Retrosynthesis Practice Problems

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

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

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.

Draw the best alkene reactant that would give the ...

Propose a strategy to prepare the target as one of...

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