SCH 411 Organic Stereochemistry
January 2017 – April 2017
Course Director: Dr. Charles O Ochieng
Course Description:
Molecular geometry and chemical bonding involving organic compounds; molecular models and
planar depictions of compounds; conformational analysis and stereoisomerism in saturated and
cyclic compounds; concepts and applications of chirality and molecular symmetry in
physiological processes and synthetic organic chemistry
Course Objectives:
Upon completion of this course, the student should be able to:
1. Understand the basic of stereochemistry, physical properties of isomers, synthesis and
reactions and Applications of the organic stereochemistry.
2. Gain the knowledge of Stereoisomers, Conformational Isomerism, Ethane
Conformations, Butane Conformations, Structural Equivalence and Non-equivalence of
Groups, Structural Classification of Atoms or Groups,
3. Understand the stereochemical indications for SN1, SN2, E1, E2.
4. Predict possible stereochemical path way of problems and the products.
Recommended Textbooks:
1. "Stereochemistry of Organic Compounds" by Eliel and Wilen, Wiley, 1994
2. "Intermediate Organic Chemistry" (2nd edition) by Stowell, Wiley, 1994
3. "Organic Chemistry, An Intermediate Text" by Hoffman, Oxford, 1997 (preferred
Intermediate text)
4. "Advanced Organic Chemistry" (4th edition) by March, Wiley, 1992
5. "Advanced Organic Chemistry" Parts A&B (3rd edition), by Carey and Sundberg,
Plenum, 1990
6. "Reagents for Organic Synthesis" by Fieser and Fieser (17 volumes and counting)
7. "Comprehensive Organic Synthesis," (9 volumes) many authors (Pergamon Press)
NOTE
i) Every student is required to purchase the recommended textbooks.
ii) Lectures will be given from these books; students are required to read the assigned
chapters for every lecture. The lecture may not cover everything. Examinations will be
from the lectures and respective chapters in the textbooks.
Attendance:
1
Students MUST attend all lectures and exercises, and be ON TIME. Student who fails to attend
a lecture must report to the COURSE LECTURER or COD the reason behind his/her absence.
Any student who fails to attend 75% of the lectures, will not be allowed to sit for the FINAL
EXAMINATION. No excuse whatsoever.
Grading:
EXAME WEEK Marks
1 Midterm exam I 7 10%
2 Midterm exam II 12 10%
3 Quizzes every 5%
week
4 Homework and projects. 5%
5 Final exam 14 70%
Students MUST pass all parts and must achieve 40 % out of 100 to pass the course.
Lecture Outline
January 2017 – April 2017
Week Date Topic Remarks
1 Introduction and course requirements
Introduction to Stereochemistry
stereochemical nomenclature & terminology
1. Discussion of chirality (chiral carbons, allenes,
2 17/1/2018
biphenyls, etc.)
2. nomenclature (R/S, E/Z, D/L, d/l)
3. 2-D representations (line drawings, Fischer
projections, Haworth projections)
Stereoisomers, Conformational Isomerism,
1. Ethane Conformations,
2. Butane Conformations,
3 24/1/18
3. Structural Equivalence and Non-equivalence of
Groups, Structural Classification of Atoms or
Groups,
4 31/1/18 Configurational Stereoisomers of Cycloalkanes,
1. Ring Conformers,
2. Some Conformations of Cyclohexane Rings,
2
3. Substituted Cyclohexane Compounds,
4. bicyclic compounds
Configurational Stereoisomers of Alkene,
1. The Sequence Rule for Assignment of Alkene
5 7/2/218 Configurations,
2. Relationship of Constitutional and
Stereoisomers,
Chirality and Symmetry,
1. Symmetry in Organic Chemistry,
2. Stereogenic Elements and Stereoisomerism,
Stereogenic Elements and Stereoisomerism,
6 14/2/2018 R,S conformer (L, D of carbohydrats)
3. stereochemical terminology for sugars, amino
acids
Identifying stereochemical relationships
1. enantiomers, diastereomers, epimers, Meso
7 21/2/2018
Diastereomers etc.)
2. Racemization, Formation of racemic mixtures
Stereochemical analysis: determination of relative and
absolute configuration
1. polarimetry (optical activity, specific rotation,
ee)
2. Chiral resolution, by crystallization, Chiral
8, 9 28/2/2018 resolving agents
3. chiral GC HPLC, & Chiral column
chromatography
4. NMR techniques
5. physical and chemical properties of
stereoisomers
10 7/3/2018 1st MID-TERM EXAMINATION
Stereochemistry of organic reactions
1. prochiral environments (enantiotopic,
diastereotopic)
11 14/3/2018 2. SN2 (inversion)
3. reactions which proceed with racemation
3
Elimination mechanisms (E2, Hoffmann)
12 21/3/2018
1. Additions to alkenes (syn, anti, Diels-Alder):
2. Addition to Carbon-Carbon Double Bonds,
Hydroboration, Epoxidation,
3. Addition to Carbonyl Double Bonds (Cram's
rule)
13
4. Stereoselective Synthesis, Models for Addition
to Acyclic Substrates, The Chelation Effect,
Non-chelating Polar Effects,
Diastereoselectivity, Enantioselectivity,
Chiral techniques and syntheses
1. optical resolution
14 28/3/2018 2. asymmetric oxidations & reductions
3. asymmetric C—C bond forming reactions
4. use of catalytic enzymes
15 4/4/12018 2ed CAT
16 Examination
