MODULE 1.

THE CHEMISTRY OF
CARBON COMPOUNDS
TOPIC: Structure and Formulae

Learning Outcomes
1.1 Explain the occurrence of carbon
compounds with straight chains,
branched chains and rings
1.2 Explain the meaning of the term
“homologous series”
1.3 Distinguish between empirical,
molecular and structural formula
 MODULE 1. THE CHEMISTRY OF
CARBON COMPOUNDS
TOPIC: Structure and Formulae

• The ability of carbon to form big molecules has

enabled nature to form living matter, from simple cells
to complex tissues.

• Gasoline or petrol is a mixture of hydrocarbons and is

used primarily as fuel in internal combustion engines
of cars.
 WHY CARBON IS THE UNIQUE THAT IT
FORMS A LARGE VARIETY OF COMPOUNDS?
Carbon atom:
• is tetravalent
• has the ability to bond with other
(catenation)
• has the ability to mix and rearrange the
four orbitals in the outer shell
(hybridization) e.g. sp3, sp2, sp.
• has resonance (delocalized electrons)
 Carbon atoms are able to form a few types of
covalent bonds with other carbon atoms or atoms of
other elements:

• Single bonds: C-C, C-H, C-O, C-X (X = halogens))

• Double bonds: C=C, C=O

• Triple bonds: C≡ C, C≡N

• Organic compounds can be classified as

unbranched, branched or ring compounds.
 Straight (unbranched) Chain Compounds

• Straight-chain molecules that are unbranched

may contain single, double or triple bonds. E.g.:

Single bond Double bonds

Triple bonds
 Branched- Chain Compounds

• Branched chain compounds consist of

one or more carbons of a straight chain
compound forming bonds with more than
two carbons.
 Ring Chain Compounds

• Ring chain compounds consist of a ring of carbon

atoms
There are five types of formulae which can be
used to describe and identify organic
compounds:

1. Molecular formula
2. Empirical formula
3. Full structural or displayed formula
4. Condensed structural formula
5. General formula
Homologous Series
A homologous series is a group or family of
organic compounds that has the following
characteristics:
- the same general formula.
- similar chemical properties because they have
the same functional group.
- each member differs from the previous one by
-CH2.
- show a gradual change in density, viscosity,
flammability, melting point and boiling point.
 Functional group

is that atom or group of atoms in

an organic molecule whose reaction
determines its overall chemical
properties.
Complete the table given below:

Condensed Display
Molecular
Name Structural Structural
Formulae
Formulae Formula

Butane
C4H10 CH3CH2CH2CH3
Methylpropane
C4H10 CH3CH(CH3)CH3
Ethanol C2H5OH CH3CH2OH
Hexan-1-ol C6H13OH CH3(CH2)4CH2OH
cyclopentane
C5H1O
Ethanoic acid
C2H4O2 CH3COOH
MODULE 1. THE CHEMISTRY OF
CARBON COMPOUNDS
TOPIC: Naming Organic Compounds

Learning Outcomes

1.5. write structural formulae

1.6. apply the IUPAC rules to name

organic compounds
IUPAC RULES TO NAME ORGANIC COMPOUNDS
1. Identify the longest carbon chain. This chain is
called the parent chain.
2. Identify all of the substituents (groups
appending from the parent chain).
3. Number the carbons of the parent chain from
the end that gives the substituents the lowest
numbers.
4. If the same substituent occurs more than once,
the location of each point on which the
substituent occurs is given. In addition, the
number of times the substituent group occurs
is indicated by a prefix (di, tri, tetra, etc.).
IUPAC RULES TO NAME ORGANIC COMPOUNDS
5. If there are two or more different substituents they are
listed in alphabetical order using the base name (ignore
the prefixes).

6. If chains of equal length are competing for selection as

the parent chain, then the choice goes in series to:
a) the chain which has the greatest number of side chains.
b) the chain whose substituents have the lowest- numbers.
c) the chain having the greatest number of carbon atoms
in the smaller side chain.
d)the chain having the least branched side chains.

7. A cyclic (ring) hydrocarbon is designated by the prefix

cyclo- which appears directly in front of the base name.
Principle •The principle functional group is used to define the class the
Functional group compound belongs to e.g. an alcohol, ROH
•The principle functional group is the highest priority functional
group.
•The principle functional group is usually given the lowest locant
possible.
Longest chain •The longest continuous chain containing the principle functional
group defines the root name.
•Other groups attached to this chain are called substituents.
•If there are two chains of equal length, then the choice that gives
the simplest substituents is chosen.
Numbering •The numbers that define the positions of the principle functional
(i.e. assigning group and substituents are called locants.
locants) •Compounds are numbered from one end of the longest
continuous chain.
•The locants are assigned such that the principle functional group
gets the lowest possible locant.
•If this results in a "tie" then the first point of difference rule is
applied so that the first time a difference in numbering occurs, then
the method that gives the lower number at this first difference is
used.
•In the event that there is no first point of difference then
alphabetisation is used.
 EXAMPLES
Here are some examples:
MODULE 1. THE CHEMISTRY OF
CARBON COMPOUNDS
TOPIC: STRUCTURAL ISOMERISM

Learning Outcomes

1.7. Define with examples, structural

isomerism

1.9. determine the possible isomer

from given molecular formulae
 Structural Isomerism
Structural Isomers are organic compounds
with the same molecular formula but
different structural formulae.
Isomers that are in the same homologous series have
similar chemical properties but differ slightly in melting points
and boiling points.

Isomers of butane (C4H10)

Structural isomers are classified as:

1. Chain isomers: have different arrangement

of carbon chains, but belong to the same
homologous series.
2. Positional isomers: have functional groups
located at different positions on the same
carbon skeleton and belong to the same
homologous series.
3. Functional group isomers: have different
functional group and belong to different
homologous series
 the chain is branched.

CHAIN ISOMERS
 middle.

POSITIONAL ISOMERS
 (an aldehyde) orester).
propanone (a ketone).

FUNCTIONAL GROUP ISOMERS

1. Are the compounds given below isomers?
Explain why.

2. Write the condensed structural formula of three

isomers of
(a) hexene
(b) butan-1-ol
MODULE 1. THE CHEMISTRY OF
CARBON COMPOUNDS
TOPIC: STEREOISOMERISM
Learning Outcomes

1.8. explain stereoisomerism

1.9. determine the possible isomers

from given molecular formulae
 Stereoisomers: have the same molecular
formula and also the same structural
formula. The difference between them is
arrangement of the bonds in space.
- GEOMETRIC OR CIS-TRANS ISOMERS:
compounds with double bond shows
restriction of rotation about the C=C.

- OPTICAL ISOMERS: have the ability to rotate the

plane of polarized light. It must possess
at least one asymmetric carbon atom
(chiral).A sample which contains a chiral
carbon atom and is optically inactive is
called a racemic mixture.
happens if you have a carbon-carbon
on thisdouble
side")bond - as in 1,2-dichloroethene?

GEOMETRIC OR CIS-TRANS ISOMERS

To get geometric isomers you must have:

restricted rotation (often involving a carbon-

carbon double bond for introductory
purposes);
two identical groups attached to adjacent
carbon atom
 two different groups attached to each
carbon on the double bond
Where there are four groups attached, there is no symmetry anywhere in the molecule.

OPTICAL ISOMERS
Simple substances which show optical
isomerism exist as two isomers known
as enantiomers.

Where there are four groups attached, there is no

symmetry anywhere in the molecule.
A molecule which has no plane of
symmetry is described as chiral.

The carbon atom with the four different

groups attached which causes this lack
of symmetry is described as a chiral
centre or as an asymmetric carbon
atom.
 star.

The asymmetric carbon atom in

a compound (the one with four
different groups attached) is
often shown by a star.
 image.

The mirror image.

The two enantiomers are
When optically active substances are made
in the lab, they often occur as a 50/50
mixture of the two enantiomers.
This is known as a racemic mixture or
racemate. It has no effect on plane
polarised light
 for butan-2-ol.

Identifying chiral centres

in skeletal formulae for
butan-2-ol.