Senior Instructor: Dr. Peter Marrs, Elliott 334c, 721-7172

Email: pmarrs@uvic.ca

Goals of the Course:

To practice known techniques and learn new techniques as applied to problems in the advanced organic laboratory. Most of the techniques will be familiar to you from the Chem 235/363 laboratory program. New techniques such as azeotropic drying, soxholet extraction, chiral reactions, and determination of mechanisms are introduced.

To understand the relationship between a compound's structure and the spectra (nmr,ir & esr) observed. Spectroscopic analysis (especially nmr) is paramount in determining the structure of small organic molecules. A variety of classes of organic compounds are synthesized in the laboratory, and the differences in their structure can be understood in terms of their spectra.

To understand the relationship between kinetic data/product structure and the mechanism of the reaction. Experiments in physical organic chemistry will establish a link between kinetics, structure and mechanism.

To gain self-confidence in a laboratory setting. The organic portion of Chemistry 463 is designed to act as a bridge between the typical undergraduate laboratory and the research laboratory. While the experimental procedures presented have been published, they are not as reliable as the (extensively) check procedures used in earlier courses.

The course takes place in Elliott 339. During the term, the organic laboratories are open Monday through Friday from 1:30 - 5:30 PM. The exact dates are determined in consultation with the other senior lab instructors, and will be announced later.

The Organic component of Chemistry 463 combines experiments from synthetic (S) and physical organic (P) chemistry. You are required to complete and report on three parts.

The first part is from the Investigations in Santonin Chemistry (listed under the Section A experiments), completing the tetrahydrosantonin and bromotetrahydrosantonin syntheses. The second and third parts may be completed by choosing between one of three possibilities: 

1) Finish the remaining two Santonin procedures, and do one experiment from section B. This makes for one longer report on Santonin, and a shorter "B" report for a total of two reports.

2) Choose a different section A experiment. This is now the longer report, and the Santonin report is shorter for a total of two reports.

3) Choose two Section B experiments. This gives two reports, plus a shorter one for Santonin and a total of three (but shorter) reports.

Make your choice (email me) and I'll get back to you. There are limits on the number of people who may do any one experiment.

Click on the title below to download a PDF copy of the experiment.

Section A:      Synthesis of Optically Active Atrolactic Acid (S)
                      Investigations in Santonin Chemistry (S)
                      Lignan Synthesis: Carpanone (S)
                      Kinetic Isotope Effects (P)
                      The Chemistry of Tetracyanoethylene (P)

Section B:      Asymmetric Synthesis Using Amino Acid Catalysis (S)
                      Spirocyclic Acetals (S)
                      Preparation and Spectra of an Organic Cation (S)
                      Facial Selectivity of a Hydrogenation Reaction (S)
                      Studies in Heterocyclic Synthesis (S)
                      Kinetic Isotope Effects (P)
                      The Chemistry of Tetracyanoethylene (P)
                      Catalysis: The Hydrolysis of Aspirin (P)
                      Determination of the Reactivity Ratios in a Copolymerization (P)

Manual - Download the experiments above.
References - The original journals, copies are available from me.
Safety Glasses - Must be purchased; available from Science Stores in Petch
Lab Coats - Recommended; available from Science Stores or Bookstore
Notebook - A notebook with fixed pages is mandatory. It need not be exclusive to this course.

Other Useful Downloads:          General Information
                                                Safety Precations in the Chemistry Laboratory
                                                Nmr Spectroscopy in the Undergraduate Laboratory

Each report will be graded out of 100, as will a technical evaluation. The final % is computed in one of two ways, depending on the number of reports submitted.

1) (Longer report x 0.55) + (shorter report x 0.35) + (technical evaluation x 0.10) = course %

2) (Each short report x 0.30) + (technical evaluation x 0.10) = course %

Click here for an approximate letter grade breakdown.

Due Dates:

The due dates for the terms have not yet been determined. They will not coincide with due dates from the other Chemistry 46X modules.

This page last updated July 5, 2011, by Peter Marrs.

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