Chapter 20: Carboxylic Acid Derivatives. Learning Goals.

  1. You can provide a proper, unique name for a carboxylic acid derivative, given its structure. This includes acid chlorides, anhydrides, esters, amides and nitriles.
  2. You can draw a correct structure for any of these carboxylic acid derivatives, given its name.
  3. You know the characteristic peaks that appear in the IR spectra of different carboxylic acid derivatives.
  4. You know the general mechanism for nucleophilic acyl substitution, and can apply this mechanism in a way to predict relative reactivities of the different acid derivatives.
  5. You know how carboxylic acids can be converted to acid chlorides, anhydrides, esters or amides.
  6. You know how acid chlorides can be converted to carboxylic acids, esters, amides, anhydrides, ketones, aldehydes or alcohols.
  7. You know how anhydrides can be converted to carboxylic acids, esters or amides.
  8. You know how esters can be converted to carboxylic acids, other esters, amides or alcohols.
  9. You know how amides are converted to carboxylic acids, amines or nitriles..
  10. You know how nitriles can be hydrolyzed to amides or to carboxylic acids, and how Grignard reagents can convert nitriles to ketones.
  11. You know the role of fatty acid esters in waxes, fats and oils.
  12. You know how step-growth polymerization is used to form polyamides (Nylon) and polyesters.
Additional background on rearrangements (Wikipedia): Hofmann (covered in the text also), Curtius, Schmidt and Beckmann rearrangement reactions. Note the mechanistic similarities to carbocation rearrangements, the oxidation of trialkylboranes, and the Baeyer-Villiger reaction.

For those of you interested in biochemistry: Trypsin and how it cleaves amide bonds under mild biologic conditions.
Recommended problems: 
20.30    20.33    20.34    20.39    20.44    20.45    20.47
    20.48   20.53    20.58    20.66
 An integrated problem from the last 3 chapters: 21.60