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Carboxylic Acid Derivatives

By James Ashenhurst

Summary Sheet #5 – 9 Key Mechanisms in Carbonyl Chemistry

Last updated: May 21st, 2019

I finally got around to putting together a summary sheet of the two previous series on mechanisms in carbonyl chemistry (anionic nucleophiles and neutral nucleophiles) It’s a companion piece to the summary sheet of the key reactions in carbonyl chemistry (otherwise known as the Big Freaking Grid).

The key point is that you can boil down all of the reactions on the Big Freaking Grid down to 9 key mechanistic steps. Five of them are particular to carbonyls:  [1,2]-addition, [1,2]-elimination, [1,4]-addition, [1,4]-elimination,  and keto enol tautomerism. A sixth is simply a function of the nucleophilicity of enolates and carboxylates (the SN2). And the remaining three are general to organic chemistry – protonation, deprotonation, and proton transfer. I realize that proton transfer is not mechanistically distinct from protonation/deprotonation, but since we’re so often fond of writing it as one step, I thought it deserved its own place.

I’d  appreciate any feedback on the inevitable typos/mistakes, as well as constructive suggestions for how to improve it.

Here it is: Key_Carbonyl_Mechanisms (PDF)

1-9 mechs-2015

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