TUTORIAL 1 ASC0303 ORGANIC CHEMISTRY

Alkanes and Cycloalkanes

1. Name the following compounds according to IUPAC
System:
a)

b
)
2-methylbutane

c)

3-ethylhexane

d
)
4-ethyl-3methyloctane

e)

4-(1-methylethyl)octane
or 4-isopropyloctane
f)

3-methyloctane

3methylpentane
1

g
)

h
)
(1methylethyl)cyclohexan
e
or
isopropylcyclohexan
e

(2,2dimethylpropyl)cyclohepta
ne
or neopentylcycloheptane
i)

j)

pentylcyclopantane

cyclopropylcyclopentane

2. Draw structures for the following compounds:

a. 2,2-dimethylpropane

or

b. 3-methylheptane

or

c. 4,5-diethylnonane

or

d. 4-(1-methylethyl)heptane

or

e. 5-(1,1-dimethylethyl)nonane or 5-tert-butylnonane
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f. 1-ethyl-4-methylcyclohexane

3. Draw all the possible isomers of the following.

a) C7H16

b) C6H14

c) C5H12
5

4.

4. Write Newman projections for all three staggered conformations of

2,2-dimethylpentane, looking down the C3-C4 bond.

5. Draw two different chair conformations of bromocyclohexane showing all hydrogen atoms.
Label all positions as axial or equatorial

6.

A.

Answer the following questions:

B.

C.

D.

E.

F.

a) Which conformation of 1,2-dichloroethane is the anti-staggered conformation? Explain.

D
b) Which conformation of 1,2-dichloroethane is the syn-eclipsed conformation? Explain.
C; torsi1,2-dichloroethane has the highest steric strain
c) Which conformation has the highest potential energy? Explain why.
C
d) Which conformation has the lowest potential energy? Explain why.
D
e) Which conformation has an equivalent energy to conformation A? Explain.
F
f) Which conformation has an equivalent energy to conformation E? Explain.
B
7. Draw cis and trans-1-2-dichlorocyclohexane in a chair conformation, and explain why both
chlorines must be axial or equatorial.
Ans:

8. Draw the structures of the cis-trans isomers for each compound. Label them cis and trans. If no
cis-trans isomers exist, write none.
a) 1,2 dimethylcyclopropane

b)

1,1-dimethyl-2-ethylcyclopropane (none)

c)

1,2-dimethylcyclohexane

d)

1,2,3-trimethylcyclopropane

cis-

trans-

9. Give an example and write the equation for the synthesis of an alkane through hydrogenation of
an alkene (pick an example).

10.

Write the equation for the formation of ethane from ethyl

halide through Grignard reagent.

Ans:
(EXAMPLE): The preparation of ethane through the hydrolysis of Grignard Reagent

CH3-CH2-Br + Mg > CH3-CH2-MgBr

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CH3-CH2-MgBr + H-OH > CH3-CH3 + MgBrOH

11.

Give the equation for the synthesis of n-butane

through Wurtz coupling reaction.

Ans:

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12. Give the equation for the synthesis of n-pentane from bromoethane through Corey-House
coupling reaction.

13. Chloromethane can be prepared by a reaction between methane and chlorine in the presence of
ultraviolet radiation. Outline the mechanism for this reaction.
Ans:

Chloroalkanes can be made from alkanes in a reaction known as a free radical substitution
reaction.
Eg

C2H6 + Cl2 C2H5Cl + HCl

A substitution reaction is one in which one atom or group of atoms on the organic molecule is
directly replaced by another. In this reaction the H atom on the alkane is replaced by a Cl atom.
In this reaction the free radical which starts the reaction is a chlorine atom, formed when a chlorine
molecule breaks up in the presence of ultra-violet light:
Cl2

Cl

Cl

Free radicals are represented by a dot next to the atom containing an unpaired electron. They are
caused by homolytic fission of covalent bonds.
Mechanism 1: free radical substitution
Free radical substitution reactions proceed in three stages: initiation, propagation and termination.
i)

Initiatation
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Most bonds do not undergo homolytic fission under normal conditions. Generally, UV light is
required.
UV
Cl2
Cl
Cl
ii)

Propagation
Propagation is the reaction of a free radical with a molecule to produce another free radical.
The reaction involves two propagation steps:

iii)

Termination
Termination is the combination of two free radicals to form a single molecule.

Cl

Cl2

Cl

TUTORIAL 2 ASC0303 ORGANIC CHEMISTRY

Alkenes and cycloalkenes
1. Give the IUPAC names of the following compounds:
CH3 CH3

a)
H3C

C
H

C
H

b)
C
H

C
H

CH3

CH3

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CH3

c)
H3C

C C
H2 H

d)
C
H

H3C

CH2CH3

CH2
CH2CH3

CH3

2. Name the following cycloalkenes.

3. Name each compound below using cis-trans system.

4. Draw all the possible isomers of the following:

a) C3H6 b) C4H8 c) C5H10
5. Write equations for the reaction of propene with:
a) hydrogen
b) chlorine
c) bromine
6. Write equations, using displayed formulae, to show the conversion of but-1-ene into:
a) butan-2-ol
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b) 2-bromobutane
c) 1,2-dibromobutane
d) propanal and methanal
7. Write equations for the reaction of hydrogen chloride with:
a) 1-butene
b) 3-hexene
8. Write equations for the reaction of KMnO4/hot H+ with:
a) 1-butene
b) 2-butene
9. Write equations for the reaction of 2- butane with:

a) Bromine water
b) KMnO4/NaOH
10. Write equations for the reaction of O3 and Zn/H+ with:
a) 1-butene
b) 2-methyl-2-butene
11. Write equations for the reaction of 1- butane with:
a) Hydrogen bromine
b) Hydrogen bromine/H2O2
12. Write equations for the reaction of water (in the presence of sulfuric acid)
a) propene
b) 2-butene
13.

Show the mechanisms for the following reactions:

a) ethene with bromine
b) 2-butene with hydrogen bromide
c) ethene with concentrated sulphuric acid
d) 2-butene with bromine water

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