AMINES SOLUTIONS 97
1. Give the IUPAC name and where possible, the common name of the following:
a)
CH3
CH3CCH2
N
H
CH(CH3)2
(I) N-isopropyl-2,2-dimethyl-1-propanamine
(c) isopropylneopentylamine
CH3
b)
NH2
CH3CH2CHCH3
(I) 2-butanamine
(c) sec-butylamine
c)
CH3
N
(I) N-methyl-N-propylcyclohexanamine
(c) cyclohexylmethylpropylamine
CH2CH2CH3
d)
(I) 2-cyclopentylethanamine
CH2CH2NH2
e)
CH2NH2
(I) phenylmethanamine
(c) benzylamine
Page 1
AMINES SOLUTIONS 97
2.
Draw structures of the following compounds:
a) 3-aminobutanal
NH2
O
CH3CHCH2CH
b) 3-bromopyridine
Br
N
c) 2-aminopyrrole
H2N
N
H
d) N-methylpyrrolidine
N
CH3
e) tert-butylethylisopropylammonium hydroxide
CH3
CH3C
CH2CH3
N
+
CH(CH3)2
OH-
CH3 H
Page 2
AMINES SOLUTIONS 97
3. Give the approximate pKb of
a) an alkyl amine such as methylamine
3-4
b) an aromatic amine such as aniline
9 - 10
4. Write equations to show how the following amine can be synthesized from a suitable alkyl
halide. Show all reagents and catalysts and any intermediate products. Mechanisms are not
required. More than one step may be required.
CH2NH2
a) using sodium azide
b) using sodium cyanide
CH2Br
NaN3
Br
CH2N3
H2/Pt
CN
1 LiAlH4
2 H2O
NaCN
CH2NH2
CH2NH2
5. Draw the structures of the reagents needed to prepare the following amines by reductive
amination of an aldehyde and if possible a ketone. Show all possible sets of reagents.
O
NH2
+
HCCH2CH3
H2/Pt
NH
CH2CH2CH3
H2/Pt
O
+
NH2CH2CH2CH3
Page 3
AMINES SOLUTIONS 97
6. Write equations showing all the reagents needed and any intermediate products formed
producing t-butylamine by
a) Hoffman rearrangement
b) Curtius rearrangement
Hoffman Rearrangement
CH3 O
CH3C
C
CH3C
NH2
NaOH
CH3
CH3 O
CH3C
CH3
Br2
C
CH3
NH2
CH3
CH3C
Cl
CH3
CH3 O
NaN3
Curtius Rearrangement
H2O
C
N3
CH3C

NH2
CH3
CH3

-
H2O
N2
CH3
CH3
CH3C
H2O
N
CH3
C
O

isocyanate
CH3C
O
NH
C
OH
CH3 carbamic acid
7. Write equations showing the Hoffman elimination of the following compound. Show all
reagents and the major alkene product
CH3
CH3
CH
H
CH2
N
CH3
2 CH3I
CH3
CH2CH3
K2CO3
CH
CH3
I- CH3
CH2
+
N
CH3
Ag2O, H2O
CH2CH3
CH3
CH3CHCH2N
CH3
+
CH2
CH2
Page 4
AMINES SOLUTIONS 97
8. Write equations, including all reagents and catalysts, showing how p-bromoiodobenzene
should be prepared from benzene. The sequence must include the diazonium salt at some
stage. No mechanisms required.
O
O O
NO2
HNO3 , H2SO4
NH2
H2/Pt
NHCCH3
CH3COCCH3
Br2
O
NH2
HNO2 ,
H2SO4
+
N
1 H3O 
+
2 NaOH
or NaOH H2O 
Br
N HSO4-
NHCCH3
Br
I
KI
Br
Br
9. Write an equation showing the formation of ethanolamine from ethylene oxide. Show the
mechanism by pushing electrons.
.. : O:
O
NH3
..
+
CH2
CH2
CH2
+ NH
CH2
NH2CH2CH2OH
ethanolamine
3
10. Draw the structure of the carcinogenic nitrosamine formed when nitrous acid reacts with a 2°
amine.
2º amine
R
N
R
H
R
+
HO N O
H2O
+
N
N O
R
nitrosamine
(a yellow oily liquid)
Page 5
AMINES SOLUTIONS 97
11. Draw the structure of the product of benzenesulfonyl chloride plus
a) cyclopentylamine
b) dicyclopentylamine
H
+
SO2Cl
H2N
SO2 N
..
1° amine
SO2Cl
+
N-cyclopentylbenzenesulfonamide
SO2 N
..
HN
2° amine
N,N-dicyclopentylbenzenesulfonamide
12. Draw and label a micelle of an anionic surfactant
hydrophilic
ionic
head
Micelle
COOCOO-
-
OOC
hydrophobic
(lipophilic)
hydrocarbon
tail
OOC
100 - 200
soap
molecules
COO-
-
COO-
OOC
COO-
13. Write the formula and name of
a) a bar soap
b) a liquid soap
potassium laruate (liquid soap)
sodium laruate (bar soap)
COO
Na+
CO- K+
O
Page 6
AMINES SOLUTIONS 97
14. Write the formula of a cationic surfactant
+ CH3
CH3(CH2)n-N-CH3 ClCH3
n = 15-17
15. Explain why amides are non basic (pKb  17). Draw a structure and push electrons.
The lone pair of electrons on N is withdrawn to the carbonyl carbon by the
electronegative O
.. : O:
: O:
..
R
C
+
N
R
C
N
16. List the reagents required to convert an amide to:
a) a carboxylic acid
H3O+, 
NaOH, H2O, 
b) an carboxylic acid salt
17. In the following list, circle amines that are more basic than aniline and draw a box around the
ones that are less basic than aniline.
O
O
NO2
NH2
OCH3
NH2
NHCCH3
CNH2
NH2
O
NH2
NH2
CH
Br
CN
NH2
NH2
Electron withdrawing groups reduce the basicity of amines. Electron donating groups
increase the basicity of amines
Page 7
AMINES SOLUTIONS 97
18. Explain why aniline cannot undergo Friedel Crafts reactions
The amino group is a Lewis base. It reacts (donates its lone pair of electrons) to AlCl3,
which is a strong Lewis acid. The resulting complex is not nucleophilic.
..
-
+
NH2 AlCl3
NH2
+
AlCl3
19. Write equations for and show the mechanism of formation of p-aminoazobenzene from
aniline and benzenediazonium sulfate
+
+
N
..
HSO4N:
+
NH2
..
NH2
N
N
..
H
HSO4-
..
N
..
N
..
+
H2SO4
NH2
20. Explain what an emulsion is and give an example of one.
An emulsion is a stable mixture of 2 or more immiscible liquids held in suspension by a
small percentage of emulsifier.
e.g., o/w = oil in water emulsion such as milk. Water is the continuous phase and butterfat
is the disperse phase
e.g., w/o = water in oil emulsion such as butter. Water is the disperse phase and butterfat
is the continuous phase.
Page 8
AMINES SOLUTIONS 97
21. List 7 applications of cationic surfactants
a) they inhibit bacterial growth
b) they function as antistatic agents
c) they separate ores in floatation processes
d) they are corrosion inhibitors
e) used in hair conditioners
f) used in fabric softeners
g) their polymers are flocculants used to speed sedimentation
22. Write chemical equations showing the conversion of a fatty acid to a quat.
O
O
SOCl2
R
C
OH
O
NH3
R
C
Cl
R
C
NH2
NaOH
1 LiAlH4
2 H2O
R
CH2
+
N(CH3)3 Cl-
3 CH3Cl
R
CH2
NH2
NaOH
Page 9