Molecular and structural

formulae
Organic compounds can be represented by three main different types of formula:
empirical formulae, molecular formulae, and structural formulae. Each type of
formula provides different information about the organic compound it represents.
Structural formulae can be divided into full structural formulae, condensed
structural formulae and skeletal formulae. In this section, we will look at examples
of each type.

Empirical and molecular formulae

Empirical and molecular formulae were covered in section 1.2.3. Recall that
the empirical formula represents the simplest whole number ratio of atoms in a
compound. For some alkanes, methane and propane, for example, the empirical
formula is the same as the molecular formula. However, for other compounds, this is
not the case. For example, the empirical formula of ethane (C2H6) is CH3.

The molecular formula represents the actual number of each type of atom in a
compound. For example, butane has the molecular formula C4H10, ethanol has the
molecular formula C2H5OH and ethanoic acid has the molecular formula CH3COOH.
This represents the actual number of each type of atom in one molecule of the
compound. 

Structural formulae
In full structural formulae, all atoms and the bonds between the atoms are shown.
The full structural formula of butane (C4H10) is shown in Figure 1. Note that all the
carbon atoms and the hydrogen atoms are shown together with the bonds between the
atoms. In full structural formulae, a single line represents a single covalent bond, a
double line a double covalent bond and a triple line a triple covalent bond. 

Figure 1. The full structural formula of butane, C H

4 10

Sometimes it is preferable to use condensed structural formulae, in which the bonds

between atoms are omitted. For example, propane can be written as CH3CH2CH3, and
butane can be written either as CH3CH2CH2CH3 or as CH3(CH2)2CH3. 

In skeletal formulae, all atoms are omitted leaving only the backbone of the
molecule. In this type of formula, carbon atoms are assumed to be at the intersection
of each line and at the end of each line. In addition, hydrogen atoms bonded to carbon
atoms are not shown (recall that carbon can form four bonds so the number of
hydrogen atoms can be deduced from this). If hydrogen is part of a functional group
(such as a hydroxyl group, OH) it is shown. Figure 2 shows the skeletal formula of
propan-1-ol (CH3CH2CH2OH) with the carbon and hydrogen atoms omitted. 

Figure 2. Skeletal formula of propan-1-ol

Figure 3 shows the skeletal formula of but-2-ene (CH3CH=CHCH3) with the carbon-
to-carbon double bond represented by two lines. 

Figure 3. Skeletal formula of but-2-ene

Figure 4 shows the several different ways of representing the structure of the same
molecule, pentane (C5H12).

Figure 4. The different ways of

depicting the structure of a molecule. 

Representing formulae in 3-D

When representing organic molecules in two-dimensions, we use structural formulae
with 90° and 180° bond angles. However, this does not represent the actual molecular
geometry of the molecule. When carbon forms four single bonds, the molecular
geometry is tetrahedral with the bonds at 109.5° to each other. When it forms a double
bond, as in ethene, the arrangement is trigonal planar with a bond angle of 120°. For
certain molecules, it is useful to show the relative three-dimensional positions of
atoms or groups around a selected carbon atom, known as the stereochemical
formula. In a stereochemical formula, a bond sticking out from the plane of the page
(towards the viewer) is shown as a solid wedge, whereas a bond directed behind the
page (away from the viewer) is shown as a broken line (Figure 5). 

Figure 5. Methane and ethane have bond angles of

109.5  and 120  respectively.
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Exam tip

Make sure that you read exam questions carefully and know the difference when a question asks
you to name an organic compound, give its molecular formula, or when to draw its structural
formula. 

Branched and cyclic structures 

So far, we have only looked at alkanes with straight-chain structures that have no
branches from the main chain of carbon atoms. Figure 6 shows a model of the
alkane C7H16 which is a straight-chain alkane. Strictly speaking, it is not perfectly
straight due to the 109.5o bond angles between the carbon atoms. However, we still
refer to this type of structure as straight-chain as it is not branched (it has no
branches).  

Figure
6. The structure of a straight chain alkane, heptane (C H ).
7 16

Figure 7 shows the structural formula of 2,2,4-trimethylpentane, which is

a branched-chain alkane. The system for numbering the positions where the branches
attach to the main hydrocarbon chain will be outlined later - though if you look
closely at the molecule you can probably begin to work it out for yourself. 
 Fi
gure 7. 2,2,4-trimethylpentane is a branched-chain hydrocarbon. 
Carbon atoms can also be joined together in rings, forming cyclic alkanes (Figure
8). The structures of these cyclic hydrocarbon molecules are often represented by
polygons. The corners of the polygon represent a carbon atom together with the
hydrogen atoms that are bonded to the carbon.

Figure
8. Cyclic alkanes - cyclopropane, cyclobutane, cyclopentane and cyclohexane.
Section questions
 Complete this section with 2 questions.