Organic Chemistry

Organic Compound

Contain carbon and

hydrogen, and often other
elements such as oxygen,
nitrogen and halogen
（chlorine, bromine)

Carbon atoms can join

together to form chains,
branched chains and rings.
 Hydrocarbon
• Hydrocarbon contains carbon and hydrogen only.
• The carbon atoms are joined together with single, double or triple
bonds, C-C, C=C, C三C
• Carbon atoms are joined to hydrogen atoms by single bonds. C-H
• C forms four bonds and H form one bond
Bond number of different element
• C： 4 bonds H2C=CH2
• H: 1 bond
• O: 2 bonds H3C-O-H
• CI/Br: 1 bond C-Br H3CBr
• N: 3 bonds H3CNH2
Saturated or unsaturated hydrocarbon
Saturated hydrocarbon: only contains single C-C bonds

Unsaturated hydrocarbon: contains double or triple bond, C=C, C三C

 empirical formula, molecular formula and structural formula
• A molecular formula consists of the chemical symbols for the constituent elements followed by numeric
subscripts describing the number of atoms of each element present in the molecule.
• Empirical formula represents the simplest whole integer ratio of atoms in a compound
• Molecular formula for a compound can be the same as or a multiple of the compound’s empirical formula.
• Structural formula is used to indicate not only the number of atoms, but also their arrangement in space

Empirical formula Molecular formula Structural formula: C6H14

Molecular formula: C9H21

empirical formula: C3H7 Molecular formula: C6H14

Molecular formula: C12H28

Atom number Show all elements with

number of all atoms Show structure in detail
simplified formula
Structural formula: displayed formula-condensed formula

• Displayed formula: full structural formula to show all bonds in

molecule as individual line. Each line represents a covalent bond

=: double bond, two pairs of shared electrons

CH3CH2CH2CH3 CH3CH=CHCH2CH3

• Condensed structural formula: Omitting all the C-C and C-H

single bond CH3CH2CH3
Same molecule has same structure? C4H10

Same
C-C-C-C, straight line
 Functional group
• Functional group is an atom or a group of atoms that determine the chemical properties of a compound
• All compounds in the same homologous series have the same functional group.
Alkanes and Alkenes
Alkanes:
• a homologous series of similar hydrocarbons, all the carbons are joined to
each other with single covalent bonds
• Name ending: -ane
• Formula: CnH2n+2
Side chain as functional group, -yl

CH3- methyl

CH3CH2- ethyl

CH3CH2CH2- propyl
CH3CH2CH2CH2- butyl
Alkanes and Alkenes
Alkenes:
• a homologous series of similar hydrocarbons contains carbon-carbon double
bonds
• Name ending: -ene
• Formula: CnH2n
• Positioning the double bonds for long chain, minimize the positioning number
Special structure: CnH2n but not alkenes

CH2 One cycle = one carbon-carbon double bond

C3H6 Not C3H8

H2 C CH2

CH2

C4H8 Not C4H10

H2 C CH-CH3
Alcohols
Alcohols: A homologous series of compounds contains an –OH functional group
attached to a hydrocarbon chain
• Name ending: -ol
• Formula: CnH2n+2O or CnH2nO
• Positioning -OH for long chain, minimize the positioning number
How to name:
• Find the main functional group: alkanes, alkenes, alcohols……
• Find the main carbon chain: the longest one, as base name
• Position all the functional group(attached to main chain), smaller numbers in the name

Code letters Alkanes alkenes alcohols

meth methane methanol
eth ethane ethene ethanol
prop propane Propene Propanol*
but butane Butene* Butanol*
pent pentane Pentene* Pentanol*
hex hexane Hexene* Hexanol*

* : Need to position the functional group, different position means different compound
How to name?
• Find the main functional group: alkanes, alkenes, alcohols……
• Find the main carbon chain: the longest one, as base name
• Position all the functional group （attached to main chain）, smaller numbers
in the name

• Find the main functional group: alkanes • Find the main functional group: alkanes
• Find the main carbon chain: butane • Find the main carbon chain: propane
• Position the functional group: 2-methyl • Position the functional group: 2,2-dimethyl
• Name: 2-methylbutane • Name: 2,2-dimethylpropane
How to name?
• Find the main functional group: alkanes, alkenes, alcohols……
• Find the main carbon chain: the longest one, as base name
• Position all the functional group, smaller numbers in the name

• Find the main functional group: alkenes • Find the main functional group: alkenes
• Find the main carbon chain: butene • Find the main carbon chain: butene
• Position the functional group: 1-ene • Position functional group: 2,3-dimethyl, 2-ene
• Name: but-1-ene • Name: 2,3-dimethylbut-2-ene

Note: position functional group as 1, mostly just remove 1-, but-1-ene= butene
How to name?
• Find the main functional group: alkanes, alkenes, alcohols……
• Find the main carbon chain: the longest one, as base name
• Position all the functional group, smaller numbers in the name

• Find the main functional group: alcohols • Find the main functional group: alcohols
• Find the main carbon chain: propane • Find the main carbon chain: propane
• Position the functional group: 1-ol • Position functional group: 2-ol
• Name: propan-1-ol (propanol) • Name: propan-2-ol
Decode name: How to draw a structural formula from its name?
• identify the main carbon chain as main structure
• identify the category from ending: alkanes, alkenes, alcohols……
• Identify all the functional group follow the positioning number
• Show all hydrogen to make sure C-4 bonds, H-1 bond, O-2 bonds
2,3-dimethylbut-2-ene 2-dimethylpropan-2-ol

• Identify the main carbon chain: but • Identify the main carbon chain: propan
• Identify the main functional group: alkenes • Identify the main functional group: alcohols
• Identify all functional group: : 2,3-dimethyl, 2-ene • Identify all functional group: : 2-methyl, 2-ol
• Show all hydrogen • Show all hydrogen
C–C – C -C C– C – C
CH3CCH3=CCH3 CH3
CH3
C–C =
- C-C
C–C - C CH3 – C - CH3
CH3 CH3
OH OH
 Isomerism vs isotope?
Structural isomerism
Structural isomerism: molecules with the same molecular formula, but different
structural formula

C3H8O C3H8O
C5H12

You cannot identify a clear structure only with a molecular formula, but you can use a structural formula
How to find structural isomerism?
1. Draw carbon structure without hydrogen
2. Stretch the structure to a straight chain
3. Show all functional groups
 How to identify structural isomerism?
1. Draw carbon structure without hydrogen
2. Stretch the structure to a straight chain Alkanes
3. Show all functional groups

Same ?

Draw carbon structure

Stretch the structure to a straight chain

Same
 How to identify structural isomerism?
1. Draw carbon structure without hydrogen
2. Stretch the structure to a straight chain Alkenes
3. Show all functional groups

C4H8

Draw carbon structure and stretch C

C=C-C-C C-C=C-C C=C-C

C C-C
C

Notice: you can vary the position of double bond and branch the chain to get isomerism
 Optical isomer
• Optical isomers have same structural formula, but are arranged differently in 3D
space
• Optical isomers are mirror images of each other but cannot be superimposed
• Optical isomers occurs when a molecule has a chiral centre
• Chiral centre: the carbon connected with four different atom or groups of atoms
• Chiral centre mostly occurs at double bond or cycle chains (cannot rotate)

CH3 CH3
CH3-CH = C C=CH-CH3
H

Connected with four

different atoms H
Chemical reaction of organic compounds
Combustion: another way of saying burning and involves a reaction with oxygen
Combustion of hydrocarbons in excess oxygen will produce carbon dioxide and water,
together with the release of a large amount of heat energy
Combustion of hydrocarbons in insufficient oxygen will produce, carbon monoxide or
carbon(soot) and water, together with the release of a large amount of heat energy, called
incomplete combustion, less energy than complete combustion

complete combustion incomplete combustion

Whatever the combustion produce, just balance the equation: H→ C→ O, if the number of O is
not a whole number, then make it as whole by multiple X for all numbers
Carbon monoxide is dangerous and poisonous because it reduces the
ability of the blood to carry oxygen around the body,

it has stronger combination with haemoglobin than oxygen(~200 times),

preventing it from carrying the oxygen
 Exercise on combustion
• Work out the formula of hydrocarbon that produces 4CO2+5H2O

C4H10 + 6.5 O2 → 4CO2+5H2O

2C4H10 + 13O2 → 8CO2+10H2O

• Write the balanced equation for the complete combustion of C3H8
C3H8 + 4O2 → 3CO2+4H2O

• Write the balanced equation for the complete and incomplete combustion of C8H18
2C8H18 + 25O2 → 16CO2+18H2O
2C8H18 + 17O2 → 16CO+18H2O Or 2C8H18+9O2→16C+18H2O

balance the equation: H→ C→ O

 Chemical reaction of organic compounds
Substitution reaction: an atom or group of atoms is replaced by a different atom or group of
atoms.

H is replaced by halogen Gas + Heating

Addition reaction: something is added to a molecule without taking anything away.

Alkenes undergo addition reaction

* Bromine solution is used to test for alkene. The orange solution turns colorless because addition
reaction happen between bromine and alkenes. When an alkanes is added to the bromine solution, it
remains orange because an alkane does not reaction with bromine solution
How the physical properties of hydrocarbons change with molecular
size—carbon number increase?
As the number of carbon atoms in hydrocarbon molecules increases, the
physical properties of the compound changes

• Most of these changes are the results of increasing intermolecular forces of attraction.
• As the molecules become bigger, the intermolecular attractive force become stronger→
more difficult to pull one molecule away from its neighbors
• Boiling point increase: the larger the molecule, the higher the boiling point
• The liquids become less volatile: the bigger the hydrocarbon, the more slowly it
evaporates at room temperature
• The liquids become more viscous as the molecules become bigger
• The liquids become darker in color. The stronger intermolecular attractive force make
the atoms arrangement more closely
• Bigger hydrocarbons do not burn as easily as smaller ones, which limits the use of
bigger ones as fuel, e.g. bitumen
Physical properties of fractions from crude oil
The uses of the fractions
Fractions Usage in daily life

Mixture of methane, ethane, propane and butane, commonly used as liquefied

Refinery gases
petroleum gas (LPG) for domestic heating and cooking

Gasoline (petrol) A mixture of hydrocarbons with similar boiling points, used as a fuel in cars

Used as a fuel for jet aircraft, as domestic heating oil and paraffin for small
kerosene
heater and lamps

diesel Used as fuel for buses, lorries and railway engines

Fuel oil Used as fuel for ships and for industrial heating

bitumen Melted and mixed with small pieces of rock to make the top surface of roads

Combustion enthalpy increases with Carbon number increasing but burn slowly.
The principle to separate the crude oil ?

• Crude oil is a mixture of hydrocarbon with different boiling points

• The larger the molecules, the higher boiling points.
• The boiling point is the same as the temperature at which a gas condenses to
form a liquid, called the condensation point
• Can use fractional distillation to separate into fractions which are mixtures
with similar boiling points (means a narrow range of sizes of hydrocarbons)
How to separate the crude oil— fractional distillation ?
• Crude oil is heated to boil and the vapors pass into a
fractionating column, which is cooler at the top and hotter
at the bottom
• The vapor will cool down when rising up the fractionating
column
• The vapor will condense into liquid when the temperature of
column is same to its condensation point (can be collected
and flow out)
• The rest of vapor will go up until it is condensed at its
condensation point
• Smaller molecules have lower boiling points and get further
up the column before they condense
• Longer chain hydrocarbons have higher boiling points and
condense lower down in the column
• Boiling point: Bitumen> Fuel oil> diesel oil> kerosene> gasoline> refinery gases
Environmental problems associated with the burning of fossil fuels?

1. Greenhouse gas: carbon dioxide, traps the heats radiated from the earth surface and leads to
climate changes, solution: use clean energy to replacing fossil fuels, wind energy, solar
energy…

2. Acid rain:
• Rain is naturally slightly acidic (pH=5.6)，acid rain has lower pH value (pH~4)
• formed when water and oxygen in the atmosphere react with SO2 to produce sulfuric acid
(main component of acid rain) or with various oxides of nitrogen-NOx to give nitric acid

4NO(g)+3O2(g)+2H2O(l)→4HNO3(aq)

• Acid rain has devastating effect on trees and lives

• Acid rain can rot the limestone buildings and marble statues (made of calcium carbonate)

• Solution: remove the sulfur from fuel, scrub the gases from power stations and factories to
remove SO2 and Nox, using catalytic converters in cars (change Nox to N2)
 homologous series: -(CH2)-, carbon number of
Cracking alkene formed >=2
• A process to break long-chain alkanes to alkenes and shorter-chain alkanes.

• Cracking is a thermal decomposition reaction and require high temperature:

big molecule splitting into smaller and more useful ones on heating.
• During cracking, C-C single bonds are broken and new C=C double bonds
are formed in a fairly random way
• Cracking produces a mixture of alkanes and alkenes

ethene propene Octane

Why oil companies carry out cracking?

Background for cracking of hydrocarbons

• Although most of the fractions from fractional distillation of crude oil are
useful as fuels, but
• Too many long-chain hydrocarbons are not in such high demand and are not as
profitable to sell
• There are not enough shorter-chain hydrocarbons used as fuels

• The reasons for carrying out Cracking

• Cracking can produce more useful and profitable products
• To make long-chain hydrocarbons to produce more petrol
• To produce more alkenes that can be used for making polymers (plastics)
Exercise