Chapter 2 Carbon Compounds

Carbon Compounds

Organic Compounds
- of things/ compounds Inorganic Compounds
derived or obtained from things - not of living things
-

e.g. a) Carbohydrates, fats, amino acids,

e.g. carbon dioxide, ..;
proteins, vitamins, hormones, enzymes
carbon monoxide, .;
b) Petroleum and gas
calcium carbonate, ..

Hydrocarbons
1. Definition: Hydrocarbons are organic compounds that contain . carbon, C and
hydrogen, H.
2a) Hydrocarbons that contain only single covalent bonds are hydrocarbons.
The carbon, C atoms have the maximum number of hydrogen, H atoms possible.
b) Hydrocarbons that contain double or triple covalent bonds are .
hydrocarbons. The carbon, C atoms have fewer hydrogen, H atoms.
3. Main source: natural gas and petroleum ( a mixture of hydrocarbons).

Organic compounds

Hydrocarbons Non-hydrocarbons

A,

c.. a.,
hydrocarbons
hydrocarbons esters

Alkane Alkene, alkyne

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ALKANES
1. General formula: CnH2n+2, where n=1,2,..

2. Saturated hydrocarbons.

3. Simplest alkane: methane, has only one carbon atom.

Molecular formula: CH4.

Structural formula:

[A structural formula shows how atoms are bonded to each other in a molecule].

4. Naming alkanes (for straight-chain alkanes):

Stem meth eth prop but pent hex hept oct non dec
No. of C atoms 1 2 3 4 5 6 7 8 9 10
Suffix: ane.

Name of alkane n Molecular formula Structural formula

Methane 1 CH4

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5. Physical properties of alkanes:
Name of Molecular Relative Melting and Density Physical
alkane formula molecular boiling point (g cm-3) state at
mass (0C) room
temperature
Methane CH4 16 -182; -162 - Gas
-183; -89 -
-188, -42 -
-138; -0.5 -
-130; 36 0.63
-95; 69 0.66
-90; 98 0.68
-57; 126 0.70
-54; 153 0.72
-30; 174 0.73

a) The first four members of alkanes exist as . Pentane to C15H32 are .

b) Alkanes have low m.p and b.p. as the alkane molecules are held together by weak
. forces called . forces.

When the number of carbon atoms per molecule increases, the molecular size increases.

The van der Waals forces become stronger and more heat energy is needed to overcome the
intermolecular forces. Thus, the m.p and b.p. of alkanes increase.

c) Low densities of less than 1.00 g cm-3. Liquid alkanes .. on water.

d) Alkanes are insoluble in . but are soluble in .

Chemical Properties of Alkanes

1. Alkanes are generally unreactive because the covalent bonds in the molecules are very
strong.

2. Combustion
a) Alkanes burn readily in excess oxygen to produce and .. only.
Eg. : CH4 + 2 O2 CO2 + 2 H2O

Ethane:

Propane:

Butane:

b) Combustion of alkane is incomplete when there is insufficient oxygen. A mixture of

carbon (soot), carbon ., carbon dioxide and water vapour is produced.

c) Large alkane molecules are less flammable, and the flame becomes more ..
because the percentage of carbon increases.

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3. Substitution reactions: the hydrogen atoms of the alkane are replaced with chlorine, Cl or
bromine, Br atoms.

a) Chlorination of methane

Sunlight or ultraviolet light starts off the reaction by breaking up the halogen molecules.

Step 1: CH4(g) + Cl2 (g) CH3Cl(g) + HCl(g)

chloromethane

Step 2: CH3Cl(g) + Cl2 (g) CH2Cl2 (g) + HCl(g)

dichloromethane

Step 3: CH2Cl2 (g) + Cl2 (g) .. (g) + HCl(g)

Step 4: . (g) + Cl2 (g) .... (g) + HCl(g)

ALKENES
1. General formula: CnH2n , n = 2, 3, .

2. Unsaturated hydrocarbons. Their carbon atoms are held together by single and

covalent bonds.

3. Simplest alkene: ethene, C2H4 has two carbon atoms.

4. Naming alkenes:
Name of alkene n Molecular formula Structural formula

Chemical Properties of Alkenes

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1. Combustion
a) Alkenes burn in excess oxygen to form .. and .. .
[Write the chemical equations for the combustion of ethene and propene.]

b) Alkenes burn with a flame. The flame is more smoky than the corresponding
alkane. Eg. The combustion of hexene produces a more smoky flame than hexane because the
.. by mass of in hexene is higher than that of hexane.
Percentage of C in:
i) hexene, C6H12 (ii) hexane, C6H14

2. The functional group of alkenes is the .. bond between carbon atoms. Alkenes are
chemically . reactive than alkanes. Alkenes tend to undergo addition reactions which
are reactions in which atoms or groups of atoms are added to each carbon atom of the carbon-
carbon double bond.

- C=C - + X-Y -C C

X Y
(unsaturated) (saturated)

a) Hydrogenation
nickel or platinum
C3H6 (g) + H2 (g) C3H8 (g)
2000C

[Write the structural formula for the equation.]

Hydrogenation is used to make from vegetable oils.

b) Halogenation
When ethene is bubbled through a solution of bromine in water or in tetrachloromethane, the
reddish-brown bromine is decolourised immediately and a colourless liquid is formed.

Chemical equation:

[Write the structural formula for the equation.]

c) Addition of hydrogen halides

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Alkenes react with hydrogen chloride, HCl, hydrogen bromide, HBr and hydrogen iodide, HI at
room temperature to form halogenoalkanes.

Chemical equation:

[Write the structural formula for the equation.]

d) Addition of water (Hydration)

Alkenes do not react with cold water under ordinary conditions. When a mixture of ethene and
steam is passed over the catalyst phosphoric acid, H3PO4 at 3000C and a pressure of 60
atmospheres, ethanol is produced.

Chemical equation:

[Write the structural formula for the equation.]

e) Addition of hydroxyl groups

When an alkene reacts with acidified potassium manganate (VII) solution, KMnO4 the purple
colour of the solution is decolourised immediately. The product is a colourless organic compound
called a diol.

Chemical equation:

[Write the structural formula for the product.]

Chemical tests for the presence of a carbon-carbon double bond

Reagents which can be used to distinguish between unsaturated compounds and saturated
compounds are:
i)

ii)
3. Polymerisation

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A polymer is a large or long chain-like molecule made up of smaller molecules (called
..) that are joined together.

... is the process of chemically joining small molecules to form a polymer.

When alkene monomers join together to form a polymer, the process is called an

..

(i) Ethene molecules join together to form polythene. The process takes place at temperatures of
1000C to 3000C and under a pressure of 100 atm.

Chemical equation:

[Write the structural formula for the equation.]

(ii) Propene molecules join together to form .

Chemical equation:

[Write the structural formula for the equation.]

Polythene is a non-biodegradable substance used to make plastic .. and bottles.

Homologous Series
A homologous series is a group of organic compounds in which each member differs from the
next one by a fixed unit of structure. Example: and . are two different
homologous series.
a) Members of the same series can be represented by a general ...

b) Successive members differ from each other by ...

c) properties vary in a predictable way with increasing number of carbon atoms

per molecule.

d) Members have similar properties because they have the same functional group.

e) Members can be .. by similar methods

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Isomerism
Isomers are compounds with the same .. formulae but different
formulae.

. is the phenomenon of organic compounds existing as isomers.

Naming isomers:

Prefix stem suffix

tells the side-chains tells the no. of C atoms tells the
- alkyl groups, CnH2n+1 or R in the longest chain homologous
series

Practice:
Give the structural formulae and names of all the isomers of the following:
Structural Formula Name according to IUPAC
1(a)
C4H10

(b)
C5H12

2(a)
C4H8

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 (b)
C5H10

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Alcohols

1. General formula: ......................................

2. Functional group: .....................................

3. Naming alcohols:
Molecular Structural formula Condensed structural Name of isomer
formula formula

4. Making alcohols:
a) Industrial production of ethanol (Hydration of ethene)
......................... and ......................... react together at 3000C and 60 atmospheric pressure,
with ....................................... .............. as the catalyst.
Chemical equation:

[Write the structural formula for the equation.]

b) Preparation of ethanol in the laboratory

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Carbohydrates containing glucose, C6H12O6 such as rice or f................ are fermented. The
enzyme .......................... in yeast acts as the catalyst.
Chemical equation:

The ethanol that is produced is purified through ................................................. .

Physical Properties of Ethanol

- clear and colourless liquid.

- very v..................... because its boiling point is only 780C.
- very m............................. with water.

Chemical Properties of Ethanol

1. Combustion
Ethanol is very flammable, burns with a non-smoky flame. Complete combustion
produces ..., . and a large amount of ...
Chemical equation:

2. Dehydration (removal of water)

- H2O
Ethanol Ethene

Chemical equation:

Method:
a) Ethanol vapour is passed over a heated catalyst such as . .
chips, .. pot or ., Al2O3.

Diagram:

b) Ethanol is heated at 1800C with excess concentrated sulphuric acid.

The ethene produced can be tested:

a) It . reddish-brown .
b) It ... acidified solution.
3. Oxidation
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Alcohols are oxidized to carboxylic acids by oxidizing agents such as . ...
.... solution and . .. solution.

a) When acidified .. solution is used, it turns from .. to

b) When acidified .. . solution is used, the . solution is

Uses of alcohols:

Carboxylic Acids
1. General formula: .
2. Functional group:
3.
n Molecular Formula Structural Formula Name

4. Preparation of ethanoic acid in the laboratory: ethanol is oxidized by an excess of acidified

potassium dichromate (VI) solution. The mixture of ethanol, potassium dichromate(VI) solution
and concentrated sulphuric acid is heated under reflux.

Chemical equation:

5. Physical properties of ethanoic acid

Physical state at Colour Smell Taste M.p. & B.p.

room temperature
16.60C & 1180C

Chemical Properties of Ethanoic Acid

Ethanoic acid is a weak acid.
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I Its reactions as an acid
Chemical equations:
a)

b)

c)

II Its reaction with alcohols (esterification).

Carboxylic acid + Alcohol Ester + Water

a) ethanoic acid + methanol

Equation:

Name of ester:

Structural formula:

b) ethanoic acid + butanol

c) methanoic acid + propanol

d) propanoic acid + ethanol

Esters
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1. General formula: ..

2. Functional group: .

3. Physical properties:
a)
b)

4. Uses:
a) Esters are used as artificial . or scents as they emit a sweet smell.
b) Esters are used in making artificial . that are added in many edible
items like ice creams, soft drinks, sweets, etc.
c) Esters are used as industrial solvents for making cellulose, fats, paints and varnishes.
d) Esters are used as solvents in pharmaceutical industries.
e) Esters are used as softeners in plastic industries and moulding industries

5. Preparation: reflux a mixture of alcohol, carboxylic acid and concentrated sulphuric acid.

Diagram:

Fats
Comparison of fats and oils:
Fats Oils
Source
Physical state at room
temperature
Melting point

Oils and fats are formed from carboxylic acids called .. ..

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and an alcohol called .. or ....

a) A fatty acid has a long chain of carbon atoms (about 10 to .. atoms), eg. palmitic acid,
CH3(CH2) 14COOH and oleic acid, CH3 (CH2) 7CH=CH(CH2)7COOH.
b) Glycerol is an alcohol with 3 hydroxyl groups.

fatty acid + glycerol oil or fat + water

5. Unsaturated fats can be converted to saturated fats through . . Hydrogen gas

is passed through unsaturated fat at 1500C to 2000C and the catalyst, .. is used.
This is the process used in making ..

Natural Rubber
1. Natural rubber is a natural polymer (very large molecules formed from smaller molecules
called ..). E.g. Starch (its monomer is ..) and protein (its monomer is ..
).
2. The monomers of natural rubber are . molecules which join together to
form .. .

Isoprene Polyisoprene
(2-methylbuta-1,3-diene)
3. Properties:
a) E. returns to its original shape after you stretch it.
b) Easily ... by oxygen which adds to the carbon-carbon double bond.
c) Cannot withstand . . When heated it becomes ... and ... . At low
temperature it becomes . and ....
d) Can be attacked by and solvents.

Coagulation of Latex
1. Latex is a milk-like .... which is a mixture of rubber particles suspended in ...
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2. A rubber particle is made up of a protein membrane that surrounds many rubber
(p....) molecules.
3. Latex coagulates when dilute .. are added to it. Coagulation of latex is the
separation of rubber particles from the ... in the latex.

a) The protein membrane is

charged. Therefore,
rubber particles .. each
other. The latex does not
coagulate.

b) The hydrogen ions, H+ from

acids neutralize the .
charges.

c) The rubber particles no longer

repel each other. They ..
with each other. This breaks the
.. . The
molecules are now free.

d) The rubber molecules

.. together. The latex
has coagulated.

4. Fresh latex left for some time will eventually coagulate because . In the
latex will produce acid.
5. . can neutralize these acids. is usually added to
prevent latex from coagulating.
Vulcanization of Rubber
1. Natural rubber is elastic because when it is stretched, its molecules over each
other. If rubber is over-stretched, the molecules can no longer return to their original position
and the rubber loses its elasticity.
2. Vulcanization is the process of treating natural rubber with .. to make it more
elastic and stronger. The treated rubber is called rubber.
3. The sulphur atoms form . between the rubber molecules which prevent
rubber molecules from sliding too much when stretched. The rubber molecules return to their
original positions after being stretched.

Diagram:

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SPM 2006 Paper 3
Diagram 2 shows the stretching phases of a vulcanized rubber strand and an unvulcanised
rubber strand.
Stretching phases Length of vulcanized rubber Length of unvulcanised rubber
Before

45 mm
45 mm

During

5960mm
mm

After
45 mm
50 mm

Diagram 2
Plan an experiment to compare one characteristic shown in Diagram 2 for both types of rubber.
Your planning should include the following aspects:
(a) Problem statement
(b) All the variables
Hypothesis
(d) List of materials and apparatus
(e) Procedure of the experiment
(f) Tabulation of data

Exercise

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Member Molecular formula Molar mass (g mol-1) Boiling point (0C)

1 -104

2 -48

3 -6

4 30

The table shows the boiling points of the first four straight-chain alkenes.

a) What is the general formula of the alkene homologous series? ..............................................

b) Complete the above table. [H,1; C,12]

c) Draw the structural formula of the second member.

d)(i) What is the physical state of the fourth member at room conditions? ................................

(ii) How do the boiling points of the alkenes change with increasing number of carbon
atoms per molecule? Explain.

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

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

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

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

e) E is also a straight-chain alkene. Its molar mass is 98. Calculate the number of carbon
atoms in an E molecule. [H,1; C,12]

f) Write the chemical equation of the complete combustion of the fourth member.

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

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