Carboxylic Acid Derivatives

[blonquich]

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Hey everybody,

This is a more general question regarding carboxylic acid derivatives. So I'm taking the TPR class and they have a whole bunch of stuff on all the different ways acid chlorides, esters, etc. react with each other. I'm also using EK as a secondary source, which goes into much less detail. It pretty much just lays out reactions for acid chlorides and esterification.

I was wondering if someone could give me the gist of what exactly I need to be familiar with. Princeton is notorious for going into too much detail, and with 3 weeks to go, I can't afford to be memorizing things I don't need to.

Let me know if you have any suggestions, thanks!

Brian

 

[StIGMA]

Most important thing is reactivity.

Acid chlorides > acid anhydrides > esters > amides ~= carboxilic acids

So an acid chloride can be hydrated by nucleophilic substitution into an ester (by an alcohol) or an amide (by an amine) but an amine cannot be turned into an acid chloride. Carb acids can go in the reverse direction under stricter conditions.

Basically know what is more reactive, and general reaction mechanisms. ALL of these undergo ONE reaction mechanism (nuc substitution), and you should be able to figure out leaving group/what is substituted fairly easily.

Also know how to form each of these from the simpler derivatives (ie: carb acids).