Download 19 Amines and Amides Study Goals

Chapter 19
19
Amines and Amides
Study Goals
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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