“everybody wins” - improving the undergraduate organic laboratory experience via student...
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“Everybody Wins” - Improving The
Undergraduate Organic Laboratory
Experience Via Student Research Projects
Dr. Andy Dicks Undergraduate Chair
Department of Chemistry
University of Toronto
Chemistry Undergraduate Research 2007-08
CHM 299Y - 20 faculty offer projects - a record 55 students enrolled
Funded summer research positions (29) for 2nd/3rd year students - three of these in Germany
CHM 4XXY - five full-year research courses in chemical sub-disciplines (24 students) (e.g. CHM 449Y = organic chemistry)
Laboratory Curriculum Renewal
CHM 346H (Modern Organic Synthesis): enrollment 35
CHM 348H (Organic Reaction Mechanisms): enrollment 65
Involve CHM 299Y, summer and CHM 449Y students in designing new experiments
for these courses
“Hooks” For New Experiments In CHM 346H
Synthesis of “real-world relevant” organic compounds
“Green chemistry”: (i) microscale reactions; (ii) replacing organic solvents with water; or (iii) performing reactions “solvent-free”
“Discovery-based” experiments that involve problem-solving and student input
Example 1: Sunscreen Analog Synthesis (1)
Active ingredient:octyl 4-methoxycinnamate:
Ryan Stabile (CHM 449Y, 2001)
~50%
(E)-4-methoxycinnamic acid
C
O
H
O
β-alanine, pyridine, Δ
O
COOH
+COOH
COOH
1)
2) H3O+
O
O
O
Cs2CO3, DMFC2H5I
ethyl (E)-4-methoxycinnamate
O
O
O
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
Example 2: “Keeping Your Students Awake”
Modafinil:
marketed as Provigil byCephalon in theUnited States
June Lin (summer research 2004)
Prescription anti-narcoleptic with limited abuse potential
~55%
SNH2
O
H2O2, CH3COOH
50 C, 90 min.0
SNH2
OO+
-
(±)-modafinil (Provigil)synthesized "in-house"
CHM 299Y Program, 2005/06
Title: “Developing A Chemical Education Laboratory (ChemEdLab)”
Six students enrolled (39 applied)
Six laboratory hours/week for 24 weeks
Teaching assistant and lecturer supervision
CHM 299Y: Aqueous NSAID Analog Synthesis
ROP 299Y students, Fall 2005
Active ingredient:
Suzuki reaction in water
Elimination of organic solvents/bases to forman anti-inflammatoryanalog
~75%
OH10% Pd/C, aq. K2CO3
B(OH)2
+
OH
I30 minutes
O H
C O O HF
F
CHM 299Y: Problem-Solving In CHM 346H
ROP 299Y students, Fall 2005
Moving away from “recipe-driven” experiments
Students individually plan, check for safety and execute synthesis of Alzheimer’s disease drug candidates
Azlactones
H2N
O
OH ???
glycine (3.0 g)O
N
O
W
X
Y
Z
CHM 299Y Student Evaluation
Two detailed written reports (end of Fall and Spring semesters)
Participation in Undergraduate Research Fair (three posters)
Development of practical skills
Attendance at Southern Ontario Universities Student Chemistry Conference (March 2006)
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”
Summary - Why Does “Everybody Win”?
Thirteen students have designed 16 new experiments
for 300-level organic chemistry laboratories since 2001
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)