CHEM 442 - Advanced Organic Chemistry

(3 units)

Organic reactions not generally covered in introductory courses in organic chemistry. Emphasis on both synthetic utility and reaction mechanisms.

Prerequisite(s): CHEM 342 or CHEM 443; CHEM 422.

Grading Basis: Graded
Units of Lecture: 3
Offered: Every Fall

Student Learning Outcomes
Upon completion of this course, students will be able to:
1. identify and compare steric, electronic, and stereoelectronic effects.
2. analyze the stereochemistry of molecules and assign correct configurations.
3. evaluate and explain carbocation stability and reactivity in classic and non-classical cationic systems.
4. contrast thermodynamic and kinetic control in reactions, and explain and apply primary and secondary kinetic isotope effects, transition-state theory, Curtin-Hammett principle, Hammett plots, and the Hammond postulate.
5. evaluate addition and elimination reactions and predict and explain reaction outcomes by drawing clear “arrow-pushing” mechanisms along with the regio-, stereo-, and chemoselectivity of these reactions.
6. evaluate and explain substitution and thermal isomerization reactions by drawing clear arrow-pushing mechanisms and the regio-, stereo-, and chemoselectivity in these reactions.
7. evaluate and explain pericyclic reactions (cycloadditions, electrocyclizations, and sigmatropic rearrangements) and propose their mechanisms, using the concepts of aromaticity and Frontier Molecular Orbital (FMO) theory.

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