1. Introducing GC/MS into the Undergraduate Organic Lab
Dan Blanchard, Ph.D.
Kutztown University

2. GC/MS as an Organic Tool
Goals of Organic Lab
Characterization
Logistics
Challenges
Experiments
Conclusions

3. Goals of Organic Laboratory at KU
Learn Laboratory Techniques
Carry Out Organic Syntheses
Explore Chemistry of Everyday Life
Demonstrate Concepts from Lecture
Most Involve Synthesis or Isolation

4. Importance of Characterization
Synthesis Routine
React
Isolate
Purify
CHARACTERIZE
Isolation Routine
Isolate
Purify
CHARACTERIZE

5. Characterization Traditionally Melting Range GC/MS
Not related to structure
Sample purity dependence
Not modern techniqe
GC/MS
Can be introduced early at basic level
Can be developed across the course
Modern technique

6. GC/MS – Logistics
Should students operate the instrument in the Organic lab?
One Solution: The Autosampler
Allows for more samples and longer run times
Students can enter their own information.
Students should get to operate the instrument once.

7. Challenges of Introducing GC/MS
Introducing two techniques at once
Two graphs for one run!
Heaviest ion versus most abundant ion
Fragmentation: multiple simultaneous reactions

8. Identification of Volatile Flavor Components by Headspace Analysis
Simple sample preparation
Short run times
Identification is made by molar mass alone
limonene, ethyl butyrate, benzaldehyde, isoamyl acetate
Drawback: Not all candies have adequate volatile components
Kjonaas, R.A.; Soller, J.L.; McCoy L.A., J. Chem. Educ. 1997, 74,

9. Isolation of the Active Ingredients from Cough Syrup
Includes acid-base extraction
Example of combining traditional concept with GC/MS
Sherren, A. T. Presented at The American Chemical Society National Meeting, Boston, MA, 1999.

10. Fatty Acids Present in Snack Foods
Isolation of oils from potato chips
Detection of prepared FAMES
No MS interpretation
Food for discussion
Rubinson, J.F.; Neyer-Hilvert, J., J. Chem. Educ. 1997, 74,

11. Grignard Synthesis of an Unknown C6-C9 Alcohol
Unknown alkyl halide plus unknown ketone
Product is characterized by IR, 13C NMR, GC/MS
NO molecular ion
Fragmentation analysis is required
Everett, T.S., J. Chem. Educ. 1998, 75,

12. Also Adopted Isolation of Essential Oils from various spices
Pavia, D.L.; Lampman, G.M.; Kriz, G.S.; Engel, R.G. Introduction to Organic Laboratory Techniques, A Microscale Approach, Third Edition; Saunders: Philadelphia, 1999; pp
Chlorination Reactivity Ratios for Methylcyclohexane
Bishop, R.D., Jr., J. Chem. Educ. 1995, 72,

13. Also Modified Acetylation of Ferrocene
Amenta, D.S.; DeVore, T.C.; Gallaher, T.N.; Zook, C.M.; Mosbo, J.A.,
J. Chem. Educ. 1996, 73,

14. Also Tried Preparation of a C-4 or C-5 Acetate Ester
Pavia, D.L.; Lampman, G.M.; Kriz, G.S.; Engel, R.G. Introduction to Organic
Laboratory Techniques, A Microscale Approach, Third Edition; Saunders:
Philadelphia, 1999; pp
McGoran E.C.; Melton, C.; Taitch, D., J. Chem. Educ. 1996, 73, 88-92

15. Conclusions
There exist a wide range of experiments which already incorporate GC/MS.
There are a wide range of experiments which can be modified to incorporate GC/MS.
GC/MS is a modern structurally-based characterization technique that can be introduced early in the organic course and developed across both semesters.

16. Acknowledgements
National Science Foundation, Division of Undergraduate Education
Organic lab students at KU
Colleagues and lab instructors at KU

17. References
Kjonaas, R.A.; Soller, J.L.; McCoy L.A., J. Chem. Educ. 1997, 74,
Sherren, A. T. Presented at The American Chemical Society National Meeting, Boston, MA, 1999.
Rubinson, J.F.; Neyer-Hilvert, J., J. Chem. Educ. 1997, 74,
Everett, T.S., J. Chem. Educ. 1998, 75,
Pavia, D.L.; Lampman, G.M.; Kriz, G.S.; Engel, R.G. Introduction to Organic Laboratory Techniques, A Microscale Approach, Third Edition; Saunders: Philadelphia, 1999; pp
Amenta, D.S.; DeVore, T.C.; Gallaher, T.N.; Zook, C.M.; Mosbo, J.A., J. Chem. Educ. 1996, 73,
Bishop, R.D., Jr., J. Chem. Educ. 1995, 72,
Pavia, D.L.; Lampman, G.M.; Kriz, G.S.; Engel, R.G. Introduction to Organic Laboratory Techniques, A Microscale Approach, Third Edition; Saunders: Philadelphia, 1999; pp
McGoran E.C.; Melton, C.; Taitch, D., J. Chem. Educ. 1996, 73, 88-92