CHEMISTRY 311

Intermediate Organic Chemistry I

An intermediate level Organic Chemistry course involving a detailed study of condensation reactions, dienes and heterocyclic compounds. The approach will be by reaction mechanism and synthesis. The spectroscopic techniques first introduced in Chem 214 are examined in more detail, both in theory and in practice. The laboratory component of the course involves the synthesis of a variety of compounds and qualitative analysis by both spectroscopic and chemical means.

Chemistry 213 and 214

Mass spectroscopy (6 hours):

• Mass spectroscopy - general methodology. Identification of fragment ions and radical fragments in the fragmentation of alkanes, alcohols, alkenes and alkyl halides.

• Review of proton magnetic spectroscopy, more complex splitting patterns; calculation of J coupling constants, long-range coupling; 13C n.m.r. spectroscopy; n.m.r. spectra of larger molecules.

Conjugated Dienes and Ultra-violet Spectroscopy (8 hours):

• Preparation and stability of conjugated dienes; molecular orbital description of 1,3-butadiene; electrophilic addition (1,2 & 1,4 addition); Diels-Alder cycloaddition reactions; other conjugated systems. Ultra-violet spectrum of 1,3-butadiene. Ultra-violet spectroscopy of other conjugated systems. Woodward-Hofmann and Woodward-Fieser rules.

• Review of aldol condensation reactions (from 212); Claisen condensation reaction, Dieckmann reaction; Michael reaction, Perkin reaction, Stork enamine reaction, carbonyl condensation reactions in syntheses, Wittig reaction, Robinson annulation; and in biological systems.

• Structures of five membered rings: pyrrole, furan, thiophene; electrophilic substitution. Structures of six-membered rings: pyridine - electrophilic and nucleophilic substitution. Fused heterocycles.