Retrosynthesis Practice Problems

The method of retrosynthetic analysis is very effective, but it requires a great knowledge of chemical compounds, classes of compounds, chemical reactions, reaction conditions etc.

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In general, having two ortho-, para-directing, electron-withdrawing groups in the reactant is sufficient to allow this sort of reaction to occur.

Now consider this retrosynthesis problem: The only solution is to first start with a halogen in the desired ipso position, as it is an ortho-, para-director and will allow you to add the NO electron-withdrawing groups, after which you can swap out the Cl for the CN: Note that the larger halogens Br and I don’t participate as well in this chemistry.

How would you make trans-1,2-pentadiol from pentan...

Part AWhich of the following reactions or series o...

In each reaction box, place the best reagent and ...

What is the starting material in the following rea...

F is actually better than Cl as a leaving group for this sort of substitution, however we do not know how to make fluorinated benzene, so here our only option was to use a chlorinated one.

Now consider this reaction: At first it seems to violate the rule we have just learned, that you need electron-withdrawing groups to enable nucleophilic aromatic substitution.

The target molecule is broken down into smaller and smaller fragments.

The actual synthesis can then be designed based on the retrosynthetic analysis.