Chapter 19: Carboxylic Acids Learning Goals

  1. You can provide a proper, unique name for a carboxylic acid, given its structure.
  2. You can draw a correct structure for a carboxylic acid, given its name.
  3. You recognize the function of a carboxylic acid as a Briønsted acid, and its ability to form hydrogen-bonded dimers.
  4. You know the IR stretch for the C=O double bond, and the special behavior of the O-H band. You know how the carbonyl group affects proton and 13C chemical shifts in the NMR spectrum, and where carbonyl carbons in carboxylic acids appear in the 13C spectrum.
  5. You remember how to oxidize primary alcohols to carboxylic acids. (Chapter 8, 17)
  6. You know how to make carboxylic acids by carboxylation of Grignard reagents.
  7. You know how to make carboxylic acids by hydrolysis of amides, nitriles, esters and acid chlorides.
  8. You remember how to make carboxylic acids by ozonolysis of alkenes, and the structural requirement for this reaction. (Chapter 12)
  9. You remember how to oxidize aldehydes to carboxylic acids. (Chapter 17)
  10. You recognize that reaction of a Brønsted base with a carboxylic acid will result in formation of a salt. You recognize the role this plays in the difficulty of making amides from carboxylic acids and amines.
  11. You know how to reduce a carboxylic acid to a primary alcohol.
  12. You know how to make an ester from a carboxylic acid via Fischer esterification.
  13. You know how acid chlorides are prepared using thionyl chloride.
  14. You know how diazomethane is used to make methyl esters.
  15. You know how to reduce carboxylic acids to either primary acohols or to aldehydes via the acid chloride.
  16. You know why addition of alkyllithium reagents to carboxylic acids can create ketones.
Friday fun: Soap, micelles and the lipid bilayer
Recommended problems: 
19.27    19.30    19.32    19.33    19.36    19.37
    19.39    19.45    19.52    19.54 (ignore identification of M)