AMINES

1. Give an IUPAC name:

a) b) c) d)

2. Provide a structural formula

a) 2-methyl-2-butylamine d) tetraethylammonium bromide

b) dibenzylamine e) N-allylcyclohexylamine

c) 1-phenyl-2-propylamine (amphetamine)

3. Identify the stronger base in each of the following pairs

a) 2-fluoroethylamine or ethylamine

b) methylamine, dimethylamine, trimethylamine, ammonia

c) aniline, cycklohexylamine, ammonia

4. Outline syntheses of each of the following arylamines from benzene:

1. 4-isopropyl-1,3-benzenediamine

2. o-isopropylaniline

3. p-isopropylaniline

4. p-chloroaniline

5. m-aminoacetophenone

5. Describe procedures for preparing each of the following compounds, using acetic acid as the source of all their carbon atoms.

1. ethylamine

2. N-ethylacetamide

3. diethylamine

4. N,N-diethylacetamide

6. Show by writing the appropriate sequence of equations how you could carry out each of the following transformations.

1. 1-butanol to 1-pentylamine

2. tert-butyl chloride to 2,2-dimethyl-1-propylamine

3. isopropyl alcohol to 1-amino-2-methyl-2-propanol

4. cyclohexanol to N-methylcyclohexylamine

7. Write the structure of the product formed on reaction of aniline with:

a) HBr i) product g) + CuCl

b) excess CH₃I j) product g) + CuBr

c) ethanal k) product g) + CuCN

d) product c) + H₂ / Ni l) product g) + H₃PO₂

e) acetic anhydride m) product g) + KI

f) benzoyl chloride / NaOH n) product g) + HBF₄

g) sodium nitrite / H₂SO₄, 0 ^oC o) product g) + phenol

h) product g) heating in water p) product g) + N,N-dimethylaniline

8. Write the structure of the product formed on reaction of acetanilide with:

a) LiAlH₄ e) acetyl chloride / AlCl₃

b) HNO₃ / H₂SO₄ f) HCl / H₂O reflux

c) SO₃ / H₂SO₄ g) NaOH / H₂O reflux

d) Br₂ / CH₃COOH h) tert-butyl chloride / AlCl₃

9. Each of the following compounds has been prepared from p-nitroaniline. Outline a reasonable series of steps leading to each one:

1. p-nitrobenzonitrile e) 1,3-dibromobenzene

2. 3,4,5-trichloroaniline f) 1,2,3-tribromobenzene

3. 1,3-dibromo-5-nitrobenzene g) 4-nitrobenzoic acid

4. 3,5-dibromoaniline h) p-acetamidophenol (paracetamol)

10. Identify the principal organic product of each of the following reactions:

2

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