1. “Everybody Wins” - Improving The Undergraduate Organic Laboratory Experience Via Student Research Projects Dr. Andy Dicks Undergraduate Chair Department of Chemistry University of Toronto

2. Chemistry Undergraduate Research 2007-08 l CHM 299Y - 20 faculty offer projects - a record 55 students enrolled l Funded summer research positions (29) for 2 nd /3 rd year students - three of these in Germany l CHM 4XXY - five full-year research courses in chemical sub-disciplines (24 students) (e.g. CHM 449Y = organic chemistry)

3. Laboratory Curriculum Renewal l CHM 346H (Modern Organic Synthesis): enrollment  35 l CHM 348H (Organic Reaction Mechanisms): enrollment  65 Involve CHM 299Y, summer and CHM 449Y students in designing new experiments for these courses

4. “Hooks” For New Experiments In CHM 346H l Synthesis of “real-world relevant” organic compounds l “Green chemistry”: (i) microscale reactions; (ii) replacing organic solvents with water; or (iii) performing reactions “solvent-free” l “Discovery-based” experiments that involve problem-solving and student input

5. Example 1: Sunscreen Analog Synthesis (1) Active ingredient: octyl 4-methoxycinnamate: Ryan Stabile (CHM 449Y, 2001)

6. Sunscreen Analog Synthesis (2) Ryan Stabile (CHM 449Y, 2001) Stabile, R. G.; Dicks, A. P. J. Chem. Educ., 2004, 81, 1488-1491 Sunscreens highlighted as “Featured Molecules” in Journal of Chemical Education October 2004

7. Example 2: “Keeping Your Students Awake” Modafinil: marketed as Provigil by Cephalon in the United States June Lin (summer research 2004) Prescription anti-narcoleptic with limited abuse potential

8. CHM 299Y Program, 2005/06 l Title: “Developing A Chemical Education Laboratory (ChemEdLab)” l Six students enrolled (39 applied) l Six laboratory hours/week for 24 weeks l Teaching assistant and lecturer supervision

9. CHM 299Y: Aqueous NSAID Analog Synthesis ROP 299Y students, Fall 2005 Active ingredient: Suzuki reaction in water Elimination of organic solvents/bases to form an anti-inflammatory analog

10. CHM 299Y: Problem-Solving In CHM 346H ROP 299Y students, Fall 2005 l Moving away from “recipe-driven” experiments l Students individually plan, check for safety and execute synthesis of Alzheimer’s disease drug candidates Azlactones

11. CHM 299Y Student Evaluation l Two detailed written reports (end of Fall and Spring semesters) l Participation in Undergraduate Research Fair (three posters) l Development of practical skills l Attendance at Southern Ontario Universities Student Chemistry Conference (March 2006)

12. SOUSCC 2006, York University Leo Mui (far left) wins the Chemical Education Division Undergraduate Chemistry Award ““Green” Syntheses of Aromatic Compounds via Aqueous Heck and Suzuki Reactions for the Undergraduate Laboratory”

13. Summary - Why Does “Everybody Win”? Thirteen students have designed 16 new experiments for 300-level organic chemistry laboratories since 2001

14. Acknowledgements CHM 449Y: Summer Research: Ryan Stabile (2001) Karen Jang (2002) Jason McIntee (2002) June Lin (2004) Vangelis Aktoudianakis (2003) Laura Minea (2006) Lawrence Cheung (2004) ROP 299Y 2005/06: $$$: Elton Chan Xerox (J. Lin) Amanda Edward Isabel Jarosz Chemistry Lecturer Vicki Lee Scholar Fund (CHM 299Y) Leo Mui Sonya Thatipamala A&S Instructional Initiative Grant (CHM 449Y)