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Chapter 19 19 Amines and Amides Study Goals • • • • • • Name and write structural formulas of amines and amides. Describe the ionization of amines in water. Describe the boiling points of amines and amides compared to alkanes and alcohols. Describe the solubility of amines and amides in water. Write equations for the neutralization and amidation of amines. Describe acid and base hydrolysis of amides. Chapter Outline 19.1 19.2 19.3 19.4 19.5 19.6 19.7 Amines Health Note: Amines in Health and Medicine Naming Amines Physical Properties of Amines Amines React as Bases Heterocycli Amines and Alkaloids Health Note: Synthesizing Drugs Structure and Names of Amides Health Note: Amides in Health and Medicine Hydrolysis of Amides Chapter Summary and Demonstrations 1. Amines and amides The final chapter on organic chemistry discusses nitrogen-containing compounds along with their amide derivatives. Amines are classified as primary, secondary and tertiary and named according to IUPAC and common naming systems. Heterocyclic amines are introduced and their role in alkaloids and other physiological amines is described. Demonstration: Amines and Amides Amines and amides are introduced by a discussion of commonly occurring nitrogen-containing compounds such as fish, window-cleaners, and certain drugs. At this time, I hand out pharmacy leaflets that come with prescription drugs. Students identify the functional groups as well as the amine and amide bonds that give physiological activity. As extra credit, they can write a paper about the drug, its functions, and side effects. Amines and Amides Laboratory Suggestions Lab 33 Amines and Amides Amines are classified as primary, secondary or tertiary, their structural formulas drawn, and their names written. Some physical properties of amines are observed and an equation is written for the formation of amine salt, amidation and hydrolysis reactions. A. Structure and Classification of Amines B. Solubility of Amines in Water C. Neutralization of Amines with Acids D. Amides Laboratory Skills to Demonstrate Proper technique in noting the odor of a compound. Care in the use of concentrated ammonia. Caution in the use of conc. H3PO4 Proper use of the Büchner funnel and filtration apparatus Lab 34 Synthesis of Acetaminophen The analgesic acetaminophen is synthesized from p-aminophenol and acetic anhydride. The product may be purified and the percent yield calculated. Acetanilide is isolated from an impure sample and the percent yield is determined. A. Synthesis of Acetaminophen B. Isolating Acetanilide from an Impure Sample Laboratory Skills to Demonstrate Care in working with p-aminophenol and acetic anhydride. Proper use of the Büchner funnel and filtration apparatus Lab 35 Plastics and Polymerization Synthetic polymers found in common household products are sorted using density, combustion, and solubility in acetone. Gluep and Slime® are from polyvinyl alcohol or Elmer’s glue and a saturated borax (NaB4O7) solution. Polystyrene is synthesized from styrene monomers as an example of plastics used to make plastic glasses and coffee cups. Nylon, which is a group polyamides made by the condensation of diamines and dicarboxylic acids, is synthesized and pulled from an interface as a thread. A. Classification of Plastics B. Gluep and Slime C. Polystyrene D. Nylon Laboratory Skills to Demonstrate Formation of aluminum boat for polystyrene Care in the use of hexamethylenediamine and sebacic chloride and respiratory Process of forming an interface and removal of nylon polymers