Organic Chemistry Retrosynthesis

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Retrosynthesis or retrosynthetic analysis is a strategy for planning an organic synthesis by disconnecting a target molecule into precursor materials.

This steps are repeated until available starting materials are reached.

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

Retrosynthetic analysis is a technique for solving problems in the planning of organic syntheses.

Starting from an alkyne, remember that each double bond represents the presence of a pi bond that can be formed from an elimination reaction.

So, think “what can we eliminate that would have resulted in pi bond formation?

Below you will find online available information resources on retrosynthesis and retrosynthetic analysis. Barone, Cycle Chimie Fine, juin 2001 - [f] Retrosynthesis Tutorial...

will allow you to practice retrosynthetic analysis using the target molecule below.

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.


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