Carbon Compounds

1. Carbon compounds are compounds that contain carbon:

I.
Organic-obtained from living things like plants and animals
II.
Inorganic-do not contain carbon to carbon bonds such as CO 2
2. Carbon compounds can also be classified into:
I.
Hydrocarbon-contain only carbon and hydrogen
II.
Non-hydrocarbon-has other elements in it
3. Hydrocarbon is mainly from petroleum; a mixture of different molecular size hydrocarbons that can be separated through fractional distillation at different temperature.
Saturated
Single covalent bonds
between atom

Definition

Unsaturated
At least one double or triple
covalent bond

Structural
Formula

Homologous
Alkane
Alkene
Series
4. Each carbon atom must be bonded to other atoms with:
I.
4 single covalent bonds
II.
2 single covalent bonds + 1 double covalent bond
III.
2 double covalent bond
5. Homologous Series-groups of carbon compounds that have the following general characteristics:
I.
Have same functional group
II.
Can be represented by general formula
III.
Can be prepared by same method
IV.
Two consecutive members have difference in RAM of 14
V.
Physical properties change gradually as number of carbon atoms in a molecule increase
Homologous Series
Alkane
Alkene
Alcohol
Carboxylic Acid
Ester

General Formula
CnH2n+2
CnH2n
CnH2n+1OH
CnH2n+1COOH
CnH2n+1COOCnH2n+

Functional Group
-C-C-C=C-OH
-COOH
-COO-

Type of Carbon Compound

Saturated Hydrocarbon
Unsaturated Hydrocarbon
Non-hydrocarbon
General Formula

Hydrocarbons
Saturated
Alkane
CnH2n+2

Non-Hydrocarbons
Unsaturated
Alkene
CnH2n

Alcohol
CnH2n+1OH

Carboxylic Acid
CnH2n+1COOH

Esters
Cn-1H2n-1COOCnH2n+1

-C-C-

-C=C-

-OH

Cn-1H2n-2COOH
-COOH

-COO-

Physical Properties
Hydrocarbons
Alkane
Alkene
1-4 exist as gas
2-4 exist as gas
5-9 exist as liquid
5-9 exist as liquid
Not reactive due to strong More reactive dues to existence
single covalent bonds which of covalent bond between 2
need a lot of energy to break
carbon atoms where chemical
reaction occur
1. Consist of molecules
2. Bonded by covalent bond
3. Held together by weak Van der Waals force of attraction
4. Insoluble in water
5. Soluble in organic solvents
6. Cannot conduct electricity
7. Low melting and boiling points
8. Less dense than water
9. -As number of carbon atoms per molecule increase,
-molecular size increase
-Van der Waals force of attraction increases
-more heat energy is needed to overcome the force
-melting and boiling point increase
- viscosity and density increases
-flammability/combustibility decreases
1-4 exist as gas
2-4 exist as gas
5-9 exist as liquid
5-9 exist as liquid

Alcohol
1 to 11 carbon exists as liquid
1. Methanol, ethanol and
propanol mix with water at
all proportions
2. Solubility in water
decreases with increasing
of molecular size
3. Low boiling points
4. Boiling point of alcohol
increases with increasing
number of carbon atoms
5. Ethanol is colourless, less
dense than water and
boiling point is 78C at 1 atm

Non-Hydrocarbons
Carboxylic Acid
1. Soluble in water
2. Ionises partially in water to
form weak acid
3. As number of carbon atom
per molecule increase:
- solubility decreases
- boiling point and
density increases

Esters
Neutral compound
Sweet smell
Low density
Less dense than water
Insoluble in water
Colourless liquid at room
temperature
7. Volatile and evaporate
easily at room temperature
8. Covalent compound
1.
2.
3.
4.
5.
6.

Chemical Properties
Hydrocarbons
Alkane
Combustion
(a lot of heat energy released; suitable for fuel)

CnH2n+2+O2 CO2 + H2O

CnH2n+2+O2 C+CO2 + H2O
CnH2n+2+O2 C+CO+ CO2 + H2O
Substitution
Occurs when:
I.
Mixed with halogens
II.
In presence of sunlight (UV light) to break covalent bond
CH4 + Cl2 CH3Cl + HCl
CH3Cl + Cl2 CH2Cl2 + HCl
CH2Cl2 + Cl2 CHCl3 + HCl
CHCl3 + Cl2 CCl4 + HCl

Alkene
Combustion
(sootier flame due to higher percentage of carbon by mass)
CnH2n + O2 CO2 + H2O
CnH2n + O2 CO + H2O
CnH2n + O2 C + H2O
Addition
Hydrogenation Alkane (CnH2n+2)
Conditions
-180 C
- Nickel or platinum as catalyst
CnH2n + H2 CnH2n+2
HalogenationCnH2nX2
CnH2n + X2 CnH2nX2
Hydrogen Halide CnH2n+1X
CnH2n + HX CnH2n+1X
Hydration Alcohol (CnH2n+1OH)
Conditions
-300 C
Phosphoric acid as catalyst
60 atm
CnH2n + H2O CnH2n+1OH

Acidified KMn04 (Oxidation) CnH2n(OH)2

CnH2n+H2O + [O] CnH2n(OH)2
Polymerisation

Alcohol +
Combustion
(burn with a blue flame without soot and release large amount of
heat; suitable as fuel)
CnH2n+1OH + O2 CO2 + H2O

Non-Hydrocarbons
Carboxylic Acid =
Cn-1H2n-2COOH +Metal
Cn-1H2n-2COOHMetal (Carboxylate Salt) +
H2
Cn-1H2n-2COOH+Base
Cn-1H2n-2COOHMetal (Carboxylate Salt)
+H2O

Cn-1H2n-2COOH+Metal Carbonate
Cn-1H2n-2COOHMetal (Carboxylate Salt)
+H2O + CO2

Cn-1H2n-2COOH+ CnH2n+1OH
Cn-1H2n-1COOCnH2n+1 + H2O

Esters
Esterification
Carboxylic Acid + Alcohol = Ester + Water
Cn-1H2n-2COOH+ CnH2n+1OHCn-1H2n-1COOCnH2n+1 +
H2O
1. 2 cm3 of glacial carboxylic acid is poured into a
boiling tube.
2. 4 cm3 of alcohol is added to the glacial carboxylic
acid.
3. Five drops of concentrated sulphuric acid are
added to the mixture with dropper. The mixture is
shaken.
4. Mixture is heated gently over a small flame until it
boils for 2-3 min.
5. Content is poured into a beaker half-filled water.
6. The odour, colour and solubility of the product are
recorded.
Observation
-Colourless liquid with sweet smell is formed.
-Liquid is insoluble in water.
-Liquid is less dense than water.

Dehydration Alkene
CnH2n+1OHCnH2n + H2O
Using catalyst such as:
- Porcelain chips
- Aluminium oxide
- Concentrated H2SO4 at 180C
- Concentrated H3PO4 at 210C

1. Place some glass wool in a boiling tube.

2. Pour 2cm3 of ethanol into boiling tube to soak the glass wool.
3. Some porcelain chips are placed in the middle of section of
the boiling tube.
4. The porcelain chips are heated strongly. The glass wool is
then warm gently so that ethanol vaporises and the vapour is
passed through the heated porcelain chips.
5. Collect the gas released in the two test tubes.
6. Test the gas with a lighted wooden splinter and bromine
water.
Observation
-Colourless gas is collected in test tube
- Gas burns with sooty flame
- Brown bromine water turns colourless

Oxidation of AlcoholCarboxylic Acid

Using oxidizing agents:
- Acidified potassium manganate (VII)
- Acidified potassium dichromate (VI)
CnH2n+1OH + 2[O] Cn-1H2n-2COOH + H2O
Reflux Method
-Liebig condenser is to prevent ethanol loss from
vaporisation

1. Pour 2cm3 of potassium manganate (VII) solution

into a boiling tube.
2. Add 10 drops of concentrated H2SO4
3. Heat gently.
4. Add 1cm3 of ethanol drop by drop into tube.
5. Delivery tube is connected. Mixture is heated until
it boils.
6. Distillate is collected and tested with blue litmus
paper.
7. Steps 1-6 are repeated by replacing with acidified
potassium dichromate (VI).
Observation
- Litmus paper turns red
- Distillate smells like vinegar
- APM turns from purple to colourless
- APD turns from orange to green
8. Pour 2cm3 of potassium manganate (VII) solution
into a boiling tube.
9. Add 10 drops of concentrated H2SO4
10. Heat gently.
11. Add 1cm3 of ethanol drop by drop into tube.
12. Delivery tube is connected. Mixture is heated until
it boils.
13. Distillate is collected and tested with blue litmus
paper.
14. Steps 1-6 are repeated by replacing with acidified
potassium dichromate (VI).
Observation
- Litmus paper turns red
- Distillate smells like vinegar
- APM turns from purple to colourless
- APD turns from orange to green

Chemical Tests to Differentiate Between Saturated and Unsaturated Hydrocarbons

Chemical
Properties
Sootiness of
flame

Reaction
with bromine
water

Reaction
with acidified
potassium
manganate
(VII) solution

Procedure

Observation
Alkane
Alkene
Burns with a yellow
Burns with a yellow
flame
and very sooty
Less soot collected
flame
More soot collected

Explanation

1. 2 cm3 of alkane and alkene is poured into two separate

porcelain dishes.
2. A lighted wooden splinter is used to light up the two liquids.
3. When the burning occurs, a piece of filter paper is held
above each flame.
4. The flame is observed for its sootiness and the amount of
soot collected on the filter paper is recorded.
1. 2 cm3 of alkane is poured into a test tube.
2. 2-3 drops of bromine water are added to alkane.
3. The mixture is shaken.
4. All changes that occurred is recorded.
5. Steps 1 to 4 is repeated with alkene to replace alkane.

No change

Brown colour of
bromine
decolourises

Alkene reacts with bromine at

double covalent bond to form
dibromoalkane
CnH2n + X2 CnH2nX2

1. 2 cm3 of alkane is poured into a test tube.

2. 2-3 drops of acidified potassium manganate (VII) solution
are added to alkane.
3. The mixture is shaken.
4. All changes that occurred is recorded.
5. Steps 1 to 4 is repeated with alkene to replace alkane.

No change

Purple colour
decolourises

Alkene reacts with solution at

double covalent bond.
CnH2n+H2O + [O] CnH2n(OH)2

Alkene contains higher

percentage of carbon by mass
than alkane

IUPAC Nomenclature
Hydrocarbons
Alkane
Alkene
Branch gets smallest number Carbon with double bond gets the
smallest number

Alcohol
Carbon closest to hydroxyl
functional group (-OH) gets
smallest number

PREFIX STEM SUFFIX

PREFIX STEM FG SUFFIX PREFIX
2,3pent
ane
2,3but
-1ene
2,4dimetyl
dimetyl
dimetyl
1. Identify longest carbon chain and no of carbon atoms to find stem
2. Identify carbon number with functional group
3. Identify branch chain (methyl or ethyl) and carbon number of branch
4. Identify suffix (-ane, -ene, -ol, -oic)
5. Write like following:
-number and number write (,)

STEM
but

FG
-2-

SUFFIX
ol

Non-Hydrocarbons
Carboxylic Acid
Carbon closest to carboxyl
functional group gets smallest
number
-COOH is always at the first
or last carbon, hence no FG
PREFIX
STEM SUFFIX
2-methyl
butan
oic

Esters
NAME
Alcohol
C. Acid
Methyl
Methanoate
Ethyl
Ethanoate

MOLECULAR FORMULA
C. Acid
Cn-1H2n-1COO

Alcohol
CnH2n+1

-number and name (-)

-name and name write close together
Isomerism
Isomers
How to
Construct
Isomer

Facts

Definitions

Alkane
Butane-2
Pentane-3
Change position
carbon

Alkene
Butene-3

Change position of
double bond
Change position of
carbon
Isomers have similar chemical properties but
different physical properties
Number of isomers increases as number of atom
per molecule increases
Molecular formula-shows type and number of
atoms in molecular compound
Structural formula-shows type, number of atoms
and how the atoms are bonded
Isomerism- a phenomenon where a compound has
same molecular formula but different structural
formula

Hydrocarbons
Alkane
Methane is
combustible and can
cause fire in landfills
and peat swamps

of

Alcohol
Propanol-2
Butanol-4
Change position
hydroxyl group
Change position
carbon

Alcohol
Preparation of Alcohol
Laboratory
- Fermentation- microorganisms such as yeast
acts on carbohydrates to form ethanol and
carbon dioxide
- Yeast added to glucose solution and left in warm
places without oxygen.
- Yeast contains zymase enzyme which breaks
glucose into ethanol and carbon dioxide
- Ethanol is purified by fractional distillation
- C6H12O6 2C2H5OH + 2CO2
Industrial
- Hydration of ethene
- 300C, phosphoric acid as catalyst and 60 atm
- CnH2n + H2O CnH2n+1OH

of
of

Non-Hydrocarbons
Carboxylic Acid
Uses of Carboxylic Acid
Carboxylic
Uses
Acid
Methanoic
Coagulate latex
Manufacture synthetic leather,
dyes and insecticide
Ethanoic
Food flavour and preservative
Drugs like aspirin
Citric
Flavouring in soft drink
Antioxidants
Fatty
Soap

Esters
Uses of Esters
Cosmetics and perfume
Artificial flavouring
Polyester
Soap
Fragrance
Name
Ethyl
butanoate
Methyl
butanoate
Pentyl
ethanoate

Source
Pineapple
Apple
Banana

Uses of Alcohol
Organic solvent and antiseptics
Fuel
NonHydrocarbons
Fats

Explanation

Fat and oil are natural esters formed through esterification (glycerol +
fatty acid; long chain carboxylic acid)
FAT
OIL
Saturated
Unsaturated
Solid at room temp
Liquid at room temp
From animals and human tissue
From fish tissue and plants
Butter, cheese
Peanut oil, soybean oil

Importance:
Energy
Build cell membrane and hormones
Dissolve certain vitamins for absorption
Saturated and unsaturated fats
Saturated fats are ester of saturated fatty acid (has single covalent
bonds only)
Unsaturated fats are esters of unsaturated fatty acids (has single and
double covalent bonds)
Fat/Oil is mixture of both saturated and unsaturated fat molecules
It is saturated if saturated molecules are more than unsaturated and
vice versa
Conversion of unsaturated fats to saturated fats
Easy oxidation of unsaturated fats causes it to turn rancid
Conversion occurs through hydrogenation with nickel as catalyst at 180
C in production of margarine

Effect of Fats on Health

LDL Cholesterol
Causes plaque deposit on walls of
vessels causing stroke and heart
attack
Animal fat (Saturated fats)
Butter, cheese

HDL Cholesterol
Reduces deposit on artery

Vegetable oil (Unsaturated fats)

Peanut oil, soybean oil

Palm Oil
From fresh oil palm fruits
49% saturated fats and 51% unsaturated fats
Used in cooking, manufacture of margarines, shortening etc
Advantages:
Rich in vitamin E (powerful antioxidant)
Rich in beta-carotene (vitamin A)
Cholesterol free

NonHydrocarbons
Natural
Rubber
(Polyisoprene
)

Explanation

Natural polymer of isoprene, C5H8 (polyisoprene) through

polymerisation
Latex
Milk like liquid obtained from tapped rubber tree.
Colloid which contains suspension of rubber particles in water.
Rubber particles made up of long chain rubber polymers surrounded
by protein membrane.
Protein membrane is negatively charged causing repulsion preventing
coagulation
Properties and Uses of Natural Rubber
Can be improved through vulcanization
Property
Description
Uses
Elasticity
Returns back to original shape once Rubber tube,
stretching force released
gloves,
rubber band,
shoe soles
Resistance to
Easily oxidised due to double bond
Limits usage
Oxidation
of natural
Effect of Heat
Heated-soften and becomes sticky
rubber
Cooled-hard and brittle
Effect of
Soluble in organic, alkaline and
Solvent
acidic solution
Vulcanisation of rubber

Sulphur heated together with natural rubber

Rubber stripe is soaked in sulphur monochloride solution in
methylbenzene solution for a few hours and then dried
The sulphur atom forms a cross-link between long rubber molecule
Reduces the ability of the polymers to slide over each other
Rubber molecules return to their original shape

Coagulation
Occurs when:
Acid is added to it
Left aside for 1-2 days due to
bacterial action on latex which
produces lactic acid (H+ ions)
-

Positively charged H+
neutralises negative charges
of protein membrane.
Neutral particle is formed.
No longer repel each other.
Collide with each other.
Protein membrane breaks.
Rubber polymers are freed.
Coagulate by combining
together to form a large lump
of rubber polymer. Latex has
coagulated.

Property
Elasticity

Resistance
to Oxidation

Prevention of Coagulation
Adding ammonia (alkali) to
neutralise acids produced by
bacteria

OH- from alkali neutralises H+

produced by acid as a result of
bacterial attack on protein.
No hydrogen ions.
Protein membrane remains
negatively charged.
Rubber particles repel each
other.
Rubber polymers cannot
combine and coagulate.

Natural Rubber
Less, polymer chain can
easily slide one over
another
Easily oxidized, presence
of double bond

Vulcanised Rubber
More, sulphur cross-links
prevents sliding
Not easily oxidized,
reduced number of double
bonds

Resistance
to Heat
Strength and
Hardness

Cannot withstand, easily

melt
Weaker and softer,
polymer chain can break

Can withstand, presence

of sulphur cross-links
Stronger and harder due
to sulphur cross-links

CHEMISTRY SPM Reactions Condition

Product
Catalyst
Temperature (C)
Pressure (atm)
Equation

Product
Catalyst

Contact Process
Sulphuric Acid
Vanadium (V) Oxide
450-500
2-3
2SO2 + O2 2SO3

Haber Process
Ammonia
Ferum
400-500
200
3H2 + N2 2NH3

Ostwald Process
Nitric Acid
Platinum
-

Oxidation of Alcohol

Dehydration of
Alcohol
Alkene
- Porcelain
chips
- Aluminium
oxide
- Concentrated

Esterification

Hydrogenation

Ester
Sulphuric Acid

Margarine
Nickel

Carboxylic Acid
Acidified potassium
manganate (VII)
Acidified potassium
dichromate (VI)

Hydrogenation
Alkane
Nickel or Platinum
180
CnH2n + H2 CnH2n+2

Hydration
Alcohol
Phosphoric acid
300
60
CnH2n + H2O CnH2n+1OH

Polymerisation
Polyalkene
200
1000

Temperature (C)
Pressure (atm)
Equation

H2SO4 at
180C
Concentrated
H3PO4 at 210C
180

CnH2n+1OH + 2[O]
Cn-1H2n-2COOH + H2O