Illustrated Glossary of Organic Chemistry

Retrosynthesis (retrosynthetic analysis): The idea of working backwards from final target molecule to starting materials (usually via one or more intermediates) when designing a synthesis. The development of this thought process is widely attributed to E. J. Corey of Harvard University, who was awarded the 1990 Nobel Prize in Chemistry.

In this simple example of retrosynthetic analysis, tert-butanol (the target molecule) is envisioned to arise via hydrolysis of 2-bromo-2-methylpropane. (The hollow arrow pointing to the right indicates 'molecule on the left arises from molecule on the right' or 'molecule on the left can be synthesized from molecule on the right'.) 2-Bromo-2-methylpropane is, in turn, envisioned to arise from methylpropane via free radical bromination.

The reaction sequence for synthesis of tert-butanol from methylpropane, based on the retrosynthetic analysis above.