Course Syllabus
Lecture
Topic
Reading
Sept. 3
Scope of organic chemistry
5
The classical structural model
Chap. 1.1-1.2, 1.9
8
The orbital model
Chap. 1.3-1.4, 1.6-1.7
10
The hybridization model
Chap. 1.8
12
Isoelectronic analogies; resonance
Chap. 1.5
15
Acids & bases; functional groups
Chap. 2.2-2.5
17
Conformational analysis
Chap. 2.6-2.8
19
Conformations of rings, ring strain
Chap. 4.1-4.2
22
Cyclohexane conformations
Chap. 4.3-4.7
24
Thermodynamics and kinetics
Chap. 2.1
26
Thermokinetic principles; Observations on alkane halogenation
29
Chlorination of alkanes; selectivity
Chap. 3.1-3.4
Oct. 1
Structure of free radicals; Review
Chap. 3.5-3.8, 3.10
2
Prelim 1
3
Resonance model
Chap. 14.1-14.2; 22.1
8
Chirality
Chap. 5.1-5.4
10
Symmetry
Chap. 5.5-5.6
13
Further symmetry considerations
Chap. 5.7-5.8
15
Cycloalkane conformations and chirality
17
Nucleophilic substitutions (SN2)
Chap. 6.1-6.6
20
Nucleophilic substitutions (SN2)
Chap. 6.7-6.9
22
SN1 nucleophilic substitutions
Chap. 7.1-7.5
24
SN1 nucleophilic substitutions
27
E2 eliminations
Chap. 7.6-7.9
29
Alcohols: properties & synthesis
Chap. 8.1-8.5
31
Oxidation; Grignard reagents;
Chap. 8.6-8.8
Nov. 3
Synthesis
Chap. 8.9
5
Substitution reactions with alcohols; carbocation rearrangements
Chap. 9.1-9.3
6
Prelim 2
7
Ether synthesis and reactions
Chap. 9.4-9.8
10
Oxacyclopropanes (Epoxides)
Chap. 9.9-9.10
12
Alkenes: Addition of H-X
Chap. 11.1-11.3, 11.9-11.11
Chap. 12.1, 12.3-12.4
14
Bromination and Related Additions
Chap. 12.5-12.6
17
Oxymercuration and Hydroboration
Chap. 12.7-12.8
19
Cyclopropanation and Epoxidation
Chap. 12.9-12.10
21
Hydrogenation, KMnO4, OsO4, Ozonolysis
Chap. 12.2, 12.11-12.12
24
The HBr Problem
Chap. 12.13
26
Special Topics
Dec. 1
Synthesis
3
Review
4
Prelim 3
5
Electrophilic additions to alkynes
Chap. 13.1-13.3, 13.7-13.8
8
Alkynes: synthesis
Chap. 13.4-13.6
10
Review
15
Final Exam