DGD12_NZ

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Chemistry

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Nov 24, 2024

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1 uOttawa.ca CHM3122: Applications of Spectroscopy • DGD12, Dec 5 th , 2023 Presented by: Niayesh Zarifi

2 nzarifi@uottawa.ca The 1 H NMR of this compound should have four signals. Predict the splitting pattern (singlet, doublet, doublet of doublets, etc) you would see for each signal.

3 nzarifi@uottawa.ca Here are the IR, 13 C NMR, and 1 H NMR spectra for an unknown with the formula C 6 H 10 O 2 . Identify the compound.

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4 nzarifi@uottawa.ca Based on the 1 H NMR data given, what is the structure and stereochemistry? The formula is C 8 H 16 O 4 . Resonances marked with asterices (*) exchange upon addition of D 2 O. 1.33 (d, J = 6Hz, 3H), 1.61 (d*, J = 4.0 Hz 1H), 1.87 (ddd, J = 14, 3.5, 3.4 Hz, 1H) 2.21 (ddd, J = 14.0, 3.0, 1.5 Hz, 1H) 2.87 (dd, J = 10.0, 3.0 Hz, 1H) 3.40 (s, 3H), 3.47 (s, 3H) 3.47 (s, 3H) 3.99 (dq, J = 10.0, 6.0 Hz, 1H) 4.24 (dddd, J = 4.0, 3.0, 3.0, 3.4 Hz, 1H) 4.79 (dd, J = 3.5, 1.5 Hz, 1H)

5 nzarifi@uottawa.ca Identify the following pyrrole C 8 H 9 NO paying attention to stereochemistry. Identify the chemical shifts and coupling constants (2 isomers possible).

6 nzarifi@uottawa.ca Assign all of the signals in the 1H NMR spectrum of the compound shown below. The solvent was CDCl3. Note: The labels C, H and I are not used.

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7 nzarifi@uottawa.ca Deduce the structure below that has the formula C4H9Br and use the 2D spectra HMQC & COSY to assign all the signals.

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