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CARBON

COMPOUNDS
Organic compounds
1. Hydrocarbons – organic compounds that contain hydrogen and carbon elements only.
2. Non-hydrocarbons – organic compounds that contain other elements (oxygen, nitrogen,
iodine, phosphorus)
3. Saturated hydrocarbons – only single bonded (Carbon-Carbon) hydrocarbons.
4. Unsaturated hydrocarbons – at least one double / triple bonded (Carbon-Carbon)
hydrocarbons.
5. Complete combustion – organic compounds burn completely which form CO 2 and H2O.
6. Incomplete combustion – organic compounds burn with sufficient supply of O 2 which
form C (soot), CO and H2O.

Homologous Series

Homologous series – is a group or family of organic compounds containing a particular


functional group and similar chemical properties

Carbon Compounds General Formula Functional group


Carbon-carbon single bond
Alkane CnH 2n+2 n = 1, 2, 3, …
-C–C-
Carbon-carbon double bond
Alkene CnH 2n n = 2, 3, 4, …
-C=C-
Hydroxyl group
Alcohol CnH 2n+1OH n = 1, 2, 3, …
- OH
Carboxyl group
Carboxylic Acids CnH 2n+1COOH n = 0, 1, 2
- COOH
n = 0, 1, 2, … Carboxylate group
Esters CnH 2n+1COOC mH2m+1
m = 1, 2, 3, … - COO -
IUPAC Nomenclature – used to name organic compound.

Prefix + Root + Suffix.

1. Prefix – name of the branch or side chain.

Formula Branch or name of group


CH3 - methyl
C2H5 - ethyl
C3H7 - propyl
C4H9 - butyl
C5H11 - pentyl

2. Two or more types of branches are present, name them in alphabetical order.

Number of side chain Prefix


2 Di-
3 Tri-
4 Tetra-
5 Penta-
6 Hexa-

3. More than one side chains are present, prefixes are used.
4. Root – the parent hydrocarbon (the longest carbon chain).

Number of carbon atoms Root name Number of carbon atoms Root name
1 meth- 6 hex-
2 eth- 7 hept-
3 prop- 8 oct-
4 but- 9 non-
5 pent- 10 dec-

o The longest continuous (straight chain) carbon chain is selected.


o Identify the number of carbon.
5. Suffix – functional group.

Homologous series Functional group Suffix


Alkane -C–C- -ane
Alkene -C=C- -ene
Alcohol – OH -ol
Carboxylic acid – COOH -oic
Ester – COO – -oate
Alkanes
1. General formula: C nH2n+2 . Where n = 1, 2, 3, … (n = number of carbon)

2. Alkanes are saturated hydrocarbon.

Name of alkane Molecular formula Name of alkane Molecular formula


Methane CH4 Hexane C6H14
Ethane C2H6 Heptane C7H16
Propane C3H8 Octane C8H18
Butane C4H10 Nonane C9H20
Pentane C5H12 Decane C10H22

3. Physical properties of alkanes

Name Molecular formula RMM Density(g cm-3) Physical state at 25°C


Methane CH4 16 - Gas
Ethane C2H6 30 - Gas
Propane C3H8 44 - Gas
Butane C4H10 58 - Gas
Pentane C5H12 72 0.63 Liquid
Hexane C6H14 86 0.66 Liquid
Heptane C7H16 100 0.68 Liquid
Octane C8H18 114 0.70 Liquid

Alkanes with more than 17 carbon atoms are solid.

 Solubility– insoluble in water but soluble in organic solvent


 Density – less dense than water
 Electrical conductivity –do not conduct electricity.
 Boiling and melting points –low boiling points and melting points.
4. Chemical properties of alkanes

 Combustion of alkanes
Complete combustion

CH4 + 2O2 –> CO2 + 2H2O

Incomplete combustion occurs when insufficient supply of oxygen

CH4 + O2 –> C + H2O


2CH4 + 3O2 –> 2CO + 4H2O

 Substitution reaction of alkanes (Halogenation)


Substitution reaction is one atom or a group of atoms in a molecule is replaced by another
atom or a group of atoms.

Example:
CH4 + Cl2 –> HCl + CH3Cl (Chloromethane)
CH3Cl + Cl2 –> HCl + CH 2Cl2 (Dichloromethane)
CH2Cl2 + Cl2 –> HCl + CHCl3 (Trichloromethane / chloroform)
CHCl3 + Cl2 –> HCl + CCl4 (Tetrachloromethane)
The rate of reaction between bromine and alkanes is slower than the rate of reaction
between chlorine and alkanes because chlorine is more reactive than bromine.
Alkene
1. General formula: C nH2n. Where n = 2, 3, 4 … (n = number of carbon)

2. Alkenes are unsaturated hydrocarbons

Name of alkene Molecular formula


Ethene C2H4
Propene C3H6
Butene C4H8
Pentene C5H10
Hexene C6H12
Heptene C7H14
Octene C8H16
Nonene C9H18
Decene C10H20

3. Physical properties of alkenes

Name Molecular formula RMM Density(g cm-3) Physical state at 25°C


Ethene C2H4 28 0.0011 Gas
Propene C3H6 42 0.0018 Gas
Butene C4H8 56 0.0023 Gas
Pentene C5H10 70 0.6430 Liquid
Hexene C6H12 84 0.6750 Liquid
Heptene C7H14 98 0.6980 Liquid
Octene C8H16 112 0.7160 Liquid
Nonene C9H18 126 0.7310 Liquid

 Solubility – insoluble in water but soluble in organic solvent


 Density – less dense than water.
 Electrical conductivity – do not conduct electricity.
 Boiling and melting points –low boiling points and melting points.
4. Chemical properties of alkenes

 Combustion of alkenes
Complete combustion

C2H4 + 3O2 –> 2CO2 + 2H2O


(Alkenes burn with sootier flames than alkanes. This is because the percentage of carbon
in alkene molecules is higher than alkane molecules)

Incomplete combustion occurs when insufficient supply of oxygen

C2H4 + O2 –> 2C + 2H2O


C2H4 + 2O2 –> 2CO + 2H2O
(The flame in the incomplete combustion of alkenes is more smoky than alkanes)

 Polymerisation reaction of alkenes


Polymerisation is the reaction when small molecules (monomers) are joined together to
form a long chain molecules (polymer).

n (CH 2 = CH2) –> -(- CH2 – CH2 -)-n

 Hydrogenation
Hydrogenation is the addition of hydrogen to alkenes

C2H4 + H2 –> C2H6 (catalyst: nickel/platinum and temperature: 180°C)

 Addition of halogen (Halogenation)


Halogenation is the addition of halogens to alkenes

C2H4 + Br2 –> C2H4Br2


In this reaction the brown colour of bromine decolourised to produce a colourless liquid.
Bromination is also used to identify an unsaturated

 Addition of hydrogen halides


Hydrogen halides are hydrogen chlorine, hydrogen bromide, hydrogen iodide and etc.

C2H4 + HBr –> C2H5Br (Bromoethane)

 Hydration
Alkenes can react with a mixture of alkene and steam pass over a catalyst (Phosphoric
acid, H3 PO4). The product is an alcohol.

C2H4 + H2O –> C2H5OH


 Additional of acidified potassium manganate(VII), KMnO 4
The purple colour of KMnO4 solution decolourised immediately to produce colourless
organic liquid. Also used to identify the presence of a carbon-carbon double bond in a
chemical test.

Comparing of Alkanes and Alkenes

Physical Properties Alkanes Alkenes


Physical state Physical state changes from Physical state changes from
gas to liquid when going down gas to liquid when going down
the series. the series.
Electrical conductivity Do not conduct electricity at Do not conduct electricity at
any state. any state.
Boiling points and melting Low boiling points and melting Low boiling points and melting
points points points
Density Low densities Low densities
Solubility Insoluble in water (soluble in Insoluble in water (soluble in
organic solvent) organic solvent)
Chemical Properties Alkanes Alkenes
Reactivity Less reactive Reactive
Combustion Burn in air and produce yellow Burn in air and produce yellow
sooty flame. and sootier flame compare to
alkanes.
Reaction with bromine solution No reaction. Decolourise brown bromine
solution.
Reaction with acidified No reaction. Decolourise purple acidified
potassium manganate(VII) potassium manganate(VII)
solution solution.

Isomerism
 Isomerism – existence of two or more compounds having the same molecular formula
but different structural formula
 Isomer – compounds exhibiting the same molecular formula but different structural
formula
Alcohol
1. General formula: C nH2n + 1OH. Where n = 1, 2, 3 … (n = number of carbon)

2. Alcohols are non-hydrocarbons which contain carbon, hydrogen and oxygen atoms.

Name of alcohol Molecular formula of alcohol


Methanol CH3OH
Ethanol C2H5OH
Propanol C3H7OH
Butanol C4H9OH
Pentanol C5H11OH
Hexanol C6H13OH
Heptanol C7H15OH
Octanol C8H17OH
Nonanol C9H19OH
Decanol C10H21OH

3. Physical properties of alcohol

Name Molecular Melting point (°C) Boiling point (°C) Physical state at 25°C
formula
Methanol CH3OH -97 65 Liquid
Ethanol C2H3OH -117 78 Liquid
Propanol C3H5OH -127 97 Liquid
Butanol C4H7OH -90 118 Liquid
Pentanol C5H9OH -79 138 Liquid

 Solubility – very soluble in water


 Volatility – evaporates easily at room temperature
 Colour and Smell – colourless liquid and have a sharp smell.
 Boiling and melting points – low boiling points
4. Chemical properties of alcohol

 Combustion of alcohol
Complete combustion of alcohol.

C2H5OH + 3O2 –> 2CO2 + 3H2O


(Alcohol burns with blue flames. This reaction releases a lot of heat.)

 Oxidation of ethanol

Two common oxidising agents are used for the oxidation of ethanol which are

- acidified potassium dichromate(VI) solution (orange to green)


- acidified potassium manganate(VII) solution (purple to colourless).

C2H5OH + 2[O] –> CH 3COOH + H2O

Ethanol oxidised to form ethanoic acid

 Dehydration

Alcohol can change to alkene by dehydration. It results in the formation of a C=C double
bond.

C2H5OH –> C2H4 + H2O

Two methods are being used to carry out a dehydration in the laboratory.

a) Ethanol vapour is passed over a heated catalyst such as aluminium oxide,


porcelain chips, or porous pot.
b) Ethanol is heated under reflux at 180°C with excess concentrated sulphuric acid,
H2SO4.
Carboxylic Acids
1. General formula: C nH2n+1 COOH. Where n = 0, 1, 2, 3 … (n = number of carbon)

2. Carboxylic acids are non-hydrocarbons which contain carbon, hydrogen and oxygen atoms.

Name of carboxylic acids Molecular formula of alcohol


Methanoic acid(Formic acid) HCOOH
Ethanoic acid(Acetic acid) CH3COOH
Propanoic acid C2H5COOH
Butanoic acid C3H7COH

3. Physical properties of carboxylic acid

Name Molecular formula Boiling point (°C)


Methanoic acid(Formic acid) HCOOH 101
Ethanoic acid(Acetic acid) CH3COOH 118
Propanoic acid C2H5COOH 141
Butanoic acid C3H7COH 164

 Solubility – generally in carboxylic acid (the less than four carbon atoms) are very
soluble in water and ionise partially to form weak acid.
 Density – density of carboxylic acid increases down the series
 Boiling points – relatively high boiling points than the corresponding alkanes.
 Colour and Smell – colourless and pungent smell

4. Preparation of carboxylic acid

 Oxidation of an alcohol
The oxidation of ethanol is used to prepare ethanoic acid.

C2H5OH + 2[O] –> CH 3COOH + H2O


Carried out by refluxing* ethanol with an oxidising agent
- acidified potassium dichromate(VI) solution – orange colour turns to green
- acidified potassium manganate(VII) solution – purple colour turns to colourless
* reflux = upright Liebig condense to prevent the loss of a volatile liquid by vaporisation.
5. Chemical properties of carboxylic acid

 Reaction with metals


Ethanoic acid reacts with reactive metals (copper and metals below it in the reactivity
series cannot react with ethanoic acid).
(K, Na, Mg, Al, Zn, Fe, Sn, Pb, Cu, Ag, Au)

2CH3COOH + Zn –> Zn(CH3COO)2 + H2

 Reaction with bases & alkali (neutralization)

CH3COOH + NaOH –> CH3COONa + H2O


In this reaction, a salt (sodium ethanoate) and water are formed.

 Reaction with carbonates


Ethanoic acid reacts with metal carbonates (calcium carbonate, magnesium carbonate)

2CH3COOH + CaCO3 –> Ca(CH3COO)2 + CO2 + H2O


In this reaction, a salt (calcium ethanoate), carbon dioxide and water are formed.

 Reaction with alcohols (Esterification)


Ethanoic acid reacts with alcohol

CH3COOH + C4 H9OH –> CH3COOC4H9 + H 2O (Concentrated H2 SO4 is the catalyst)


In this reaction, an ester (colourless sweet-smelling liquid) butyl ethanoate and water are
formed.
Esters
1. General formula: C nH2n+1 COOC mH 2m+1 . Where n = 0, 1, 2, 3 … and m = 1, 2, 3 … (n and m =
number of carbon)

2. Esters are non-hydrocarbons which contain carbon, hydrogen and oxygen atoms.

Alcohol + Carboxylic acid Molecular formula of ester Name of ester


Ethanol + Methanoic acid HCOOC2H5 Ethyl methanoate
Methanol + Ethanoic acid CH3COOCH3 Methyl ethanoate
Propanol + Ethanoic acid CH3COOC3H7 Propyl ethanoate
Ethanol + Propanoic acid C2H5COOC2H5 Ethyl propanoate

3. Physical properties of ester

 Simple esters are colourless liquid and are found in fruits and flowers.
 sweet pleasant smell.
 insoluble in water but soluble in organic solvent.
 less dense than water.
 cannot conduct electricity.
 The higher and more complex esters have higher boiling points and less volatile.

Fats
 non-hydrocarbons which contain carbon, hydrogen and oxygen atoms.
 belonging to the group in ester.
 are formed from glycerol and fatty acids.

Name of fat Types of fatty acids


Lauric acid* Saturated
Palmitic acid* Saturated
Stearic acid* Saturated
Oleic oxide ** Unsaturated
Linoleic acid*** Unsaturated
Linolenic acid*** Unsaturated

* Saturated: C-C single bonds

** Unsaturated (monounsaturated): C=C double bonds

*** Unsaturated (polyunsaturated): C=C double bonds


1. Animal fats have higher percentage of saturated fats than unsaturated fats.

2. Plant oils have higher percentage of unsaturated fats than saturated fats.

3. Physical properties of fats

Types of fats Saturated Unsaturated


Bonding C-C single bonds C=C double bonds
Melting point higher lower
Sources animals plants
State at room temperature solid liquid

Fats (animal) in general are solids at room temperature and acted as:

 protective cushion to protect the vital organ


 provide energy and stored in body
 carry Vitamin A, D, E, K (insoluble in water)

Fats (plant) are called oils. Oils are liquids at room temperature.

4. Chemical properties of fats

 Unsaturated fats can be converted into saturated fats by hydrogenation (additional


reaction) in 180°C in the presence of nickel catalyst.

5. Effect of fats

High consumption of fatty food will results:

 obesity
 high blood pressure
 arteries become hard and leading to heart problems and stroke
Natural rubber
 Monomer: isoprene, 2-methylbuta-1,3-diene.

1. Structure of rubber molecule

 Latex is colloid (35% rubber particles and 65% water).


 Rubber particle contains rubber molecules which are wrapped by a layer of negatively-
charged protein membrane. Same charge of rubber molecules repels each other. This
prevent rubber from coagulate.

2. Coagulation process of latex

The process for the coagulation of latex is summarised as:

1. Acid (H +) neutralise the negatively-charged protein membrane.


2. The rubber molecules will collide one another after the protein membrane is neutralised.
3. Rubber molecules (polymers) are set free when the protein membrane is break down
4. Rubber molecules combine with one another (coagulation).

3. Natural coagulation process of latex

1. Latex is exposed to air without adding acid


2. Coagulation process occurs in slower pace due to the bacteria action (which produce acid)

4. Prevent coagulation process of latex

1. Alkaline / Basic solution is added to the latex. Example: ammonia (NH3).

5. Properties of natural rubber

 elastic
 cannot withstand heat (become sticky and soft – above 50°C; decompose – above 200°C;
hard and brittle – cooled)
 easily oxidised (present of C=C)
 insoluble in water (due to the long hydrocarbon chains)
 soluble in organic solvent

6. Vulcanisation of rubber

Vulcanisation – process of hardening rubber and increases rubber elasticity by heating it with
sulphur or sulphur compounds.
7. Comparison of vulcanised rubber and unvulcanised rubber

Properties Vulcanised rubber Unvulcanised rubber


Double bonds Decreases (formation of sulphur cross-links) More number of double bonds
Melting point High (presence of sulphur) Low
Elasticity More elastic (sulphur cross-links prevents the Less elastic
polymer chain or rubber from slipping past)
Strength and hardness Strong and hard Weak and soft (polymer chain of rubber will
break when rubber is over stretched.
Resistant to heat Resistant to heat Poor resistant to heat
Oxidation Resistant to oxidation (less number of double Easily oxidised by oxygen (many double bonds
bonds per rubber molecule) per rubber molecules)