2. Determine the structure of a compound with a molecular formula of C6H12O and exhibits the following 'H NMR and 1³C NMR spectra. No peaks exchange in D2O. |= 6 | = 3 200 160 0.0 13 C NMR 1.1 1.0 | = 2 | = 1 2.6 2.5 9.e 8.0 7.e 6.0 5.0 4.0 3.0 2.0 1.0 e.e 1 H NMR

Use the 1H NMR and IR spectra given below to identify the structure of compound B (molecular formula C4H8O2).

Steps in Spectral Identification: •Identify major peaks in IR spectrum, if any. •Deduce structural fragments for each of the 1H NMR spectral signals. •Give the structure of the compound •Assign the signals in the 1H NMR spectra to specific protons •Assign carbons to the peaks in the 13C NMR spectrum Step 1. Calculate the degree of unsaturation for the unknown. Step 2. Determine the functional group from IR Step 3. Analyzing the MS spectrum Step 4. Analyzing the 1H NMR spectra Determine the number of different kinds of protons Step 5. Analyzing the 13C NMR spectra

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Please identify Molecule A, formed from the reaction shown, from the 13C NMR spectra shown. All peaks below are single peaks (no overlapping peaks). Inset is an expansion of the downfield section of the spectra.

The proton NMR and IR spectra of an unknown compounds is shown on the next page. Using the molecular formula C5H12O, find L a) the index of saturation b) the structure of the unknown compound c) assign the absorption bands to the functional groups in the IR spectrum d) label all peaks in the NMR spectrum, and label the same peak on the hydrogens in the structure Transmittance (%) 100 80 60 40 20 0 3500 CT TYCE Tabdf62 2874.30 2500 Wavenumber (cm-¹) 3000 2000 1466.09 1500 1307.78 1124.04 21 seser 908.46 1000 37.21

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¹H-NMR Spectra 3 M.F. = C₂H₁3NO 1 S 10 -00 8 6 PPM 4 N 21 3 ſ 2[2] -~ 2 3 j

8. Given the ¹H NMR spectrum provided, give the structure of the molecule. The IR shows two strong peaks at 1750 cm¹ and 3400 cm¹. The molecular formula is C3H6O2. Integrations are given below. —|- 10 1H 9 8 6 7 Chemical Shift (ppm) 1H 5 2H 3 2H 2

Steps in Spectral Identification: •Identify major peaks in IR spectrum, if any. •Deduce structural fragments for each of the 1H NMR spectral signals. •Give the structure of the compound •Assign the signals in the 1H NMR spectra to specific protons •Assign carbons to the peaks in the 13C NMR spectrum Step 1. Calculate the degree of unsaturation for the unknown. Step 2. Determine the functional group from IR Step 3. Analyzing the MS spectrum Step 4. Analyzing the 1H NMR spectra Determine the number of different kinds of protons Step 5. Analyzing the 13C NMR spectra