ORGANIC CHEMISTRY

What is organic chemistry?

The study of the structure, properties, and reactions of organic compounds and organic
materials, i.e., matter in its various forms that contain carbon atoms.
All living things are made from organic compounds based on chains of carbon atoms which
are not only covalently bonded to each other but also covalently bonded to hydrogen, oxygen
and/or other elements.

Fractional distillation of Crude Oil (Petroleum)

Fractional distillation of Crude Oil (Petroleum) Steps
1. The crude oil is heated to 400 degrees, vaporizing all parts.
2. Each fraction will contain hydrocarbons within a certain range of boiling points. Eg
petrol contains hydrocarbons between 30 and 110 degrees (between 5 and 10 carbons
long).
3. The liquids condensing at different levels are collected on trays.
4. These liquids may need further refining by more distillation.

Big hydrocarbons = high boiling points →condense in the lower part of the tower.
Small hydrocarbons = low boiling points →condense in higher parts of the tower

Fractional distillation of Crude Oil (Petroleum) Properties

Hydrocarbons: compounds having hydrogen and carbon only.
Homologous series: a group of compounds which have the same general formula,
functional group, similar chemical properties but a trend in physical properties.
Isomerism: isomers are compounds having same molecular formula but different structural
formula. All the three compounds shown above are isomers of each other. They have the
same molecular formula C4H8, but they have different structures.

Organic Families

Alkanes

Alkenes

Alcohols

Carboxylic Acids
Basic Names
ALKANES
General formula is CnH2n+2 (n=1,2,3….)
They are saturated hydrocarbons: containing carbon-carbon single bonds.
The first 5 alkanes are gases at room temperature and pressure.

NAMING ALKANES DRAWING ALKANES

1- Select the longest chain of C atoms.
2- place the ending -ANE on the basic
name
1- Draw all the C atoms in a straight chain
linked with single bonds.
2- Surrounding each C atom, add as
many single bonds to ensure each C
atom has FOUR bonds.
3- Add H atoms

Physical properties: as the molecules get larger (carbon number increases)

1. Molecular mass increases.
2. Melting and boiling point increases.
3. Viscosity increases.
4. Flammability decreases.

Chemical properties: alkanes are generally unreactive as they are saturated

compounds.
1. Combustion: alkanes undergo complete and incomplete combustion producing
either CO2, CO or C and water (H2O) as products.

Example:
Complete combustion
CH4(g) + 2O2(g) CO2(g) + 2H2O(g)
Incomplete combustion
2CH4(g) + 3O2(g) 2CO(g) + 4H2O(g)
CH4(g) + 2O2(g) C (s) + 2H2O(g)
 2. Substitution reactions: alkanes undergo substitution reaction with halogens
like, Br2,Cl2, and F2 in the presence of UV light or sunlight.
Example: 1) methane reacts with chlorine in the presence of UV light and form
four products.
CH4(g) + Cl2(g) CH3Cl(g) + HCl(g)
A chain reaction takes place and other products are CH2Cl2, CHCl3 and CCl4
2) ethane reacts with fluorine in the presence of UV light and form six products.
C2H6(g) + F2(g) C2H5F(g) + HF(g)
A chain reaction takes place and other products are C2H4F2 C2H3F 3 and C2H2F 4,
C2HF5 and C2F6.
The reaction with fluorine is faster than chlorine due to its reactivity increases
down the group.

CRACKING
1. To break up large hydrocarbon molecules into smaller ones to produce fuel for motor
vehicles.
2. It is also a means of producing alkenes.
3. Cracking is also a chemical reaction of producing hydrogen gas.
Conditions for cracking
Cracking is done by passing the hydrocarbon vapour over catalyst
Al2O3 or SiO2 at a temperature 5000C

Example:
C2H4 + C6H14

C8H18 2C3H6 + C2H6

2C2H4 + C4H8 + H2
ALKENE
General formula: CnH2n (n=2,3,4…)
Alkenes are unsaturated hydrocarbons. Contains at least one carbon= carbon
double bonds.
NAMING ALKENES
1- Select the longest chain of C atoms
containing the double bond.
2- Place the ending -ENE on the basic name.
3- use a number to indicate the lower number
carbon of the C=C.
DRAWING ALKANES
1- Draw all the C atoms in a straight chain
linked with one double bond and the rest
as single bonds
2- Surrounding each C atom, add as many
single bonds to ensure each C atom has
FOUR bonds.
3- Add H atoms
 Physical properties are similar to that of alkanes.

Chemical reactions: alkenes are more reactive than alkanes , due to the presence of
double bonds
1. Combustion reactions similar to alkanes
Complete combustion
C2H4(g) + 3O2(g) 2CO2(g) + 2H2O(g)
Incomplete combustion
2C2H4(g) + 4O2(g) 4CO(g) + 4H2O(g)
C2H4(g) + 2O2(g) 2C (s) + 2H2O(g)
2. Addition reactions:
Alkenes undergo addition reactions, due to the presence of double bonds,
Hydrogenation: addition of hydrogen to form an alkane in the presence of nickel
catalyst and temperature 1500C to 3000C (conditions).
- C2H4(g) + H2(g) C2H6 (g)
- vegetable oil + H2 margarine
Halogenation: addition of bromine to form a halo alkane
C2H4(g) + Br2(g) C2H4Br2 (g)
Test for unsaturation: adding bromine water to alkane will not decolourise(orange
colour remain same) where as with alkene the bromine water will decolourise from
orange to colourless.
Hydration :catalytic addition of steam to alkene will produce alcohol
Conditions: 3000c temperature, 60 atm and phosphoric acid catalyst

- C2H4(g) + H2O(g) C2H5OH (l)

Polymerization: Alkene undergo addition polymerization due to the presence of double
bonds.
Polyunsaturated: presence of many double bonds between
carbon -carbon atom

ALCOHOL
General formula : CnH2n+1OH ( n = 1,2,3….)
Alcohol contains the hydroxyl group –OH as a functional group.
 Physical properties few members (C1 –C4) are liquids and soluble in water.
solubility decreases as the carbon atom increases.

NAMING ALCOHOL DRAWING ALCOHOL

1- Select the longest chain of C atoms
containing the –OH group.
2- Place the ending -OL on the basic name.
1- Draw all the C atoms in a straight chain
linked with single bonds.
2- Surrounding each C atom, add as many
single bonds to ensure each C atom has
FOUR bonds.
3- Add one OH group.
4- Add H atoms to the remaining bonds

Chemical reactions :
1. Dehydration of alcohol produces alkenes. Conditions are concentrated sulfuric
acid at 1700C

C2H5OH (l) C2H4(g) + H2O(g)

2. Oxidation : alcohol on oxidation produces alkanoic acid or carboxylic acid. using
oxidisng agent like acidified potassium permanganate or acidified potassium
dichromate
Eg: C2H5OH (l) + 2[O] CH3COOH + H2O
H+/KMnO4 (colour changes from purple to colourless)

-C3H7OH (l) + 2[O] C2H5COOH + H2O

3. Reaction with metals: alcohols on reacting with metals it form alkoxide
2C2H5OH (l) + 2Na 2C2H5ONa + H2
sodium ethoxide
 Manufacture of ethanol
Fermentation of sugar Catalytic addition of steam to
ethene
C6H12O6 2C2H5OH + 2CO2 -C2H4(g) + H2O(g) C2H5OH
Conditions: yeast as a catalyst Conditions: 3000c temperature,
and a optimum temperature 370C - 60 atm and phosphoric acid
420C, catalyst
-slow process -fast process
- 14% concentration. - 100% concentration..
- get poisoned keeping for a long - obtain from a non renewable
period of time. resources
- obtain from a renewable
resources

Uses of ethanol:
1. As a solvent for medicines, perfumes, detergents, dyes and varnishes.
2. As a fuel, either by itself or mixed with petrol in cars.
3. As a constituent in alcoholic drinks.
4. To make esters, perfumes, food essences

CARBOXYLIC ACID

Properties
General formula : CnH2n+1 COOH ( n = 0,1,2,3….)
Carboxylic acid contains the carboxyl group –COOH as a functional group.
Physical properties few solids are soluble in water. solubility decreases as the carbon
atom increases.
Weak acids ionizes partially when dissolved in water

Eg:1. CH3COOH(aq) CH3COO- (aq) + H+ (aq)

Ethanoate ion
 Eg.2.

Chemical reactions :
1, Carboxylic acids reacts with metals, metal oxides, metal hydroxides, metal
carbonates and metal hydrogen carbonates to form salts
2CH3COOH(aq) + 2Na(s) 2CH3COONa(aq) + H2(g)
Sodium ethanoate
2CH3COOH(aq) + MgO(s) (CH3COO)2Mg(aq) + H2O(l)
magnesium ethanoate
2CH3COOH(aq) + Ca(OH)2(aq) (CH3COO)2Ca(aq) + 2H2O(l)
calcium ethanoate
2C2H5COOH(aq) + Na2CO3(s) 2C2H5COONa(aq) + H2O(l)
Sodium propanoate

2. ESTERIFIATION: Esters are sweet smelling liquid acid which are formed when a
reaction took place between an alcohol and carboxylic acid .
Conditions: concentrated sulfuric acid H2SO4 and heat
CH3COOH(aq) + C2H5OH CH3COOC2H5(aq) + H2O(l)
Ethanoic aicd ethanol ethyl ethanoate

Uses of esters:
1) Esters are used as solvent in the manufacture of liquors and in nail polish.
2) They are used to make food essences and perfumes.
 POLYMERISATION
Addition polymerization
Unsaturated compounds only undergo addition polymerization.
The double bonds in monomers break and they joined together to form a long chain.

Monomer Polymer Uses

Name Formula Name Formula
Ethene Polyethene Plastic bags,
(Polythene) sheets, bowls,
film, etc.
Propene Polypropene Crates, plastic
ropes,bottles,c
ontainers,etc

Chloroeth Polychloroeth Water proof

ene ene and insulating
(vinyl (PVC or material, pipes
chloride) polyvinylchlo and guttering
ride) ,records
Phenyl Polyphenyleth Insulation
ethene ene Packaging,
(styrene) (polystyrene) (foam)celing
tiles
Tetra Polytetrafluor Non-stick
fluoroethe oethene(PTFE sauce-
ne or Teflon) pans,bridge
bearings
Acrylonitr polyacrylonitr Synthetic fibre
ile ile for
carpet,clothes,
etc.
methymet Polymethyme Glass subsitute
hacrylate thacrylate
(Perspex)
 Condensation polymerization
Condensation polymerization is a process where two monomers react together to
produce a large molecule, with the elimination of a small molecule like water,
(H2O), ammonia. (NH3), hydrogen chloride. HCl
Example:
1) Nylon: Amide linkage–CONH- is found in nylon
Monomers used: Dicarboxylic acid and Diamine
HOOC— —COOH + NH2— —NH2

- H2O

(polyamide)
Properties and uses of nylon
Nylon is strong yet light. It can be stretched without breaking.
It is woven into cloth to manufacture raincoats, parachutes and tents.
Nylon is made into fibers to produce strong ropes, fishing lines and carpets.
It is used to make curtain rail fittings cupboard hinges and gear wheels.

2) Protein: Amide linkage(-CONH-) is found in protein (natural polymer)

Monomers used: amino acids

- H2O

(p
polyamide/polypeptide)
 Hydrolysis of Proteins

Proteins can be broken down into their constituent amino acids by hydrolysis (addition of
water).
Hydrolysis is carried out by heating the protein with a dilute acid or alkali or even
enzymes.
Protein + water HCl amino acids
+
TERYLENE: a ester( linkage is -COO-) is found in terylene

Monomers used: Dicarboxylic acid and Diol

HOOC— —COOH + HO — —OH

-H2O

Properties and uses of Terylene

Terylene is made into fibres which are woven into cloth. This polymer lasts longer
than cotton. It is easier to wash and dry. Therefore polyester is used widely to
produce clothes such as “T” shirts.

Terylene can also be used to produce films which are then used for making
recording tapes.

Fat: Ester linkage(-COO-) is found in fats

Monomers used: fatty acids and glycerol

Hydrolysis of fats
Fats can be hydrolysed with an acid or alkali.
 Alkaline hydrolysis of fats is also called saponification. When fats are boiled with an
alkali like sodium hydroxide.

+ 3NaOH +

Monomers used: diol

-H2O
n( C6H12O6)
(C6H12O6)n +
nH2O
Glucose units
Starch chain

Hydrolysis of carbohydrates
-Carbohydrates can be broken down into simple sugars such as glucose by hydrolysis
with warm acids or alkalis.

Advantages of plastics
They can be easily shaped in single step by mould.
Plastics are much more resistant to chemical environments than most metal, wood or
paper products.
Light weight and not corrode.

Disadvantages of plastics
They are made from petrochemicals, which are finite source.

Pollution caused by plastics.

Plastics are non bio degradable and cannot be decomposed by bacteria in the
environment.
Plastic objects accumulate and pollute the environment.
They are carbon based polymers which burn to produce sooty flame and release
toxic fumes like carbon monoxide and hydrogen chloride, HCl from PVC causing air
pollution.