The Ohio State University, Chemistry Department Autumn 2012




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The Ohio State University, Chemistry Department Autumn 2012

Tentative Syllabus for




Chem 6420: “Stereochemistry and Conformational Analysis”


Stereoisomerism (1 lecture) – enantiomers & origin of chirality, diastereomers, absolute configuration (R/S, M/P, D/L), relative configuration.


Resolution of Enantiomers (2 lectures) – crystallization, separation via diastereomeric derivatives, measurement of enantiomeric purity, kinetic resolution, enzymatic resolution.


Conformational Analysis (6 lectures) – ethane, Pitzer (torsional) strain, propane, butane, gauche interactions, pentane and syn-pentane interaction, conformations of CH3–X–Hn (X = O, N), alkenes and carbonyl compounds, conjugated systems, esters/amides, ring strain, cyclohexane (A-values, calculation of Keq from G°), cyclohexene systems, allylic strain, decalins.


Stereochemistry of Dynamic Processes (6 lectures) – prostereoisomerism, homotopic vs. heterotopic ligands and faces, Curtin-Hammett principle and reactions of equilibrating systems, Hammond postulate and kinetic vs. thermodynamic control, stereoselective vs. stereospecific, cyclization reactions, Thorpe-Ingold effect, Baldwin’s rules, conformation and reactivity in cyclohexane systems.


Stereoelectronic Effects (6 lectures) – SN2, SN2´, E2 reactions, additions to cyclohexenes, Fürst-Plattner rule, additions to carbonyl groups (Felkin-Anh and Cram models), facial selectivity in cyclohexanones, anomeric and exo-anomeric effect in glycosides, 1,4-eliminations and ring expansions, halohydrin rearrangements, reactions at benzylic carbons, acetals and esters


Chemistry 6420: Stereochemistry and Conformational Analysis (AU 2012)

1. Texts and Study Aids

1. Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry, 5th Ed. Parts A and B, Kluver Academic: New York, 2007. Also useful for Chem 6410, 6430, and 7430.

2. Carruthers, W.; Coldham, I. Modern Methods of Organic Synthesis, 4th Ed.; Cambridge University Press: Cambridge, 2004.

3. Anslyn, E. V.; Dougherty, D. A. Modern Physical Organic Chemistry University Science Books: Suasalito, 2006. Also useful for Chem 6410, 6430, and 7430.

4. Wyatt and Warren: Organic Synthesis, Strategy and Control, Wiley: Chichester (2007) (web: cs-books@wiley.co.uk) ISBN 978-0-471-92963-5 (paperback)

5. Ian Fleming: Molecular Orbitals in Organic Chemical Reactions, Wiley: Chichester (2009) (web: cs-books@wiley.co.uk) ISBN 978-0-470-74659-2 (paperback)


Good set of molecular models.

2) Brief description of the course




Fundamental principles of stereochemistry, including stereoisomerism, enantiomer resolution,

conformational analysis of C-C and C-heteroatom bonds, cyclic stereochemistry,

the stereochemistry of dynamic processes, and stereoelectronic effects.
Prereq: 2520 (253), 2620 (253), 2920H, or equiv. Not open to students with credit for 730.










3) A brief list (1 to 10 items) of the main topics that will be covered in the course


Stereoisomerism– enantiomers & origin of chirality, diastereomers, absolute configuration (R/S, M/P, D/L), relative configuration.

Resolution of Enantiomers –crystallization, separation via diastereomeric derivatives, measurement of enantiomeric purity, kinetic resolution, enzymatic resolution.

Conformational Analysis – ethane, Pitzer (torsional) strain, propane, butane, gauche interactions, pentane and syn-pentane interaction, conformations of CH3–X–Hn (X = O, N), alkenes and carbonyl compounds, conjugated systems, esters/amides, ring strain, cyclohexane (A-values, calculation of Keq from G°), cyclohexene systems, allylic strain, decalins.

Stereochemistry of Dynamic Processes – prostereoisomerism, homotopic vs. heterotopic ligands and faces, Curtin-Hammett principle and reactions of equilibrating systems, Hammond postulate and kinetic vs. thermodynamic control, stereoselective vs. stereospecific, cyclization reactions, Thorpe-Ingold effect, Baldwin’s rules, conformation and reactivity in cyclohexane systems.

Stereoelectronic Effects – SN2, SN2´, E2 reactions, additions to cyclohexenes, Fürst-Plattner rule, additions to carbonyl groups (Felkin-Anh and Cram models), facial selectivity in cyclohexanones, anomeric and exo-anomeric effect in glycosides, 1,4-eliminations and ring expansions, halohydrin rearrangements, reactions at benzylic carbons, acetals and esters

References


1. Fuhrhop, J. and Li, G; Organic Synthesis; 3rd Edition, Verlag Chemie: Weinheim, 2003.

2. Warren, S. Organic Synthesis: The Disconnections Approach, Wiley: New York.

3. Warren, S. Workbook for Organic Synthesis: The Disconnections Approach, Wiley: New York.

4. March, J. Advanced Organic Chemistry, 4th Ed.; Wiley: New York, 1992. QD251.2.M3

5. House, H. O. Modern Synthetic Reactions, 2nd Ed.; Benjamin: New York, 1972. QD262.H67

6. Deslongchamps, Pierre; Stereoelectronic Effects in Organic Chemistry; Pergamon; New York, 1983. QD481.D47

7. Eliel, E.; Wilen, S. H. “Stereochemistry of Organic Compounds” Wiley: New York, 1994, QD481.E42

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