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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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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 C5H9ClO formed • What is the structure?
Step 2: Pieces • Based on integration, MF • Degrees of unsaturation for C5H9ClO = 1 A = -CH2- B = -CH2- C = -CH2- D = -CH3
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
Step 4: Test proposed structure • Does proposed structure match data?
Problem 3: C10H14O ether • What should you do with 7ppm and 7.3ppm? • Signal at 1.9ppm: hard to tell how many peaks