Organic Chemistry

Introduction
 Hydrocarbon: compound that consists of carbon and hydrogen atoms only.
 Homologous series: a ‘family’ of similar compound with similar chemical properties due to the
presence of the same functional group.
 Functional group: a specific group of atoms within a compound that is responsible for the
characteristic chemical reactions of that compound.
 Molecular formula: a formula giving the number of atoms of each of the elements present in one
molecule of a specific compound.
 Isomer: compounds that have the same molecular formula but different structure.
Molecular formula Condensed formula Displayed structural formula Skeletal formula

C3H6 CH2=CHCH3

Number Stem Alkane Alkene Alcohol Carboxylic Acid

of carbon
1 Meth- Methane - Methanol Methanoic acid
2 Eth- Ethane Ethene Ethanol Ethanoic acid
3 Prop- Propane Propene Propanol Propanoic acid
4 But- Butane Butene Butanol Butanoic acid
5 Pent- Pentane Pentene Pentanol Pentanoic acid
6 Hex- Hexane Hexene Hexanol Hexanoic acid
7 Hept- Heptane Heptene Heptanol Heptanoic acid
8 Oct- Octane Octene Octanol Octanoic acid
9 Non- Nonane Nonene Nonanol Nonanoic acid
10 Dec- Decane Decene Decanol Decanoic acid

Homologous series Functional group General formula Example

Alkane Only C-C CnH2n+2

Alkene C=C CnH2n

Alcohol -OH CnH2n+1OH

Carboxylic acid -COOH CnH2n+1COOH

Ester -COOC- CnH2n+1COOCmH2m+1

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General Properties of Organic Compounds
 Organic compounds are generally insoluble in water except alcohols and carboxylic acids.
 Melting and boiling points and viscosity increase as the number of carbon increases in a homologous
series. This is because there is an increase in the mass of the compound as it moves up the series.
 Organic compounds can undergo combustion to produce water, carbon dioxide, and energy in excess
of oxygen.
 When oxygen is insufficient, organic compounds undergo incomplete combustion to form carbon
monoxide, water, and energy OR carbon, water, and energy instead.

Naming an Organic Compound

Prefix (substituents) + Stem (number of carbon) + Suffix (functional group)
1. Determine the longest carbon chain (stem).
2. Determine the functional group (suffix).
3. Determine the carbon 1.
 Check both terminal carbon.
 Carbon 1 is the terminal carbon that gives the lowest carbon number for the nearest
functional group or side-chain substituent.
4. Add the location (carbon number) of the functional group.
5. Determine the locations of the side-chain substituents.
6. Order the prefixes in alphabetical order.
7. Add di/tri/tetra, if required, to indicate the number of a particular substituent.
8. Add the locations (carbon numbers) of the side-chain substituents.
9. Use a hyphen to link a number and a letter, e.g., 2,3-dimethylbutane.

Fuel
 Petroleum: a mixture of hydrocarbons and its separation into useful fractions by fractional distillation
 Distillation of petroleum:
o Petroleum is heated up to 350°C-450°C.
o The vapour is then condensed in fractionating column.
o The fractions will be distilled according to its boiling points.
o The fraction with lowest boiling point will be collected at the top of the fractionating column.
 The table below shows the uses of the fractions of petroleum. The fractions have been arranged in
order of distillation from the top.
Fraction Carbon atoms Uses
Refinery gas C1 – C4 Bottled gas for heating and cooking
Gasoline/ petrol C4 – C12 Fuel / petrol in cars
Naphtha C7 – C14 Making chemicals
Kerosene / paraffin C12 – C16 Jet fuel
Diesel oil / gas oil C14 – C18 Fuel in diesel engine
Fuel oil C19 – C25 Fuel for ships and home heating systems
Lubricating oil C20 – C40 Lubricants, waxes and polishes
Bitumen > C70 Making roads

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Alkane
 It has general formula of CnH2n+2.
 Alkane is generally unreactive organic compound (except during combustion)
 Alkane is a saturated hydrocarbon because it does not have C=C nor C≡C so it cannot accept any
extra atoms anymore.

Reaction
(Free Radical) Substitution Reaction with Chlorine Gas
o In the presence of UV light, a hydrogen atom in alkane can be substituted by a chlorine atom
from chlorine gas. In excess of Cl2, all hydrogen atoms can be substituted by chlorine atoms.
𝑙𝑖𝑔ℎ𝑡
o E.g., CH4 + Cl2 → CH3Cl + HCl

Combustion
o Alkane burns completely in excess of oxygen gas to form carbon dioxide and water.
o E.g., CH4 + 2O2 → CO2 + 2H2O
o Incomplete combustion can happen if there is not enough oxygen gas. Carbon monoxide or
carbon and water will be formed instead.
o E.g., 2CH4 + 3O2 → 2CO + 4H2O or CH4 + O2 → C + 2H2O

Cracking
o Breaking long-chain / large hydrocarbons into short-chain / small hydrocarbons.
o Long-chain alkane is cracked to give shorter-chain alkane and short-chain alkene OR alkenes
and hydrogen gas.
o Condition: 500°C; Al2O3 or SiO2 as catalyst.
𝐴𝑙2 𝑂3 ,500°𝐶
o E.g., C10H22 → C8H18 + C2H4

Alkene
 It has general formula of CnH2n.
 Alkene is more reactive than alkane as it can undergo addition reaction.
 Alkene is an unsaturated organic compound because it has C=C that can be broken to accept extra
atoms.

Preparation of Alkene
Cracking
 Breaking long-chain / large hydrocarbons into short-chain / small hydrocarbons.
 Long-chain alkane is cracked to give short-chain alkenes and short-chain alkanes OR hydrogen gas.
 Condition: 500°C; Al2O3 or SiO2 as catalyst.
𝐴𝑙2 𝑂3 ,500°𝐶
 E.g., C10H22 → C8H18 + C2H4

Dehydration of Alcohol
 Water is removed from alcohol to form alkene in the presence of a strong acid (e.g., concentrated
H2SO4) or Al2O3, broken pot at high temperature.
𝐴𝑙2 𝑂3 𝑜𝑟 𝑐𝑜𝑛𝑐. 𝐻2 𝑆𝑂4
 E.g., CH3CH2OH→ CH2=CH2 + H2O

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Reaction
Combustion
 Like other hydrocarbons, alkene can also undergo combustion. It burns completely to form carbon
dioxide and water in excess of oxygen. In incomplete combustion, alkene forms water and carbon
monoxide OR carbon.

Addition reaction
 C=C is broken during addition reaction to allow other substituents to be attached to it.
 Bromination (test for unsaturated carbon)
o When liquid bromine is added to an alkene, the brown solution will turn colourless.
o E.g., CH2=CH2 + Br2 CH2BrCH2Br
 Hydrogenation (alkene to alkane)
o Condition: hydrogen gas; 200°C; nickel or platinum as catalyst
𝑁𝑖 𝑜𝑟 𝑃𝑡;200°𝐶
o E.g., CH2=CH2 + H2→ CH3CH3
 Hydration (alkene to alcohol)
o Condition: steam; 300°C; 60 atm; H3PO4 as catalyst
o E.g., CH2=CH2 + H2O  CH3CH2OH
 Addition polymerisation
o Condition: high pressure, high temperature, catalyst

o E.g.,

Alcohol
 It has general formula of CnH2n+1OH.
 Small-chain carbon alcohol (e.g., ethanol) is soluble in water.
 Ethanol is used as solvent, especially to dissolve organic compound.
 Ethanol is used as solvent in glue, printing ink and perfumes because it evaporates easily (b.p. 78°C).
 Ethanol is a renewable fuel (obtained from fermentation of sugar) and burns cleanly.

Preparation of Ethanol
Fermentation Hydration of Ethene
 Result of anaerobic respiration of yeast  Result of addition reaction of ethene and
(single-cell fungi) at 30°C steam at 300°C and 60 atm with H3PO4 as
 Glucose  ethanol + carbon dioxide catalyst
 C6H12O6 →
𝑦𝑒𝑎𝑠𝑡
2 C2H5OH + 2 CO2  CH2=CH2 + H2O  CH3CH2OH
Advantages: Advantages:
 Renewable raw material  Fast rate of reaction
 Require little energy  Not labour intensive
 Good use of waste organic material  Continuous process
 Relatively inexpensive  Pure product
Disadvantages: Disadvantages:
 Labour intensive (plantation workers)  Non-renewable raw material
 Impure products, require further  Expensive because high temperature and
treatment pressure condition needed
 Slow rate of reaction  Require a lot of energy

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Reaction
Combustion
 Like other organic compound, alcohol can also undergo combustion. It burns completely to form
carbon dioxide and water in excess of oxygen. In incomplete combustion, alcohol forms water and
carbon monoxide OR carbon.

Oxidation (Alcohol to Carboxylic Acid)

 Alcohol can be oxidised to carboxylic acid using acidified potassium manganate (VII), KMnO4 or hot
potassium dichromate (VI), K2Cr2O7.
 When KMnO4 is used, the colour changes from purple to colourless. When K2Cr2O7 is used, the colour
changes from orange to green.
 E.g., CH3CH2OH + 2[O]  CH3COOH + H2O

Esterification
 Alcohol can react with carboxylic acid to form sweet-smelling ester.
 Reflux is required to ensure that all volatile reactants are used up.
 Condition: concentrated sulfuric acid as catalyst, reflux.
 E.g., CH3CH2COOH + CH3CH2OH  CH3CH2COOCH2CH3

Dehydration
 Water is removed from alcohol to form alkene in the presence of a strong acid (e.g., concentrated
H2SO4) or Al2O3 at high temperature.
𝐴𝑙2 𝑂3 𝑜𝑟 𝑐𝑜𝑛𝑐. 𝐻2 𝑆𝑂4
 E.g., CH3CH2OH→ CH2=CH2 + H2O

Carboxylic Acid
 It has general formula of CnH2n+1COOH
 Carboxylic acid is a weak acid as it only dissociates partially.
 It has similar reaction as mineral acids.
 Ethanoic acid / acetic acid / vinegar is the most common carboxylic acid.
 Ethanoic acid has strong sour smell.

Preparation of Carboxylic Acid

 Carboxylic acid is prepared by oxidising alcohol using acidified potassium manganate (VII), KMnO4 or
hot potassium dichromate (VI), K2Cr2O7.
 When KMnO4 is used, the colour changes from purple to colourless. When K2Cr2O7 is used, the colour
changes from orange to green.
 E.g., CH3CH2OH + 2[O]  CH3COOH + H2O

Reaction
Esterification
 Carboxylic acid can react with alcohol to form sweet-smelling ester.
 Reflux is required to ensure that all volatile reactants are used up.
 Condition: concentrated sulfuric acid as catalyst, reflux.
 E.g., CH3CH2COOH + CH3CH2OH  CH3CH2COOCH2CH3

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Acid-Base Reaction
 Acid + base / alkali  salt + water
o E.g., CH3COOH + NaOH  CH3COONa + H2O
 Acid + metal carbonate  salt + water + carbon dioxide
o E.g., 2 CH3COOH + CaCO3  (CH3COO)2Ca + H2O + CO2
 Acid + metal  salt + hydrogen gas
o E.g., 2CH3COOH + 2Na  2CH3COONa + H2

Ester
 It has a general formula of CnH2n+1COOCmH2m+1
 Ester is a sweet-smelling compounds, used in perfume and food flavouring.
 Ester is not soluble in water but it is soluble in ethanol.

Preparation of Ester
 Ester is prepared through esterification reaction between carboxylic acid and alcohol.
 Reflux is required to ensure that all volatile reactants are used up.
 Condition: concentrated sulfuric acid as catalyst, reflux
 E.g., CH3CH2COOH + CH3CH2OH  CH3CH2COOCH2CH3

Naming of Ester
 The component with C=O will become the stem with –oate 2 carbons, contains C-O
ethyl
suffix, while the component with C-O will become the prefix
O
with with –yl suffix. H H
H
 In short, the carboxylic acid will become the stem with –oate C
H
C C H

suffix while the alcohol will become the prefix (substituent) H C O C

H
H
H H
with –yl suffix.
 E.g., ethanol + propanoic acid  ethyl propanoate + water 3 carbons, contains C=O
propanoate

Reaction
Hydrolysis
 A reaction in which bond is broken by water.
 Ester can undergo hydrolysis in the presence of acid or alkali.
 Acid hydrolysis
o Acid hydrolysis is a reversible reaction
𝑎𝑐𝑖𝑑
o Ester + water ↔ carboxylic acid + alcohol
𝑎𝑐𝑖𝑑
o Ethyl propanoate + water ↔ propanoic acid + ethanol
𝑎𝑐𝑖𝑑
CH3CH2COOCH2CH3 + H2O ↔ CH3CH2COOH + CH3CH2OH
 Alkaline hydrolysis (saponification)
o Alkaline hydrolysis is an irreversible reaction
o Ester + alkali  carboxylate salt + alcohol
o Ethyl propanoate + sodium hydroxide  sodium propanoate + ethanol
CH3CH2COOCH2CH3 + NaOH  CH3CH2COONa + CH3CH2OH

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Fats / Lipids
 Fats or lipids are esters, made of glycerol and three fatty acids.
 Like esters, fats have ester linkages and can undergo hydrolysis.
𝑎𝑐𝑖𝑑
 Acid hydrolysis: fats + water ↔ fatty acid + glycerol
 Alkaline hydrolysis: fats+ alkali  carboxylate salt + glycerol

Polymers
 Polymers: large molecules built up from small units (monomers).
 Monomers: a molecule that is able to bond in long chains.
 Repeat unit: a part of a polymer whose repetition would produce the complete polymer chain
Polymers Monomers Link Example

Polyalkene Alkene + alkene C-C

Polyester Dicarboxyclic acid + diol -COOC-

Polyamide /
Dicarboxylic acid + diamine / amino acid + amino acid -CONH-
polypeptide

Polymerisation
Addition polymerisation Condensation polymerisation
 Addition reaction  Condensation reaction
Reaction  Monomers join together by opening  Small molecule (usually water) is
the C=C double bonds removed
 Single type of monomer  At least 2 types of monomers
Monomer  Unsaturated monomer, usually  Reactive functional groups at ends of
contains C=C molecules (e.g., -COOH, -OH, -NH2)
 Single product, no by-product  Two products; polymer and small
Nature of  Non-biodegradable molecule (usually water)
product  Resistant to acids  Biodegradable
 Hydrolysed by water

Synthetic polymers

Natural polymers
 Some of natural polymers exist as food constituents.
 The main constituents of food are proteins and carbohydrates.

Proteins
 Proteins are made of amino acid (monomers) joined together by condensation polymerisation.
 Proteins possess the same amide (peptide) linkage as nylon but with different units / arrangement.

 In proteins, the amide / peptide linkages (–CONH–) are repeated in the same way while in nylon, the
linkages are alternating between –CONH– and –NHCO–.
 Proteins can undergo hydrolysis to form amino acids.

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 o Protein + water  amino acids

Carbohydrates
 Carbohydrates are made of large numbers of sugar units ( ) joined together by
condensation polymerisation.
 Carbohydrates possess glycosidic bonds / ether linkages (C-O-C) o join the sugar units (monomers).

 Carbohydrates can undergo hydrolysis, breaking the glycosidic bonds, in the presence of acid or
enzyme to form simple sugar.
𝑎𝑐𝑖𝑑 / 𝑒𝑛𝑧𝑦𝑚𝑒
o Carbohydrate + water → simple sugar

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Summary

Production Reaction

Alkane

Alkene

Alcohol

Carboxylic
acid

Ester

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