8.3 Structural Representations of Organic Compounds

Complete, Condensed and Bond-line Structural Formulas

Structures of organic compounds are represented in several ways. The Lewis structure or dot structure, dash structure, condensed structure and bond line structural formulas are some of the specific types. The Lewis structures, however, can be simplified by representing the two-electron covalent bond by a dash (-). Such a structural formula focuses on the electrons involved in bond formation. A single dash represents a single bond, double dash is used for double bond and a triple dash represents triple bond. Lonepairs of electrons on heteroatoms (e.g., oxygen, nitrogen, sulphur, halogens etc.) may or may not be shown. Thus, ethane \(\left(\mathrm{C}_2 \mathrm{H}_6\right)\), ethene \(\left(\mathrm{C}_2 \mathrm{H}_4\right)\), ethyne \(\left(\mathrm{C}_2 \mathrm{H}_2\right)\) and methanol \(\left(\mathrm{CH}_3 \mathrm{OH}\right)\) can be represented by the following structural formulas. Such structural representations are called complete structural formulas.

These structural formulas can be further abbreviated by omitting some or all of the dashes representing covalent bonds and by indicating the number of identical groups attached to an atom by a subscript. The resulting expression of the compound is called a condensed structural formula. Thus, ethane, ethene, ethyne and methanol can be written as:
\(
\begin{array}{lllr}
\mathrm{CH}_3 \mathrm{CH}_3 & \mathrm{H}_2 \mathrm{C}=\mathrm{CH}_2 & \mathrm{HC} \equiv \mathrm{CH} \quad \quad \quad \mathrm{CH}_3 \mathrm{OH} \\
\text { Ethane } & \text { Ethene } & \text { Ethyne } \quad \quad \quad \quad \text { Methanol }
\end{array}
\)

Similarly, \(\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CH}_2 \mathrm{CH}_2 \mathrm{CH}_2 \mathrm{CH}_2 \mathrm{CH}_2 \mathrm{CH}_3\) can be further condensed to \(\mathrm{CH}_3\left(\mathrm{CH}_2\right)_6 \mathrm{CH}_3\). For further simplification, organic chemists use another way of representing the structures, in which only lines are used. In this bond-line structural representation of organic compounds, carbon and hydrogen atoms are not shown and the lines representing carbon-carbon bonds are drawn in a zig-zag fashion. The only atoms specifically written are oxygen, chlorine, nitrogen etc. The terminals denote methyl \(\left(-\mathrm{CH}_3\right)\) groups (unless indicated otherwise by a functional group), while the line junctions denote carbon atoms bonded to appropriate number of hydrogens required to satisfy the valency of the carbon atoms. Some of the examples are represented as follows:

(i) 3-Methyloctane can be represented in various forms as:

(ii) Various ways of representing 2-bromo butane are:

In cyclic compounds, the bond-line formulas may be given as follows:

Example 8.4: Expand each of the following condensed formulas into their complete structural formulas.
(a) \(\mathrm{CH}_3 \mathrm{CH}_2 \mathrm{COCH}_2 \mathrm{CH}_3\)
(b) \(\mathrm{CH}_3 \mathrm{CH}=\mathrm{CH}\left(\mathrm{CH}_2\right)_3 \mathrm{CH}_3\)

Answer: 

Example 8.5: For each of the following compounds, write a condensed formula and also their bond-line formula.
(a) \(\mathrm{HOCH}_2 \mathrm{CH}_2 \mathrm{CH}_2 \mathrm{CH}\left(\mathrm{CH}_3\right) \mathrm{CH}\left(\mathrm{CH}_3\right) \mathrm{CH}_3\)
(b)

Answer:

Condensed formula:
(a) \(\mathrm{HO}\left(\mathrm{CH}_2\right)_3 \mathrm{CH}\left(\mathrm{CH}_3\right) \mathrm{CH}\left(\mathrm{CH}_3\right)_2\)
(b) \(\mathrm{HOCH}(\mathrm{CN})_2\)

Bond-line formula:

Example 8.6: Expand each of the following bond-line formulas to show all the atoms including carbon and hydrogen

Answer: 

Three-Dimensional Representation of Organic Molecules

The three-dimensional (3-D) structure of organic molecules can be represented on paper by using certain conventions. For example, by using solid and dashed wedge formula, the \(3-\mathrm{D}\) image of a molecule from a two-dimensional picture can be perceived. In these formulas the solid-wedge is used to indicate a bond projecting out of the plane of paper, towards the observer. The dashed-wedge is used to depict the bond projecting out of the plane of the paper and away from the observer. Wedges are shown in such a way that the broad end of the wedge is towards the observer. The bonds lying in plane of the paper are depicted by using a normal line (-). 3-D representation of methane molecule on paper has been shown in Fig. 8.1

Molecular Models

Molecular models are physical devices that are used for a better visualisation and perception of three-dimensional shapes of organic molecules. These are made of wood, plastic or metal and are commercially available. Commonly three types of molecular models are used: (1) Framework model, (2) Ball-and-stick model, and (3) Space filling model. In the framework model only the bonds connecting the atoms of a molecule and not the atoms themselves are shown. This model emphasizes the pattern of bonds of a molecule while ignoring the size of atoms. In the ball-and-stick model, both the atoms and the bonds are shown. Balls represent atoms and the stick denotes a bond. Compounds containing \(\mathrm{C}=\mathrm{C}\) (e.g., ethene) can best be represented by using springs in place of sticks. These models are referred to as ball-and-spring model. The space-filling model emphasises the relative size of each atom based on its van der Waals radius. Bonds are not shown in this model. It conveys the volume occupied by each atom in the molecule. In addition to these models, computer graphics can also be used for molecular modelling.