3.3.

1 Introduction to organic chemistry

3.3.2 Alkanes

Student Question Pack

Text book pages 176 to 200

1
Task 1 Complete the following table for the first six alkanes:

Empirical Displayed Formula

Number Molecular Structural Formula Skeletal Formula
of Formula Formula
carbons
1

2
3
Task 2

a) Name the following compounds

b) Name or draw the following compounds:

Compound Skeletal formula

3-ethylpentane

2,3-dimethylpentane

3,3-dimethylpentane

2,2,3-trimethylbutane

4
 c) Name the following:

Skeletal formula Name

5
 d) Complete the following table
Name Displayed Skeletal
3-ethylhexane

2-methyl butane

Methyl propane

2,2-
dimethylpropane

2,3,3-
trimethylpentane

6
 e) Draw and name the following:

Skeletal formula Name

CH3CH2CH(CH3)CH3

CH3C(CH3)2CH2CH2CH3

CH3CH2CH(CH2CH3)CH3

CH3C(CH3)2CH(CH3)CH3

(CH3)3CC(CH3)2CH2CH3

 (CH3)3CCH(CH3)CH2CH3

 (CH3)3CCH(CH3)CH2CH3

(CH3)3CCH2CH(CH3)2

(CH3)2CHC(CH3)2CH2CH3

(CH3)2CHCH(CH3)CH(CH3)2

(CH3)3CC(CH3)3

f) Draw and name the following:

7
Structural formula Name

8
Task 3
Name the following:

a)

b)

c)

d) CH3CH(CH2CH3)CH(CH3)2

e) CH3C(CH3)2C(CH3)2C(CH3)2C(CH3)2CH3

f)

g)

h)

9
i)

j)

k)

l)

10
Task 4
a) Name the following compounds:
H Cl H
H C C C H

a. H H H

H Cl H
H C C C H

b. Cl H H

H Cl H
H C C C H

c. H Cl H

H Cl H
H C C C H

d. F H H

H Cl H
H C C C H
H H
e. CH3

H H H
H C C C Cl
H H
f. CH3

g.

h.

i. (CH3)2CHCH2Br

j. (CH3)2C(CH2CH3)CH2CHClCH3

11
Task 5
Draw the following compounds using displayed AND structural formulae:
1. Dichloromethane 3. 2-bromobutane

2. 1-chlorobutane 4. 3-ethyl-2-fluorohexane

12
Task 6
Draw the displayed formulae of the following compounds:
a) 2-iodobutane

b) 2-chloro-3-methylhexane

c) 3-bromo-2-chloroheptane

a) 1,2,3-trifluoropropane

b) 1,2,3,4,5-pentabromocyclopentane

c) 1,3-diiodo-4-methyl pentane

d) 1,1-dibromo-2,2-dichloropropane

13
e) 2,2-dichloro-4-ethylhexane

f) Triiodomethane

g) 1,1-dibromo-2-chloro-3,3,3-trifluoropropane

h) 1,2-dichloro-2-methylpropane

i) 3-chloro-2-methylbutanol

j) 4-methyl-3-chloro-pent-3-en-1-ol

14
Task 7 a) Draw the displayed and skeletal formulae of the following compounds:

Displayed Skeletal
Pent-2-ene

Hept-1-ene

Hept-3-ene

2-methyl hex-1-ene

Buta-1,3-diene

Octa-2-4-diene
Task 8 Name the following:

a)

b)

c)

d)

e) CH2=CHCH2CH(CH3)CH3

f) (CH3)2CHCH(CH3)CH2CH=CH2

g)

h) CH3CH2CH(CH3)CH=CHCH3

i)

- 16 -
 Task 9

a) Draw the following:

Name Structural Formula

2,3-dimethyl-1-butene

3,3-dimethyl-1-butene

2,3,3-trimethyl-1-butene

2,3-dimethyl-2-butene

b) Name the following

Skeletal formula Name

Task 10
- 17 -
Name or draw the following cyclic compounds:

Name Skeletal formula

Cyclohexane

Cyclohexene

Methylcyclohexane

3-methylcyclohexene

- 18 -
Task 11

a) Draw the following using skeletal formula:

1. Ethanol

2. Propan-2-ol

3. 2-methylpentan-3-ol

4. Ethane-1,2-diol

5. 3-methyl hexan-2-ol

6. Hexan-2,5-diol

7. pent-3-en-2-ol

- 19 -
b) Name the following:

a) CH2CHCH2CH(OH)CH3

b) CH3CH2CH2C(CH3)2OH

c)

d)

e)

f)

g) CH CH CH=CHCH CH OH
3 2 2 2

- 20 -
Task 12
1.
a. Pentane has the formula C5H12. Draw the displayed or skeletal formula of the molecule
in the space below.

b. Draw and name the chain isomers of C5H12.

2.
a. Hexane has the formula C6H14. Draw this molecule in the space below.

b. Draw and name the chain isomers of C6H14.

Task 13
- 21 -
 a) Draw and name the three possible positional isomers of pentanol:

b) How many different positional isomers can you make from octanol?

Task 14

1. Draw the functional group isomers of C4H9O.

2. Draw the functional group isomers of:

a) C2H6O

b) C3H6O2

- 22 -
 3. Pentane can react to form the following haloalkane Q.

State the type of structural isomerism shown by Q and the haloalkane shown below.

.............................................................................................................

Task 15
1. Draw the four structural isomers of C4H9Cl and name them.

2. Draw the three isomers of C4H8 containing a C=C bond and name them.

- 23 -
3. Draw the five structural isomers with the formula C6H14 in the correct boxes below and name them.

4. But-1-ene exists as isomers. Draw the following different types of isomer of but-1-ene.
Positional isomer

Chain isomer

Functional group
isomer

- 24 -
Task 16

The table shows 5 isomers.

1. Complete the table by giving the names of the isomers shown (4)
2. State the molecular formula of the isomers (1)
3. Isomer 6 is an alkene with the same molecular formula as the other isomers. Draw one possible
structure for this in the box and name it. (2)
4. Give the numbers of the isomers which show E/Z (or geometric) isomerism (3)

- 25 -
Task 17

1. Draw and name the E/Z isomers of 1,2-dichloropropene, CHCl=CClCH 3. If this compound exhibits
stereoisomerism isomerism, label the compounds as E or Z.

2. Draw and name the E/Z isomers of CH3CH=CHCH2CH3. If this compound exhibits
stereoisomerism isomerism, label the compounds as E or Z.

3. The following skeletal formulae show the stereoisomers of but-2-ene. Name each isomer (E/Z).

- 26 -
Task 18, part 1
Draw following molecules. Identify which exist as stereoisomers, those that do exist as stereoisomers
draw and name them by labelling the E/Z structures.
1. 1,2-dichloro 1,2-diiodo ethane

2. 1-bromo-2-fluoro prop-1-ene

3. 1,1 dichloro prop-1-ene

4. 1,2 dichloro prop-1-ene

5. 1,3 dichloro prop-1-ene

6. Prop-1-en-1-ol

7. 2 chloro prop-1-en-1-ol

Task 18, part 2

- 27 -
For the following alkenes; draw the structure, decide if it shows stereoisomerism (exists as E/Z isomers)
then draw the E/Z isomers.

- 28 -
Task 19, Multiple choice questions

1. Two isomeric forms of a saturated hydrocarbon

a. have the same structure.
b. have different compositions of elements.
c. have the same molecular formula.
d. have a different content of the isotopes of hydrogen.
e. react vigorously with one another.

2. Which of the following hydrocarbons does not have isomers?

a. C7H16
b. C6H14
c. C5H10
d. C4H8
e. C3H8

3. The name of the alkane isomer of cis-3-hexene is:

a. 2-methylpentane
b. 3-methylpentane
c. n-hexane
d. 2,3-dimethylbutane
e. cyclohexane

4. For which of the compounds below are cis-trans isomers possible?

CH3CH=CH2 CH3CH=CHCH2CH3 CH3CH=CHCH3
(1) (2) (3)

a. only 2
b. both 1 and 2
c. both 2 and 3
d. all three
e. only 3

- 29 -
5. Which of the following does NOT exhibit geometric isomerism? (Hint: draw them!)
a. 4-octene
b. 2-pentene
c. 3-hexene
d. 2-hexene
e. 1-hexene

6. How many isomeric alkanes of the molecular formula C5H12 are there?
a. 1
b. 2
c. 3
d. 4
e. 5

7. How many alcohols are structural isomers with the formula: C5H11OH?
a. 5
b. 6
c. 7
d. 8
e. 9

8. What is the relationship between the structures shown?

a. structural isomers
b. stereoisomers isomers
c. identical compounds

- 30 -
Task 20
Complete the table:
Compound Molecular Boiling Physical State at Room
Point/ºC
Formula Temperature / 1 atm.

Ethane -88.5
Propane -42.0
Butane -0.4
Pentane 36.2
Hexane 69.1
Heptane 98.5

1. Using the previous table, how does the boiling point change with the number of carbon atoms
present?

2. What type of intermolecular force is present in alkanes?

3. Explain why the boiling point increases with increasing carbon chain length in terms of these
intermolecular forces.

- 31 -
4. Branching is another factor that affects boiling point.
Complete the following table showing the boiling points of pentane and isomers of pentane.

Alkane Molecular Structural Formula Boiling

Formula Point/ºC

Pentane C5H12 36

C5H12 CH3 28

CH3CHCH2CH3

dimethylpropane C5H12 10

Explain this decrease in boiling point with increasing branching in terms of intermolecular
forces.

- 32 -
Task 21

Arrange the alkanes that follow in order of increasing boiling point, and explain why their boiling points
vary this way.

a. Hexane, pentane and butane.

b. 2,2-Dimethylpropane, pentane and 2-methylbutane.

- 33 -