CHM207 (ORGANIC CHEMISTRY )

TUTORIAL 9
CHAPTER 9: AMINES
1)

Give the IUPAC or common names for the following amines and classify
them as primary, secondary or tertiary amines.

CH3CH2CHCH3
NH2

a) (CH3)3-C-NH2

f)

NH2

N CH2CH3
CH2CH3

b)

g)

NH2
C6H5
NO2 C6H5

NH

c)

h)

H
N CH2CH3

d) (CH3)2NCH2CH2CH3

i)

CHM207 (ORGANIC CHEMISTRY )

H
N CH3
Br

2)

3)

e) NH2(CH2)4NH2

j)

Write the structural formula of each of the following compounds.

a) diethylamine

g) 2-aminoethanol

b) N, N-diethylaniline

h) tetra-n-butylammonium iodide

c) benzylamine

i) N-ethylaniline

d) triphenylamine

j) 4,4-dimethylcyclohexanamine

e) p-nitroaniline

k) 3-methyl-1-butanamine

f) sec-butylamine

l) N-ethyl-N-methylaniline

Rank each set of compounds in order of increasing boiling points. Give

reasons for your answers.
a) (CH3CH2)3-N, (CH3CH2CH2)2NH, CH3CH2CH2-O-CH2CH2CH3
b) CH3CH2-OH, (CH3)2-NH, CH3-O-CH3
c) (CH3CH2)3N, (CH3CH2)2NH, CH3CH2NH2

4)

Rank each set of compounds in increasing basicity.

a) NH3, CH3NH2, Ph-NH2
b) aniline, p-methylaniline, p-nitroaniline

5)

Predict the products when n-propylamine reacts with the following

reagents:
a) HCl
2

CHM207 (ORGANIC CHEMISTRY )

b) benzoyl bromide
c) propanoyl chloride
d) acetic anhydride

6)

Describe the chemical test to distinguish each of this compounds:

a) ethylamine and dimethylamine
b) triethylamine and n-butylamine
c) n-propylamine and aniline

7)

Write a balance equation for the reaction of phenylamine with bromine

water.

8)

State whether the following amines are primary (1), secondary (2) or
tertiary (3) amines.
i) (C6H5)3N
ii) C2H5NHCH2CH3
iii) C2H5NH2

9)

Write equations for the reactions of the following pairs of reactants. Give
the names of the compounds formed.
i) C2H5NH2 and HNO2
ii) C2H5NH2andCH3COCI

10)

Show how to convert each of the following products using a suitable

reagents and condition.
i)
CH3CH2CH2OH
CH3CH2CH2NH2
O

CH3CH2C

CH3

ii)
CH3CH2CH2OH