1. Carboxylic acids and Their Derivatives By Prof. Dr. Adel M. Awadallah
Organic chemistry for medicine and biology students
Chem 2311
Chapter 19 & 20
Carboxylic acids and Their Derivatives
By Prof. Dr.
Adel M. Awadallah
Islamic University of Gaza

10. Diacids

12. Physical Properties of carboxylic acids
Hydrogen bonding
Solubility in water
(lower acids)

14. Acidity of carboxylic acids
pKa = -log Ka
As Ka increase or pKa decrease, the acidity increase

16. Resonance and Inductive effect
Conversion of acids to salts

18. Preparation of carboxylic acids

20. Acids, hydroxy acids, amino acids, and unsaturated acids from cyanohydrines

21. Reactions of carboxylic acids

22. Hell-Volhard-Zelinsky Reaction
                                                                                                  
Treatment with bromine and a catalytic amount of phosphorus leads to the selective α-bromination of carboxylic acids.

23. Mechanism of the Hell-Volhard-Zelinsky Reaction Phosphorus reacts with bromine to give phosphorus tribromide, and in the first step this converts the carboxylic acid into an acyl bromide.

26. Esters
Nomenclature

28. Examples

32. Lactones (Cyclic Esters)

37. Reactions of Esters with Grignard Reagent

38. Formation of Amides (Ammonolysis of Esters)

39. Reduction of Esters
Esters can be reduced to primary alcohols

40. The Cliasen Condensation

41. Acid Halides
They are prepared from the reaction of acids with thionyl chloride or phosphorus halides

44. Reactions of acid chlorides
Acid chlorides react rapidly with most nucleophiles such as water, alcohols and ammonia
Acyl halides have irritating odors. Benzoyl chlorid is a lachrymator
(tear gas)

45. Reaction with Grignard Reagent

48. Preparation of mixed anhydrides

49. Mixed anhydrides

50. Nucleophilic substitution of anhydrides

51. Amides
Nomenclature

52. Properties of Amides

54. Amide Resonance

58. Reactions of Amides (Hydrolysis and Reduction)