Organic Chemistry

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15. Analytical Techniques:IR, NMR, Mass Spect

Structure Determination without Mass Spect

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concept

Building Molecular Sentences

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example

Building a molecular sentence

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Problem

Propose a structure for the following compound that fits the following 1H NMR data: 

Formula:C3H8O2                                                  1H NMR:3.36 δ (6H, singlet) 

                                                                                         4.57 δ (2H, singlet)

4
Problem

Propose a structure for the following compound that fits the following 1H NMR data: 

Formula:C2H4O2                                            1H NMR:2.1 δ (singlet, 1.2 cm) 

                                                                                   11.5 δ (0.5 cm, D2O exchange)

5
Problem

Propose a structure for the following compound that fits the following 1H NMR data: 

Formula:C10H14                                      1H NMR:1.2 ppm (6H, doublet) 

                                                                             2.3 ppm (3H, singlet) 

                                                                             2.9 ppm (1H, septet) 

                                                                             7.0 ppm (4H, doublet)

6
Problem

Propose a structure for the following compound, C7H12O2 with the given 13C NMR spectral data: 

Broadband decoupled 13C NMR:19.1, 28.0, 70.5, 129.0, 129.8, 165.78 δ 

DEPT-90:28.0, 129.8 δ 

DEPT-135:19.1 δ (↑), 28.0 (↑) , 129.8 δ (↑) , 70.5 δ (↓)&129.0δ (↓)

7
Problem

Propose a structure for the following compound, C5H10O with the given 13C NMR spectral data: 

Fully Broadband decoupled 13C NMR and DEPT:206.0 δ (↑); 55.0 δ (↑); 21.0 δ (↓)& 11.0 δ (↑).

8
Problem

Provide the structure of the unknown compound from the given information. 

Formula:C4H10O            IR:3200-3600 cm-1           1H NMR:0.9 ppm (6H, doublet) 

                                                                                               1.8 ppm (1H, nonatet) 

                                                                                               2.4 ppm (1H, singlet) 

                                                                                               3.3 ppm (2H, doublet)

9
Problem

Provide the structure of the unknown compound from the given information. 

Formula:C4H9N              IR:2950 cm-1, 3400 cm-1           1H NMR:1.0 ppm (4H, triplet) 

                                                                                                         2.1 ppm (4H, triplet) 

                                                                                                         3.2 ppm (1H, singlet)