14. Synthesis of 1-Phenylacetone from Ethylbenzene

Adding a functional group to a benzylic position is easy, but what’s next?

This synthesis shows one important aspect of multi step synthesis problems ﹣ there are many possible answers! Which one is better? Well, it depends on what we qualify is “better” is this case. Better as in “less steps” is obvious and is what we typically go for. But occasionally, better might mean the use of a new reaction or a novel synthetic procedure you’ve just covered in class. Many instructors prefer when you use new material on the test when you’re doing your synthesis. So, keep this in mind.

Reactions that you’ll see in this synthesis are:

1. Radical halogenation
2. Elimination
3. Halogenation of alkenes
4. Reactions of alkynide ions
5. Hydroboration-oxidation of alkynes
6. Oxidation of alcohols