CH4/535

Links to material used in lecture

• Week 1: Mass Spectrometry. Reading: McLafferty, Ch. 1-3 (eventually 4-5 also)
  Mass spec powerpoint file
• Week 2: IR spectroscopy. Reading: Pretsch, IR tables.
  
  • IR Instrumentation
  • Basic IR interpretation
  • Animations of molecular vibrations corresponding to IR absorbances
  • Carbonyl stretches
  • C-H stretches
  • Effect of H-bonding on O-H stretch
  • Aromatic substitution and out-of-plane stretches
• Week 3: ¹H NMR spectroscopy. Reading: Claridge, Chs. 1-3; Pretsch ¹H NMR tables.
• 1-Phenyl-2-butanone
  
• 4-Phenyl-2-butanone
  
• 1-Nitropropane
• Methyl Propionate
• 3-methyl-but-2-en-1-ol
• Assigning ¹H NMR spectra for a variety of simple compounds.
• Week 4: ¹³C NMR spectroscopy. Reading: Claridge, Ch. 4; Pretsch ¹³C NMR tables.
C₅H₁₀O isomers
Isomers of methoxybenzoic acid
Assignment of spectra for a variety of simple compounds.
• Week 5: Polarization transfer experiments
DEPT spectra and Butylbenzene:

Comparisons from earlier HW problems:

• 2-pentanol
• Methoxystyrene
• Diphenylbromocyclopropane
• Week 6: 2D corelation spectroscopy. Reading: Claridge Ch. 5.
  
• Bromopentene:  introduction to looking at COSY spectra
  
• Propylene carbonate
• p-Methoxystyrene
• Phase-sensitive, double quantum filtered COSY of Bromopentene
• Slices: File 1 File 2
• Week 7: Multinuclear correlation and inverse detection (HSQC). Reading: Claridge Ch. 6.
Propylene Carbonate
Slices:
• 20 ppm
• 71.1 ppm
• 74 ppm
More complex problems: disubstituted aromatics. Ortho or meta?

Norcamphor

TOCSY of cyclooctylamine:

• COSY spectrum
• "Normal" HSQC
• HSQC-TOCSY 20 msec spin lock
• HSQC-TOCSY 40 msec spin lock
• HSQC-TOCSY 80 msec spin lock
• Week 8: Long-range coupling and HMBC spectra.
p-Methoxystyrene
9,10-phenanthroline

• Week 9: Nuclear Overhauser enhancement. Reading: Claridge Ch. 8.
  A problem assigning substitution regiochemistry
  Stereochemical analysis of two metal complexes
  Cinchonine: NOESY
  ROESY Structure: cinchonine.pdb
  Ref. to a structure paper by Dr. Gerwick: https://dx.doi.org/10.1021/np010526c and supporting information. (Off-campus users: refer to the Valley Library proxy server instructions to access this electronically, or find J. Nat. Prod., 2002, 65, 925-928 in the stacks.
  Compound structure
• Week 10: Dynamic NMR (Page 1, Page 2 ), Mosher esters for assignment of absolute configuration, solvent effects, and any other fun stuff I can come up with examples for.