CHEMISTRY 312

Intermediate Organic Chemistry II

The topics covered in CHEM 312 include an introduction to the chemical literature, the investigation of reaction mechanisms, industrial organic chemistry, photochemistry, and the chemistry of selected compounds of biological interest, e.g., steroids. Laboratory work will illustrate a selection of the topics covered during lectures and may involve a short research project.

CHEM 213 and CHEM 214.

The course will be based on the required text (Saferstein). Many case studies will be used to illustrate each topic, and the course will make use of reprint materials.

Introduction to the primary journals and review journals of Organic Chemistry (8 hours):

• Hands-on experience in the use of Chemical Abstracts (field-trip to SFU), computer searching (SFU assistance desirable), introduction to primary journals, to review journals and to other reference materials such as Beilstein, the Dictionary of Organic Compounds and Science Citation Index. 

• Using Chemical Abstracts - Peter Groves (Royal Society of Chemistry Audiotape), 1984;
• How To Find Chemical Information - Robert E. Maizeli (2nd edition) (John Wiley), 1987.

The Investigation of Organic Reactions (20 hours):

• Discussion of the various techniques used to investigate reaction mechanisms. Topics included: kinetics and equilibrium studies (6 hours), isotope effects (2 hours), structure-reactivity relationships (e.g. the Hammett equation) (6 hours), and stereochemistry (6 hours).

• Mechanism: An Introduction to the Study of Organic Reactions - Richard A. Jackson (Oxford University Press), 1972;
• The Investigation of Organic Reactions - Ross Stewart (Prentice-Hall), 1966;
• Physical Organic Chemistry Through Solved Problems - Joseph B. Lambert (Holden-Day), 1978;
• Mechanism in Organic Chemistry: Case Studies - R.O.C. Norman, M.J. Tomlinson & D.J. Waddington (Mills & Boon), 1978;
• Various original papers and reviews from J. Organic Chem., Chem. Reviews etc.

• Petrochemicals, dyes & dyeing, pharmaceuticals: emphasis on Canadian content.

• Survey of Industrial Chemistry - P.J. Chenier (Wiley-Interscience), 1986;
• The Second 50 Industrial Chemicals, Parts 1 & 2 - P.J. Chenier & D.S. Artibee (J. Chem. Ed. 65, 244-250, 433-436, 1988);
• The Teaching of Industrial Organic Chemistry - M.B. Hocking (Can. Chem. News 19-23, March 1991);
• Organic Chemistry - Norman L. Allinger et al (chapter 35) (Worth), 1971;
• Various articles and news items from C. & E. News, Chemistry & Industry etc.

• Molecular orbitals: basic theory, conjugated pi systems and pericyclic reactions; electrocyclic reactions; cycloadditions; Woodward-Hofmann rules, further u.v. visible spectroscopy.

Reference material:

• Organic Chemistry - 3rd edition - John McMurray (Brooks/Cole) ch 30, 1992;
• Organic Chemistry - Alan Wingrove & Robert L. Caret (Harper & Row) ch 27, 1981;

"Special Topics" (6 hours):

• Proteins (synthesis from amino acids, Merrified Automated method, protein analysis), enzymes, nucleic acids and nucleotides.

• Organic Chemistry - 3rd edition - John McMurray (Brooks/Cole) ch 29, 1992;
• Organic Chemistry - Alan Wingrove & Robert L. Caret (Harper & Row) ch 28, 1981;