Be realistic Below is another organic structure—again, you may be familiar with the molecule it repre- sents; it is a fatty acid commonly called linoleic acid.

We could also depict linoleic acid as

You may well have seen diagrams like these last two in older books—they used to be easy to print (in the days before computers) because all the atoms were in a line and all the angles were 90°. But are they realistic? We will consider ways of determining the shapes and structures of molecules in more detail in Chapter 3, but the picture below shows the structure of linoleic acid determined by X-ray crystallography.

You can see that the chain of carbon atoms is not linear, but a zig-zag. Although our diagram is just a two-dimensional representation of this three-dimensional structure, it seems reason able to draw it as a zig-zag too.

This gives us our fi rst guideline for drawing organic structures.

Realism of course has its limits—the X-ray structure shows that the linoleic acid molecule is in fact slightly bent in the vicinity of the double bonds; we have taken the liberty of drawing it as a ‘straight zig-zag’. Similarly, close inspection of crystal structures like this reveals that the angle of the zig-zag is about 109° when the carbon atom is not part of a double bond and 120° when it is. The 109° angle is the ‘tetrahedral angle’, the angle between two vertices of a tetrahedron when viewed from its centre. In Chapter 4 we shall look at why carbon atoms take up this particular arrangement of bonds. Our realistic drawing is a projection of a three-dimensional structure onto flat paper so we have to compromise.

مواضيع ذات صلة

Curly arrows show the movement of electrons

Curly arrows represent reaction mechanisms

Identifying an electrophile

Nucleophiles and electrophiles

Orbital overlap is essential for successful reaction

Reactions happen when electrons flow between molecules

Orbital overlap brings molecules together

Charge attraction brings molecules together

Not all collisions between molecules lead to chemical change

Chemical reactions

Rotation and rigidity

The carbonyl group