You are expected to be familiar with the material described
in chapters 15, 16 & 22 (Benzene, Aromaticity, Core and Sidechain
in chapters 17, 19 & 20 (AK, Acids and Derivatives),
in chapters 18 and 23 (enolates),
and in chapter 21 (amines).
Topics on carbohydrates (chapter 24) also will be included in as much as
they were covered in the lecture and with focus on structure.
Heterocycles (chapter 25) and amino acids (chapter 26) will not be
included. Aside from the material covered in the
lecture, you should also be familiar with the associated problem assignments
and GTQ worksheets. Textbook material that was omitted in
lecture will not be pertinent to the test. Futhermore, the test will not
require any details on mass spectrocopy and only the very
basics of NMR and UV/Vis spectroscopy.
Specific Important Topics
This list is now (as of 11/23/96) more or less "complete"
although it is not meant to be exclusive.
From chapters 15, 16 & 22 (Benzene and Derivatives):
Electrophilic aromatic substitution. (Will test for
Nucleophilic aromatic substitution. (Will test for
Know mechanisms and orientation effects for both kinds of reactions.
From chapters 17, 19 & 20 (A/Ks & Acids):
Oxidations and reductions.
Reactions with nucleophiles.
Wittig Reaction. (Will test for sure)
From chapters 18 and 23:
Halogenation and Alkyation of A/Ks.
Aldol reaction and its variations.
1,2- and 1,4-additions to alpha,beta-unsaturated carbonyls.
Claisen condensation and its variations including Dieckmann
Acetoacetic acid synthesis & malonic ester synthesis
From chapter 21:
Alkylation of amines.
Syntheses of primary, secondary, and tertiary amines.
Hofmann elimination. (Will test for sure)
Will not test the Mannich reaction.
Nitrosation of amines.
Carbenes: Preparation and Reactions. (Will test for
From chapter 24:
Structure of acyclic and cyclic sugars (incl. Fischer & Haworth).
Anomers and Mutarotation.
(Will test for sure)
Di- and polymerization of sugars.