1. Transition to an Investigative Laboratory Program in Chemistry at Birmingham-Southern College David J. A. Schedler and Laura K. Stultz

2. Introduction National Science Foundation Grant Investigative Laboratories Development of Laboratory Projects Examples

3. Project Goals Student Goals Improve - Problem solving and collaborative skills - Ability to apply experimental techniques to solve a chemical problem. - Ability to communicate results (written and oral) Curricular Goals - Improved laboratory experience - Better synergy between lecture and laboratory - Connections between chemistry courses

4. Investigative Laboratories Students discover results instead of verifying them Experimental protocols are largely student designed Work is done in collaborative groups Interpretation of results through data analysis Group discussion

5. Project Plan Gradualism Model – stepwise presentation of new material with specific goals Instrumental techniques as common thread - Molecular Modeling - FTNMR ( 1 H and 13 C) Project based Laboratories – Reinforces concepts and skills Student involvement in laboratory design

6. First Semester Focuses on Techniques and Instrumentation Distillation Crystallization Melting point TLC GC NMR

7. Second Semester Focuses on Application NMR FT-IR Molecular modeling Stereochemistry and Coupling Constants

8. Projects should have clearly stated: Objective Outcome Introduction Theory for the instrumentation to be used background into the chemistry involved Experimental Procedure

9. 1.34 kcal/mol2.39 kcal/mol

10. EntryDihedralExpected Dihedral Angle (°) Expected value (Hz) 1H ax CCH e q 602.5 2H ax CCH e q 602.5 3H ax CCH a x 18012 4H ax CCH a x 18012 EntryDihedralExpected Dihedral Angle(°) Expected value (Hz) 1H eq CCH eq 602.5 2H eq CCH eq 602.5 3H eq CCH ax 602.5 4H eq CCH ax 602.5

12. Ψ Quintet Ψ Triplet of Ψ triplets

13. Diels-Alder Reaction prediction of reaction product carry out reaction using previously learned lab techniques Adapted from: McDaniel, Keith F.; Weekley, R. Matthew “The Diels-Alder Reaction of 2,4-Hexadien-1-ol with Maleic Anhydride: A Novel Preparation for the Undergraduate Organic Chemistry Laboratory Course” J. Chem. Educ. 1997, 74, 1465.

14. Structure Determination NMR IR Mechanistic explanation

15. DihedralMeasured Angle A (°) Calculated J Value A (Hz) Measured Angle B (°) Calculated J Value B (Hz) H 1 CCH 2 18.938.42179.31 11.19 H 2 CCH 3 40.365.6153.33 3.64 H 3 CCH 4 45.284.8599.05 1.18 www.casper.organ.su.se/ke3690/jhh.html program calculates 3JHH values according to: C.A.G. Haasnoot, F.A.A.M. DeLeeuw and C. Altona Tetrahedron 36 (1980) 2783-2792

17. H2H2 H3H3 H1H1 DihedralMeasured Angle (°) Calculated J Value A (Hz) Measure J Value A (Hz) H 1 CCH 2 18.938.428.9 H 2 CCH 3 40.365.615.5 H 3 CCH 4 45.284.854.6

18. Electron Transfer Self Exchange Rates Kinetic NMR experiment Factors that affect the electron transfer rates Jameson, D.L.; Anand, R. J. Chem. Ed., 2000, 77, 88

19. Acknowledgements National Science Foundation (Award DUE-0126478) Dr. Regina Stanton Mr. Patrick McTamney Ms. Karen Johnson Mr. Nathan Boyd Birmingham-Southern College www.bsc.edu/chemistrylabs.htm