An organic compound was synthesized in the laboratory. The compound is known to contain three functional groups - an alcohol, an alkene, and an ester. Using IR spectroscopy, a broad peak was observed in the region between 3200-3400 cm^-1, which indicates the presence of the alcohol group. However, two different peaks were observed in the region between 1640-1680 cm^-1, which could correspond to either the alkene or ester group. Using other spectroscopic techniques such as NMR and mass spectrometry, determine the structure of the compound and identify which peak corresponds to the alkene or ester functional group.

Question

An organic compound was synthesized in the laboratory. The

Answer 1

To determine the structure of the compound and identify the peaks corresponding to the alkene and ester functional groups, we will use NMR  Nuclear Magnetic Resonance  spectroscopy and mass spectrometry.1. NMR spectroscopy: a  Proton NMR  1H-NMR : This technique will provide information about the number of protons in the molecule, their chemical environment, and their connectivity. Look for characteristic chemical shifts and coupling patterns that correspond to the alkene and ester groups. Alkene protons typically appear between 4.5-6.5 ppm, while ester protons  the ones attached to the carbonyl carbon  appear between 2.0-2.5 ppm. The alcohol proton will appear as a broad singlet between 1.0-5.0 ppm, depending on its environment.b  Carbon NMR  13C-NMR : This technique will provide information about the number of carbons in the molecule and their chemical environment. Look for characteristic chemical shifts that correspond to the alkene and ester groups. Alkene carbons typically appear between 110-150 ppm, while ester carbonyl carbons appear between 160-180 ppm. The alcohol carbon will appear between 50-90 ppm, depending on its environment.2. Mass spectrometry: This technique will provide information about the molecular weight of the compound and its fragmentation pattern. The molecular ion peak  M+  will give the molecular weight of the compound, which can help in determining the molecular formula. The fragmentation pattern can provide information about the connectivity of the functional groups and the overall structure of the compound.After analyzing the data from the NMR and mass spectrometry experiments, the structure of the compound can be deduced. The peaks observed in the IR spectroscopy between 1640-1680 cm^-1 can then be assigned to the alkene or ester functional group based on the structure. Typically, the ester carbonyl group  C=O  will have a peak around 1735-1750 cm^-1, while the alkene  C=C  will have a peak around 1640-1680 cm^-1. However, since the peaks are overlapping in this case, the NMR and mass spectrometry data will be crucial in assigning the correct functional group to each peak.