Organic Chemistry

Learning outcomes
You should be able to:
• Interpret, name and use the general, structural, displayed and skeletal formulae of the alkanes,
alkenes, alcohols and carboxylic acids.
• Understand and use the following terminology associated with organic chemistry:
✓ Saturated and unsaturated
✓ Functional group
✓ Homologous series
✓ Addition, substitution
✓ Cracking
✓ Polymerisation
• Understand the chemical behaviour of alkanes, alkenes, alcohols and carboxylic acids.
• Describe the test to distinguish between saturated and unsaturated hydrocarbons
• Suggest how cracking can be used to obtain more useful alkanes and alkenes of lower Mr
• Understand polymerisation and identify monomers and repeat units in polymers
• Describe the environmental consequences of burning hydrocarbons
• Describe the reaction of a carboxylic acid with an alcohol using an acid catalyst to form an ester
Organic Chemistry: What is it?
Organic chemistry is the study of the compounds of carbon (there are some inorganic carbon
compounds as well). There are more organic compounds than all the other compounds put
together.

These compounds include naturally occurring ones that are found in our bodies, for example;
• Proteins
• DNA
• Fats
There are also artificially made compounds such as plastics, dyes and drugs.
Organic Chemistry: What is it?
There are millions of different organic compounds. They all contain carbon and hydrogen, and
often other elements such as oxygen, nitrogen and chlorine. Carbon atoms can join together to
form chains and rings, which is why there are so many carbon compounds.

What do caffeine, aspirin and dyes have in common? They are all organic
compounds.
Organic Chemistry: What is it?
Organic chemistry is the study of carbon-containing compounds. Carbon is unique in the
variety of compounds it can form.

Special Features of Carbon

• CARBON ATOMS FORM STRONG COVALENT BONDS TO EACH OTHER
• THE CARBON ATOMS IN A CHAIN CAN BE LINKED BY SINGLE, DOUBLE OR
TRIPLE COVALENT BONDS
• CARBON CAN BE ARRANGED IN;
✓ STRAIGHT CHAINS
✓ BRANCHED CHAINS
✓ RINGS
• OTHER ATOMS/GROUPS OF ATOMS ARE PLACED ON CARBON ATOMS
Special features of Carbon
Organic Chemistry: What is it?
The term ‘organic’ was originally used because it was believed that organic
compounds could only come from living things. Now it is used for any carbon
compound except for the very simplest (like carbon dioxide, carbon monoxide,
the carbonates and the hydrogen carbonates).

Organic chemistry is the study of the structure, properties, composition,

reactions, and preparation of carbon-containing compounds. Most organic
compounds contain carbon and hydrogen, but they may also include any number
of other elements (e.g., nitrogen, oxygen, halogens, phosphorus, silicon, sulfur).
Classes of organic compounds

Class Members

Hydrocarbons Alkanes, Alkenes, Alkynes, Arenes

Halogen-containing compounds Alkyl halides, Aryl halides

Oxygen-containing compounds Alcohols, phenols, ethers,

aldehydes and ketones, carboxylic
acids
Carboxylic acid derivatives Esters, amides

Nitrogen-containing compounds Amines, nitriles, nitro compounds

 Hydrocarbons
Compounds that contain carbon and hydrogen only.
Examples: Alkanes, Alkenes, Alkynes
Examples of Hydrocarbons
Homologous series
A homologous series is a family of similar compounds with similar chemical properties
due to the presence of the same functional group.
Examples:

A homologous series is therefore a group of organic compounds which:

• Differ from each neighbouring member by a –CH2 group
• Have the same general molecular formula
• Have similar chemical properties because they have the same functional group
• Exhibit a gradual change along the series in physical properties such as boiling point, density
and solubility.
Homologous series

The reason that the alkanes and other homologous series can be described by a general
formula is that each member differs from the next by a –CH2– unit.
Homologous series
ALKANES ALKENES

CH4
C2H6 C2H4
C3H8 C3H6
C4H10 C4H8
C5H12 C5H10
The molecules differ from each other by a –CH2 group.
Functional groups
A functional group is an atom or group of atoms that determine the chemical properties of
a homologous series.
Different classes of compounds have different functional groups. The functional group
determines the characteristic chemical properties of the compounds that contain that specific
functional group.
The functional group in an alkene is the C꞊C double bond.
The function group in an alkyne is the C≡C triple bond.
Functional groups
Functional groups
All compounds in the same homologous series have the same functional group.
For example, the functional group for alcohols is the –OH group and that for
alkenes is C=C.
TYPES OF FORMULA FOR ORGANIC MOLECULES
Empirical formula
• An empirical formula tells you the simplest whole number ratio of the
atoms in a compound. It can be calculated from experimental data.
• Without more information, it is not possible to identify the ‘true’ or ‘molecular’
formula.
• Sometimes the empirical formula is the same as the molecular formula.
• For example, the empirical formula of methane is CH4, which is the same as its
molecular formula.
• However, the empirical formula of ethane is CH3 whereas its molecular formula
is C2H6.
TYPES OF FORMULA FOR ORGANIC MOLECULES
Molecular formula
• A molecular formula counts the actual number of each type of atom present in a
molecule.
• For example, the molecular formula of butane is C4H10 and the molecular formula of
ethene is C2H4.
• The molecular formula is a multiple of the empirical formula.
• For example, if a compound has empirical formula CH2, the molecular formula could
be C2H4, C3H6, C4H8 etc. The ratio of C:H must always be the same as in the empirical
formula.
• The molecular formula tells you nothing about the way the atoms are joined together.
• Molecular formulae are used very rarely in organic chemistry because they don’t give
any useful information about the bonding in the molecule. You might use them in
equations for the combustion of simple hydrocarbons, where the structure of the
molecule doesn’t matter.
• In almost all other cases, you use a structural or a displayed formula.
TYPES OF FORMULA FOR ORGANIC MOLECULES
Structural formula
• A structural formula shows how the atoms in a molecule are joined together.
• They can be written out in condensed form (condensed structural formula) by
omitting all the carbon–carbon single bonds and carbon–hydrogen single bonds,
for example CH3CH2CH3. You need to be confident about using either way.
• The structural formula for butane can be shown as

These both show exactly how the atoms in the molecule are joined together.
The corresponding molecular formula, C4H10, doesn’t give you the same
sort of useful information about the molecule.
TYPES OF FORMULA FOR ORGANIC MOLECULES
Structural formula

All three structures represent butane. The convention is to write the structure with
all the carbon atoms in a straight line.
Each structure shows four carbon atoms joined together in a chain, but the chain
has simply twisted. This happens in real molecules as well.
TYPES OF FORMULA FOR ORGANIC MOLECULES
Structural formula

These diagrams show the shape of a butane molecule better, but you
would not draw these in an exam.

The atoms can rotate around single carbon–carbon bonds.

TYPES OF FORMULA FOR ORGANIC MOLECULES
Structural formula
A molecule like propene, C3H6, has a carbon–carbon double bond. This is shown
by drawing two lines between the carbon atoms to show the two pairs of shared
electrons. You would normally write this in a simplified structural formula as
CH3CH=CH2.
TYPES OF FORMULA FOR ORGANIC MOLECULES
Displayed formula
• A displayed formula (sometimes called a full structural formula) shows all
the bonds in the molecule as individual lines.
• You need to remember that each line represents a pair of shared electrons in a
covalent bond.
• Displayed formulae are always drawn with the
molecule straightened out and flattened.

• They do, however, show exactly how all the atoms

are joined together.

It is important to remember when you draw

Butane structures that C always forms four bonds and
H always forms one bond. Oxygen will form
two bonds and a halogen (chlorine, bromine
Propene
etc.) atom one.