation of benzene with benzoyl chloride

8. Write equations showing how you could prepare each of the following from benzene or

toluene:

1. sec-butylbenzene h)1-bromo-2,4-dinitrobenzene

2. 1-bromo-2-phenylpropane i) 3-bromo-5-nitrobenzoic acid

3. 4-tert-butyl-benzyl bromide j) 2-bromo-4-nitro-benzoic acid

4. 1-chloro-3-nitrobenzene k) diphenylmethane

5. p-isopropylbenzenesulfonic acid l) 1-phenyl-1-octene

6. 3-bromo-4-methylacetophenone m) 1-phenyl-1-ctyne

7. 2-bromo-4-ethyltoluene n) 1,4-di-tert-butyl-1,4-cyclohexadiene

9. Write equations showing how you could prepare each of the following from anisole and any necessary organic or inorganic reagents:

1. p-methoxybenzenesulfonic acid c) p-methoxystyrene

2. 2-bromo-4-nitroanisole d) 4-bromo-2-nitroanisole

10. Suggest reagents suitable for carrying out each of the following conversions. In most cases more than one synthetic operation may be necessary.

1. Ph-Et → Ph-CHBr-CH₃

2. Ph-CHBr-CH₃ → Ph-CHBr-CH₂Br

3. Styrene → phenylacetylene

4. Phenylacetylene → 1-phenylbutane

5. Ph-CH₂CH₂OH → 4-phenyl-1-butyne

11. Suggest a suitable series of reactions for carrying out each of the following synthetic

transformations:

a) b) c)

12. What combination of acyl chloride or acid anhydride and arene would you choose to

prepare each of the following compounds by a Friedel-Crafts acylation reaction?

a) b) c) d)

1

---