The Michael Reaction

by Kiley Lynch

What do you get when you use an enolate in a conjugate addition reaction?

The Michael reaction is a 1,4-addition (conjugate addition) of enolates to an alpha-beta unsaturated alkene.

It’s no different from the conjugate additions I talked about yesterday. The only thing is that when the nucleophile is an enolate, it’s called “The Michael Reaction”.

That’s the thing about organic chemistry… so many names, right? But the pattern is exactly the same.

We’re forming a C-C bond, and we’re breaking a C-C Pi bond. After we do the addition, we form an enolate – so adding acid gives us the neutral product.

Now, the thing is, it doesn’t matter what enolate you use – it could be the enolate from an ester, a ketone, a diketone, a diester – doesn’t matter. All those enolates work as nucleophiles. Same reaction.

It can be easy to get distracted by all the different combinations, because they all “look” so different. But they aren’t. The patterns of bonds formed and bonds broken is always the same for a given reaction. Don’t get distracted by the groups on the side.

Tomorrow: another reaction that is just going to be a *combination* of two reactions we already know.

Thanks for reading! James

P.S. Reaction Guide – the Michael Reaction