MODULE 1.

THE CHEMISTRY OF CARBON COMPOUNDS

TOPIC: Structure and Formulae

C. Bailey Polack
 Objectives:
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 IS CARBON UNIQUE THAT IT FORMS A LARGE
VARIETY OF COMPOUNDS?
Carbon atom:
• is tetravalent- this means it has four electrons
on its outermost shell that can take part in covalent
bonding .

• Shows catenation- this means it has the ability

to bond with other carbon atoms in chain or
ringed structures
• Undergoes hybridization -which is the ability to
mix and rearrange the four orbitals in the
outer shell e.g. sp3, sp2, sp.

• has resonance (delocalized electrons)

• (two or more structures of the same molecule
that differ only in the distribution/position of
the electrons.
• For a resonance structure to exist the molecule
must atleast one pi bond , the molecules must
have at least one of the following
• A) an atom with atleast one lone pair.
• B) an allylic group ( carbon atom bonded to
another carbon atom that has a double bond)
 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 Double
bond 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
 Formulae which can be used to describe and
identify organic compounds:
1. Molecular formula:
The formula which shows the actual number of each type of
atom
» Covalent compounds are represented by molecular formula

2. Empirical formula
shows the simplest whole number ratio of atoms or ions of
each element in a compound (molecule or formula unit)
– Ionic compounds are always represented by empirical
formulae
3. Full structural or displayed formula
show all the covalent bonds and atoms
present in a molecule
4. Condensed structural formula
shows the minimal detail that shows the arrangement of atoms in a
molecule, eg for butane:CH3CH2CH2CH3 or CH3(CH2)2CH3,
5. General formula
algebraic formula for a homologous series e.g. CnH2n

6. Skeletal formula
shows the simplified organic formula, shown by removing hydrogen
atoms from alkyl chains, leaving just a carbon skeleton and
associated functional groups
Skeletal Formula
 Complete the table given below:

Condensed Structural Display Structural

Name Molecular 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
 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.
 TOPIC: Empirical and Molecular formula
Learning Outcomes

1.4. determine formulae (empirical & molecular)

from experimental data [combustion analysis]
 Recall Chemical Formulae

• Chemical formulae can be written in two main ways:

– The Empirical Formula - gives the simplest whole number mole
ratio between the atoms or ions present in the compound
(molecule or formula unit)
• Ionic compounds are always represented by empirical formulae

– The Molecular formula – gives the actual number of moles of

atoms of each element present in one mole of the compound
• Covalent compounds are represented by molecular formula
 Chemical Formulae
• Many inorganic molecules have the same empirical and molecular formulae.

• Many organic molecules have different empirical and molecular formulae.

SOME EMPIRICAL AND MOLECULAR FORMULA

Compound Empirical Formula Molecular Formula

Hydrogen Peroxide HO H2O2
Butane C2H5 C4H10
Benzene CH C6H6
Sulphur Dioxide SO2 SO2
Cyclohexane CH2 C6H12
Glucose CH2O C6H12O6

» Table 1
 Deducing an Empirical Formula

• If the proportions of the elements by mass, in a

compound are known, then its empirical formula
can be determined.

• If the molecular formula is different from the

empirical formula and the relative molecular
mass or molar mass is known, the molecular
formula can be determined
 Worked Question
• When analysed, a compound of mass 50.0 was
found to contain 18.3g of sodium, 12.7g of
sulphur and an unknown mass of oxygen.
Determine the empirical formula of the
compound.
 Worked Example
• When analysed, a compound of mass 50.0 was found to contain 18.3g of
sodium, 12.7g of sulphur and an unknown mass of oxygen. Determine the
empirical formula of the compound.
– Mass of oxygen in the compound
• = 50g – (18.3 + 12.7)g = 19.0g
Na S O
Mass 18.3g 12.7g 19.0g
Molar mass 23g/mol 32g/mol 16g/mol
# of moles 18.3 / 23 = 0.796 12.7/32 = 0.397 19.0/16 = 1.188
mol mol mol
Simplest mole 2 mol 1 mol 3 mol
ratio

– Empirical formula is Na2SO3

 Worked Question:
• Calculate the empirical formula of a compound of
carbon, hydrogen and iodine which contains 8.45%
carbon, 2.11% hydrogen and 89.44% iodine by mass.
(Ar values: C = 12, H = 1, I = 127)
 Worked Example
• Calculate the empirical formula of a compound of carbon,
hydrogen and iodine which contains 8.45% carbon, 2.11% hydrogen
and 89.44% iodine by mass. (Ar values: C = 12, H = 1, I = 127)
C H I
Mass % 8.45% 2.11% 89.44%
Mass in 100g 8.45g 2.11g 89.44g
Molar mass 12g/mol 1g/mol 127g/mol
# of moles 8.45/12 = 0.704 2.11/1 = 2.11mol 89.44/127
mol =0.704mol
Simplest mole 1 3 1
ratio

– Empirical Formula: CH3I

 Tips (Simplest Whole Number Ratio)
• You may be left with figures (ratios) that are not whole
numbers
– E.g. P=1, O=2.5
– In this case you must multiply up to get a whole number (in this
case by 2)
– So the formula = P2O5

• You may be left with a ratio such as

P = 1, O = 1.46
– It is advisable to round up the 1.46 to 1.5 then multiply up to get
a whole number (in this case by 2)
– Empirical formula : P2O3
 Tips (Simplest Whole Number Ratio)
You may be left with a ratio such as
⮚0.5
• Multiply by 2
⮚0.333
• Multiply by 3
⮚0.25
• Multiply by 4
⮚0.2
• Multiply by 5
⮚0.4
• Multiply by 5
 Deducing the molecular Formula

• To deduce the molecular formula

we need to know:
– The empirical formula
– The molar mass of the compound
– The empirical formula mass
 Worked example

• On analysis, a compound was

found to contain 54.5% carbon,
9.1 % hydrogen and 36.4%
oxygen. Determine the molecular
formula of this compound if its
relative molecular mass was 88
 Worked Example
• On analysis, a compound was found to contain 54.5% carbon, 9.1 % hydrogen
and 36.4% oxygen. Determine the molecular formula of this compound if its
relative molecular mass was 88
C H O
Mass in 100g 54.5g 9.1g 36.4g
Molar mass 12g/mol 1g/mol 16g/mol
# of moles 54.5/12 = 4.542 9.1/1 = 9.1mol 36.4/16 =
mol 2.2475mol
Simplest mole 2 mol 4 mol 1 mol
ratio

• Empirical Formula is C2H4O

• Relative molecular mass of the empirical formula -C2H4O = 44
• Relative molecular mass of the compound = 88
• Ratio between relative molecular masses = 88/44 =2
• Therefore the molecular formula is 2 times the empirical formula = C4H8O2
 Chemical Formulae (Combustion Analysis)
• A compound consists of only carbon and hydrogen.
13.75g of CO2 and 6.742g of H2O are formed during
the complete combustion of the compound.
– What is the empirical formula of the unknown
compound?

Remember
– You need to find the moles of each element in the
compound
– Then, find the simplest mole ratio of the elements
 Try

• A compound consists of only carbon hydrogen and

oxygen. 8.272g CO2 and 4.515g of H2O are produced
during the complete combustion of 3.765g of the
compound.
a) What is the empirical formula of the compound?
b) What is the molecular formula of the compound if the
molar mass of the compound is 300.47g/mol
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 (location)
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.
 IUPAC RULES TO NAME ORGANIC COMPOUNDS

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

prefix cyclo- which appears directly in front of
the base name.
Principle Functional
group •The principle functional group is used to define the class the 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
(i.e. assigning locants)
•The numbers that define the positions of the principle functional group and
substituents are called 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
Which of the chain is branched.

CHAIN ISOMERS
POSITIONAL ISOMERS
FUNCTIONAL GROUP ISOMERS

(an aldehyde) or
propanone (a ketone).

(ester).
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.
What happens if you have a carbon-carbon double 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
 ALSO
Alkenes that exhibit a CIS / TRANS type of
isomerism is called
Recall E-Z stereoisomerism
E-Z stereoisomers arise when:

(a) There is restricted rotation around the C=C

double bond.
(b) There are two different groups/atoms attached
both ends of the double bond.
 Naming E-Z stereoisomers

Priority Group: The atom (or specie) with the bigger

atomic number or mass is classified as the priority group
Naming E-Z stereoisomers
 CIS (Z) OR TRANS (E)?
priorit
priorit
y
y

priorit
y

priorit
y
The effect of EZ stereoisomerism on physical properties
E-Z stereoisomers can have differing melting and boiling points .
 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.
 The asymmetric carbon atom in a
compound (the one with four different
groups attached) is often shown by a star.
star.
The mirror image.
The two enantiomers are

image.
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
Identifying chiral centres in skeletal formulae
for butan-2-ol.