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17. CARBOXYLIC ACIDS AND DERIVATIVES. ( approx. lecture time: 4 lectures)

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. Carboxylic Acids are Weak Acids. pK a = 4.7. ( vineger ). Nomenclature. Synthesis of Carboxylic Acids.

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17. CARBOXYLIC ACIDS AND DERIVATIVES. ( approx. lecture time: 4 lectures)

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  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 pKa = 4.7 (vineger)

  3. Nomenclature

  4. Synthesis of Carboxylic Acids

  5. Synthesis of Carboxylic Acids via Carboxylation using Grignard reagent

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

  7. 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) All acyl transfers This reaction is also an “acyl transfer” interconversion between amide and nitrile:

  8. Acid anhydrides are next in reactivity, and these can be converted to esters and amides: All acyl transfers

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

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

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

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

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

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