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Using NMR Spectra to Identify Unknowns

Using NMR Spectra to Identify Unknowns. Identifying Unknowns. The Markovnicov product is the expected product Predict a proton NMR for the product:. What Product Was Formed?. Proton NMR not consistent Further analysis indicates C 5 H 9 ClO formed What is the structure?.

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Using NMR Spectra to Identify Unknowns

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  1. Using NMR Spectra to Identify Unknowns

  2. Identifying Unknowns • The Markovnicov product is the expected product • Predict a proton NMR for the product:

  3. What Product Was Formed? • Proton NMR not consistent • Further analysis indicates C5H9ClO formed • What is the structure?

  4. Step 1: Make data table

  5. Step 2: Pieces • Based on integration, MF • Degrees of unsaturation for C5H9ClO = 1 A = -CH2- B = -CH2- C = -CH2- D = -CH3

  6. Step 3: Link pieces together • Use Splitting • Use shift • Piece A must be connected to –Cl because of shift • Piece A must be connected to methylene because of n=2

  7. Step 4: Test proposed structure • Does proposed structure match data?

  8. Problem 1: C5H10O2 ester

  9. Problem 2: C10H12O2

  10. Problem 3: C10H14O ether • What should you do with 7ppm and 7.3ppm? • Signal at 1.9ppm: hard to tell how many peaks

  11. Problem 4: C7H12Cl2

  12. Problem 5: C10H14

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