Most organic compounds are insoluble in water. But sometimes it’s necessary to make them dissolve, perhaps by converting them to anions or cations. Water can solvate both cations and anions, unlike some of the solvents you will meet later. A good way of dissolving an organic acid is to put it in basic solution: the base deprotonates the acid to give an anion. A simple example is aspirin: whilst the acid itself is not very soluble in water, the sodium salt is much more soluble. The sodium salt forms with the weak base, sodium hydrogen carbonate.

The sodium or calcium salt of ‘normal’ aspirin is sold as ‘soluble aspirin’. But when the pH of a solution of aspirin’s sodium salt is lowered, the amount of the ‘normal’ acidic form present increases and the solubility decreases. In the acidic environment of the stomach (around pH 1–2), soluble aspirin will be converted back to the normal acidic form and precipitate out of solution.

In the same way, organic bases such as amines can be dissolved by lowering the pH. Codeine (7,8-didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-ol) is a commonly used pain killer. Codeine itself is not very soluble in water but it does contain a basic nitrogen atom that can be protonated to give a more soluble salt. It is usually encountered as a phosphate salt. The structure is complex, but that doesn’t matter.

مواضيع ذات صلة

Heterocyclic aromatic compounds

Hückel’s rule tells us if compounds are aromatic

Molecular orbitals and aromaticity

The π molecular orbitals of other conjugated cyclic hydrocarbons

Benzene has six π molecular orbitals

Varying the number of electrons

Heats of hydrogenation of benzene and cyclooctatetraene

? What makes benzene special

Aromaticity

Conjugation and reactivity: looking forward to Chapter 10

The amide group

Delocalization over three atoms is a common structural feature The carboxylate anion