AMINES
1. Give an IUPAC name:
a)
b)
c)
d)
HO
NH 2
NH 2
CHO
NH
NH 2
NH 2
HO
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:
a) 4-isopropyl-1,3-benzenediamine
b) o-isopropylaniline
c) p-isopropylaniline
d) p-chloroaniline
e) m-aminoacetophenone
5. Describe procedures for preparing each of the following compounds, using acetic acid as
the source of all their carbon atoms.
a) ethylamine
b) N-ethylacetamide
c) diethylamine
d) N,N-diethylacetamide
6. Show by writing the appropriate sequence of equations how you could carry out each of the
following transformations.
a) 1-butanol to 1-pentylamine
b) tert-butyl chloride to 2,2-dimethyl-1-propylamine
c) isopropyl alcohol to 1-amino-2-methyl-2-propanol
d) 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
1
e) acetic anhydride
f) benzoyl chloride / NaOH
g) sodium nitrite / H2SO4, 0 oC
h) product g) heating in water
m) product g) + KI
n) product g) + HBF4
o) product g) + phenol
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:
a) p-nitrobenzonitrile
e) 1,3-dibromobenzene
b) 3,4,5-trichloroaniline
f) 1,2,3-tribromobenzene
c) 1,3-dibromo-5-nitrobenzene
g) 4-nitrobenzoic acid
d) 3,5-dibromoaniline
h) p-acetamidophenol (paracetamol)
10. Identify the principal organic product of each of the following reactions:
a)
O
H2 / Ni
NH 2
1. LiAlH4
b)
O
2. H2O
N
c)
OH
1. p-toluenesulfonyl chloride
pyridine
2.(CH3)2NH (excess)
O
d)
O
NH 2
O
e)
NaNO 2
NH
HCl, H 2O
f)
CH 3
CH 3
CH 3
N(CH 3)3
heat
OH
2