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Solving Qualitative Organic Problems with the Aid of an Automated Isotope-Pattern Analyzer

20 th Biennial Conference on Chemical Education Indiana University, Bloomington, Indiana, July 27, 2008. Solving Qualitative Organic Problems with the Aid of an Automated Isotope-Pattern Analyzer. Ray A. Gross, Jr. Prince George’s Community College. Introduction.

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Solving Qualitative Organic Problems with the Aid of an Automated Isotope-Pattern Analyzer

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  1. 20th Biennial Conference onChemical EducationIndiana University, Bloomington, Indiana, July 27, 2008

  2. Solving Qualitative Organic Problems with the Aid of an Automated Isotope-PatternAnalyzer Ray A. Gross, Jr. Prince George’s Community College

  3. Introduction • Many aryl compounds contain small combinations of Br, Cl and S atoms. • The Br, Cl, S stoichiometry of most of these compounds is revealed in their characteristic molecular-ion peaks in their low-resolution mass spectra • An automated isotope-pattern analyzer has been developed that determines the A + 2 composition of these compounds.

  4. Outline • Three qual-organic problems will be solved with the aid of the IPA. • The IPA will be demonstrated.

  5. Problem 1 What is the Br, Cl, S composition? Spectrum: Spectral Database for Organic Compounds, SDBS

  6. Problem 1 What is the Br, Cl, S composition? M = 288 (11.5%) M + 2 = 290 (8.5%) M + 4 = 292 (2.0%) Spectrum: Spectral Database for Organic Compounds, SDBS

  7. 3,4-toluenedisulfonyl dichloride

  8. Problem 2Compound A: mp 82 oC

  9. Compound A: Cl3

  10. CompoundA: 2,4,6-trichlorotoluene

  11. Problem 3

  12. Compound A: Cl3S1

  13. Compound B: Cl2S1

  14. Compound A: 2,4-dichlorobenzenesulfonyl chloride

  15. Conclusion • The IPA is a useful tool for qualitative organic analysis. • Finds A + 2 compositions for 21 combinations of Br, Cl and S. J. Chem Educ., 200784, 987-991

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