CHAPTER

2
Carbon
Compounds
 2.1 Carbon
Compounds
• Carbon compounds:
Compounds that contain carbon as one of
their constituent elements
 Carbon compounds

Organic compounds Inorganic compounds

• Carbon-containing  Non-carbon-containing
compounds that can compounds that can be
be obtained from obtained from non-living
things
living things
 Include oxides of carbon,
• Except oxides of
carbonates, cyanides and
carbon, carbonates, metallic carbides
cyanides and metallic  Examples:
carbides
• Examples:
 Hydrocarbo
n
• Hydrocarbon:
Organic compounds which contains carbon and
hydrogen only
• Examples:
Petroleum, coal, natural gas, rubber tree
• Non-hydrocarbon:
Organic compounds containing carbon, hydrogen
together with a few other elements
• Examples:
Sugar
 Organic compounds

Hydrocarbons Non-
hydrocarbons
C and H C, H and O, N, P, S, F,
Cl, Br and I
Saturated Unsaturated
hydrocarbon hydrocarbon
 Contain only  Contain at least
single one multiple
bonds bonds
C C C C
C

C
Combustion products of organic compounds

• When an organic compound burnt in excess

oxygen, the main product are carbon dioxide,
CO2 and water, H2O

+ 6O2 → 6CO2 + 6H2O

C6H12O6
glucose
Akl anes, alkenes,
alcohols, carboxylic acd
is
and esters
 1. Molecular
formula
• Meaning
The formula that shows the actual numbers
and types of atoms present in a molecule.
Molecular formula Explanation
Propane, C3H8 Contains 3 carbon atoms and 8
hydrogen atoms
Pentane, C5H12 Contains 5 carbon atoms and 12
hydrogen atoms
 2. Structural
• formula
Meaning
The formula that shows how the atoms in a
molecule are bonded together and by
what types of bonds
Molecular formula Structural formula
Propane, C3H8
H H H

H C C C HH

H H
 3. Naming of carbon compound
(IUPAC)
• Guideline to naming the carbon compound:
Have 2 components

Show the number Show the family

of carbon atoms in of the compound
the molecules

Root Ending
 a) stem/root

Number of
carbon 1 2 3 4 5 6 7 8 9 10
atom

Stem Meth Eth Prop But Pent Hex Hept Oct Non Dec
b) suffix/ending
• Ending; different followed by the
homologous series
Homologous series Ending
Alkane ……ane
Alkene ……ene
Alcohol ……ol
Carboxylic acid ……oic acid
Ester ……yl ……..oate
 B.
ALKANES
Physical properties of alkanes
• Alkanes are covalent compounds which
consist of simple molecules
• Molecules are held together by weak
intermolecular force
 Solubility
• Dissolve in
organic solvents
• Insoluble in Melting and
Density
water boiling point
• Less dense than
water • Low melting
&
boiling
point
Electrical Physical state at
conductivity room
temperature
• Cannot conduct Physical
electricity properties of • C1 to C4 are
• Because there alkanes gases
are no free • C5 to C17 are
moving ions liquid
• C18 > are
solid
 Explain the effect of the increase in number of
carbon atoms in alkane molecules

Size of molecule increase

Melting point & boiling point increase

• The higher the number of carbon atoms, the
higher the melting & boiling point
• As the number of carbon atoms increases, the
molecule become bigger
• The force of attraction between the molecules
become stronger
• More heat energy is needed to overcome the
strong force of attraction between molecules
Why melting and boiling point propane is higher
than ethane?
• Propane have more number of carbon atoms per
molecule than ethane
• Size of propane is bigger than ethane
• The force of attraction between propane
molecule increase
• More heat energy is needed to overcome the
force of attraction between propane molecule
• So, melting and boiling point of propane is higher
than ethane
 Chemical properties of alkanes
Combustion
a) Complete combustion: produce CO2 + H2O
C2H6 + O2 → CO2 + H2O

b) Incomplete combustion: produce CO/C gas +

H2O
2CH4 + 3O2 → 2CO + 4H2O
CH4 + O2 → C + 2H2O
Halogenation
• Reactions of alkanes with halogens
• Take place readily in sunlight/ultraviolet
• Example of substitution reaction

Reaction that occurs when one

atom or a group of atoms in a
molecule is replaced by another
atom or group of atoms
• CH4 + Cl2 → CH3Cl + HCl

• CH3Cl + Cl2 →

• CH2Cl2 + Cl2 →

• CHCl3 + Cl2 →
 C.
ALKENES
Physical properties of alkenes are similar to
alkanes
• Molecules are held together by weak
intermolecular force
 Solubility
Density
• Dissolve in organic
• Less dense than
solvents
water
• Insoluble in water

Electrical
conductivity Melting and
• Cannot conduct boiling point
electricity • Low melting &
• Because there are
boiling point
no free moving Physical
ions properties of
alkenes
 Explain the effect of the increase in number of
carbon atoms in alkene molecules

Size of molecule increase

Melting point & boiling point increase

• The higher the number of carbon atoms, the
higher the melting & boiling point
Why melting and boiling point butene is higher
than ethene?
• Butene have more number of carbon atoms per
molecule than ethene
• Size of butene is bigger than ethene
• The force of attraction between butene molecule
increase
• More heat energy is needed to overcome the
force of attraction between butene molecule
• So, melting and boiling point of butene is higher
than ethene
 Chemical properties of alkenes
Combustion
(a) Complete combustion: produce CO2 + H2O
C2H4 + O2 → CO2 + 2H2O

(a) Incomplete combustion:

produce CO/C gas +
H 2O
C2H4 + 2O2 → 2CO + 2H2O
C2H4 + O2 → 2C + 2H2O
Hydrogenation
• Alkenes react with hydrogen at 180 °C at
presence of nickel/platinum (catalyst) to
produce alkanes

Ni, 180 °C
C2H 4 + H 2 C2H 6
Halogenation
• No catalyst or ultraviolet is needed
• Alkenes react with halogen at room
temperature in the presence of
tetrachloromethane, CCl4

C2H4 + Cl2 → C2H4Cl2

C4H8 + Br2 → C4H8Br2

Used to test for the presence of a carbon-
carbon double bond
Hydration
• Alkenes reacts with steam, H2O at 300 °C and
60 atm in the presence of concentrated H3PO4
(as catalyst) to produce alcohol
H3PO4
C2H 4 + H 2O C2H5OH
300 °C, 60 atm
Addition of hydrogen halides – HX
• Hydrogen halides: Hydrogen chloride, HCl or
hydrogen bromide, HBr
• Alkenes reacts with hydrogen halide, HX at
room temperature to produce haloalkane

C2H4 + HCl → C2H5Cl

Addition of hydroxyl group
• Alkenes react with acidified potassium
manganate(VII), KMnO4 to produce diol
compound

C2H4 + H2O + [O] → C2H4(OH)2

or
KMnO4
C2H4 C2H4(OH)2

Used to test for the presence of a carbon-carbon double bond

Polymerization reaction
• Small alkene molecules undergo an addition
reaction with one another at high pressure of
1000 atm and temperature 200 °C

H H H H

n H C C H C C
n
H H
 Compare & contrast alkanes with alkenes

• What do alkanes and alkenes have in

common?
• How do they differ from each other?
 Comparing chemical
properties
Reactivity
Procedure:
1. Pour 2 cm3 of propane and propene into each
crucible.
2. The liquids are lighted.
3. When burning occurs, filter paper is placed
on top of the flame.
4. All the observation is recorded.
Observation:
Propane:
Burn in air, producing yellow sooty flame
Propene:
Burn in air, producing yellow and a very
sooty flame

Conclusion:
Propene is more reactive than propane
Describe two chemical test to differentiate
between hexane and hexene
• Reaction with bromine water

Procedure:
1. Pour about [2-5 ] of hexane into a test tube.
2. Add 4-5 drops of bromine water and shake it.
3. Observe any changes and repeat with hexene.

Observation:
Hexane: Brown colour of bromine remains unchanged
Hexene: Brown colour of bromine decolourise/turn
colourless
• Reaction with acidified potassium manganate(VII) solution

Procedure:
1. Pour about [2-5 ] of hexane into a test tube.
2. Add 4-5 drops of acidified potassium manganate(VII)
solution and shake it.
3. Observe any changes and repeat with hexene.

Observation:
Hexane: Purple colour of KMnO4 remains unchanged
Hexene: Purple colour of KMnO4 decolourise/turn colourless
Determine which one is more soot between
hexane and hexene when burn in oxygen. Give
your reason.
Hexane, C6H14 Hexene, C6H12
= 6(12) x 100 = 6(12) x 100
[6(12)+14(1)] [6(12)+12(1)]
= 83.72% = 85.71%

Hexene has high percentage of carbon by mass than

hexane.
So, hexene burn with more sooty flame
 Density
Solubility
• Low density
• Slightly soluble in
water but readily Boiling point
dissolve in organic
solvent • Low boiling
point

Odour
State
Physical • Sweet pleasant
• Simple ester is
properties of smell (fruity
colourless liquid at
room condition ester smell)
 E.
ALCOHOL
Industrial production of ethanol
• Two main process:
(a) From sugar and starch by fermentation
(b) From petroleum fraction by hydration
 1. Fermentation
C6H12O6 → 2C2H5OH + 2CO2

• From sugar & starches

• Yeast added
• Left in warm place (absence of oxygen)-
anaerobic
Temperature = 18 – 20 °C
Catalyst = yeast
(zymase)
Other condition =
absence of oxygen
 2. Hydration
C₂H₄ + H2O → C2H5OH

• From petroleum fractions

Temperature = 300 °C
Pressure = 60 atm
Catalyst = phosporic
acid, H3PO4
 Chemical properties of alcohols
Combustion
(a) Complete combustion: produce CO2 + H2O

C2H5OH + 3O2 → 2CO2 + 3H2O

Oxidation reaction
• React with the oxidation agent:
a) acidified potassium manganate(VII), KMnO4
(purple → colourless)
b) acidified potassium dichromate(VI), K2Cr2O7
(orange → green)

C2H5OH+ 2[O] → CH3COOH + H2O

Ethanol Ethanoic acid
Dehydratio
• Removal of water molecule from alcohol
n
molecule
C2H5OH → C2H4 + H2O
Ethanol Ethene
• Method:
(a) Heated under reflux at 180 °C with excess
concentrated H2SO4 or
(b) Pass over a heated catalyst (porcelain chips,
porous pot, Al2O3
 Uses of alcohols
As a solvent in
•Perfumes, cosmetics, toiletries
As a thinner in
•Lacquer, varnish, shellac, ink
As a cleaner for
Compact disc, video cassette recorder head
As a fuel
• Clean fuel, biofuel, gasohol
As a raw material in manufacture of
• Vinegar, fibre, explosive, plastic
As a raw material to make pharmaceutical
products
• Tincture, antiseptic, cough syrup, rubbing
alcohol
 F. CARBOXYLIC
ACIDS
Functional group
• Carboxyl group ( -COOH )

General formula
• CnH2n+1COOH
 Solubility
• Simple molecules are
very soluble in water Colour
• Due to water molecule • Colourless
being strongly liquid
attracted to the – Boiling point
COOH group • High boiling
• Solubility ↓ when
point
number of carbon per
molecule ↑

State Physical Odour

• Larger molecules properties of • Sharp/unplea
(C10 above) are carboxylic sant smell
wax-like solids acids
Synthesised/making of ethanoic acids

Oxidation of alcohol

C2H5OH+ 2[O] → CH3COOH + H2O

Ethanol Ethanoic acid

• Reflux ethanol with acidified potassium

dichromate(VI) solution or acidified potassium
manganate(VII) solution
 Chemical properties
Acid properties
• CH3COOH is a weak monoprotic acid
• Only one hydrogen atom can ionize in water to
produce H+ ion
CH3COOH ↔ CH3COO- + H+
Ethanoic acid Ethanoate
ion

• Partially dissociate in water

• Turn moist blue litmus → red
• React slowly with metals, bases and
carbonates
Reaction with metals

Carboxylic acid + metal → salt + H2

2CH3COOH + Zn → Zn(CH3COO)2 + H2
Ethanoic acid Zinc ethanoate
Reaction with bases

Carboxylic acid + bases → salt + H2O

CH3COOH + NaOH → CH3COONa + H2O

Ethanoic acid Sodium
ethanoate

2CH3COOH + CuO → Cu(CH3COO) 2 + H2O

Ethanoic acid Copper
ethanoate
Reaction with carbonates

Carboxylic acid + carbonates → salt + CO2 + H2O

2CH3COOH + CaCO3 → Ca(CH3COO)2 + CO2 + H2O

Ethanoic acid Calcium
ethanoate
Reaction with alcohols

Carboxylic acid + alcohol → ester +

H2O

Catalyst: Concentrated H2SO4

CH3COOH + C4H9OH → CH3COOC4H9 + H2O

Ethanoic Butan-1-ol Buthyl ethanoate acid
 Uses of carboxylic acids
Ethanoic acid
• As a flavouring
• As a preservative
• Used with other chemicals to make drugs, dyes, paints,
insecticides and plastics
Methanoic acid
• Used to coagulate latex
Fatty acids (long-chain carboxylic acids)
•Used in making soaps
Benzoic acid
• Preservative in food
 G.
ESTER
Functional group
• Carboxylate group ( -COO- )

General formula
• CnH2n+1COOCmH2m+1
Naming ester
 Boiling point
Colour • Low boiling
• Colourless point
Solubility liquid at room compare to
temperature water
• Simple
alcohols are Odour
very
soluble in • Very sharp
water smell
• Because
has
State –OH group
• C1 to C11 are Physical
liquid at room properties of Highly
temperature alcohol volatile
 Formation of ester
Esterification reaction
• Catalyst: Concentrated H2SO4
 Natural sources
Fruit
Pineapple – C3H7COOC2H5
Ethyl butanoate

Flower
Jasmine – CH3COOCH2C6H5
Benzyl ethanoate
 Use of ester
• Preparation of cosmetics & perfumes
• Used as food additives (enhance the flavour &
smell of processed food)
• Production of soap & detergent