The next two pages show two sets of 13 C and 1 H NMR spectra. In both sets of sp

Question

The next two pages show two sets of 13C and 1H NMR spectra. In both sets of spectra, the triad at 77 ppm in the 13C NMR spectra and the peak at 7.26 ppm in the 1H NMR spectra are due to the solvent.

a) The first set of spectra is of a compound whose fomula is C10H12O. Determine the structure of the compound giving rise to these spectra.

b) The second set of spectra is of a compound whose fomula is C5H9NO4. Determine the structure of the compound giving rise to these spectra.

c) Draw the product of the reaction if the two molecules from parts (a) and (b) above were to react via an aldol condensation.

Explanation / Answer

The compound (a) is 3,4,5-trimethylbezaldehyde and compound (b) is ethyl-2-nitropropanoate. they will react to form ethyl 3-hydroxy-2-methyl-2-nitro-3-(3,4,5-trimethylphenyl)propanoate.

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