1. 17.CARBOXYLIC ACIDS AND DERIVATIVES. ( approx. lecture time: 4 lectures) Topics covered: 17.1-17.2A-I,17.3-17.8,17.13. Some important carboxylic acids

2. Carboxylic Acids are Weak Acids pK a = 4.7 (vineger)

3. Nomenclature

5. Synthesis of Carboxylic Acids

6. Synthesis of Carboxylic Acids via Carboxylation

7. Addition-Elimination at the Acyl Carbon (explains > 95% of the chemistry) ORDER OF REACTIVITY: > R-CN Nitrile and acid

8. Interconversion of Carboxylic Acid Derivatives In principle, any carboxylic acid derivative can be converted to another. In practice, acid chlorides (RCOCl), being the most reactive, are best for making them all (except nitriles) interconversion between amide and nitrile: “acyl transfer” This reaction is also an “acyl transfer”

9. Acid anhydrides are next in reactivity, and these can be converted to esters and amides:

10. Esterification of Carboxylic Acids Forward reaction: Esterification Reverse reaction: Hydrolysis (Acids and esters have an intimate relationship)

11. Esterification and Hydroylsis Mechanisms Acid-catalyzed esterification and hydrolysis: Base-catalyzed hydrolysis:

12. Hydrolysis of Amides (Basis of peptide hydrolysis and protein digestion) Acid-catalyzed: Base-catalyzed:

13. Ask yourself what interconversions are possible, indicating the reagent required and then a reaction mechanism. You should know the ones in red ! Interconversion of Carboxylic Acid Derivatives

14. Some Important Amides Kevlar (Nomex is the meta isomer) Tylenol Penicillin Imodium (an opiod) LSD Capsaicin “bullet proof” vests