CHM 424 Organic Analysis

Textbook: “Advanced Organic Spectroscopy Tools for Beginning Spectroscopists” by Phil Beauchamp (Amazon.com and Solutions)

Handouts (Syllabus, CHM 424L lab homepage), CHM 318L/319L Spectroscopy homepage

  • 1st Day Handout: Classical Methods of Analysis

  • IR Spectroscopy: IR Correlation Chart and Problem-Solving Approach | worksheet and answer key

  • Mass Spectrometry: lecture handout | answer key

  • C-13 NMR: lecture handout | chemical shift calculations (from Dr. Beauchamp): alkene C's and aromatic C's | H/C NMR tables for quiz/exam

  • Proton NMR: lecture handout | NMR 1-9 Key: Part 1 (puzzle pieces) and Part 2 (solutions) | chemical shift calculations (from Dr. Beauchamp): sp3 Hs and alkene Hs and aromatic Hs

  • 2D COSY NMR: lecture handout (better pdf version of first two pages) | additional in-class COSY example and solution

  • Midterm: blank copy and histogram (Note: extra credit can be earned by working on a blank exam and turning it in!)

  • NMR homework (solve a Chapter 8 problem and use spectra to ID carbons and hydrogens), due Monday, 11/27

  • Schedule for Weeks 9 and 10 (includes canceled lecture/lab 11/22 and lunch with faculty candidate 11/27 or 11/29)

  • Amino acid racemization article <>BR>

    Stereochemistry homework (specific rotation and ee calculations) and key


    Suggested textbook problems "Advanced Organic Spectroscopy Tools..." (Beauchamp, 2015/2017, Solutions)

  • Chapter 1 (DU): problems 3, 4 (p 22) (see also Wade section 7-3 "Elements of Unsaturation")
  • Chapter 2 (IR): all problems, 1-4 (pp 58-69)
  • Chapter 3 (MS): problems 5 (work on formulas a, b, e, and f only, p 82), 7 (logical peaks only, p 114), 8 (p 117)

    NMR (listed in order of lecture coverage):

  • Ch. 4, problem 1 (# signals, p 146)
  • Ch. 6, problems 2-4 (calculating sp2 C-13 shifts, pp 242-243)
  • Ch. 6, problems 5-13 (C-13 DEPT, pp 254-265)
  • Ch. 4, problems 2-4 (calculating H NMR chemical shifts, splitting patterns, J values, pp 149, 153, 178)
  • Ch. 4, problem 5 (#1-188! using H NMR with molecular formula to predict structure, pp 183-202)
  • Ch. 5, problem 6 (using COSY NMR to predict structure, pp 222-232)
  • Chapter 7 (1-page problems)
  • Chapter 8 (Complex Structure problems)

  • Resources

    ChemSpider - very cool database of chemicals (search by name, structure, CAS registry number, etc.) developed by the Royal Society of Chemistry

    SpectraSchool - interactive tutorials and problems on spectroscopy

    1H NMR tutorials and practice: ChemCalc Mass Spec calculator (determines possible formulas, given a molecular or fragment mass)
    "ChemCalc: a building block for tomorrow’s chemical infrastructure." Patiny, Luc; Borel, Alain
    Journal of Chemical Information and Modeling 201. DOI: http://dx.doi.org/10.1021/ci300563h

     

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    Last updated December 2, 2017