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Magazine Chapter 16: Q67P (page 794)
Question: The only organic compound obtained when compound Z undergoes the following sequence of reactions gives the 1H NMR spectrum shown.
Identify compound Z.
Short Answer
Answer
From given 1H NMR spectrum it is clear that the compound contains aldehyde
(-CHO) functional group, because there is offset signal at 10.0 ppm, so the given compound is benzaldehyde. Therefore, Compound Z must be formaldehyde.
Step by step solution
1H NMR
Proton nuclear magnetic resonance (1H NMR) is the application of nuclear magnetic resonance in NMR spectroscopy with respect to hydrogen-1 nuclei within in the molecule of substance in order to determine the structure of its molecules.
Grignard Reaction
The Grignard reaction refers to an organometallic chemical reaction in which alkyl or aryl-magnesium halides known as Grignard reagent is added to C=O carbonyl group in ketones or aldehydes.This reaction is useful for the formation of carbon-carbon bonds. The chemical formula for Grignard reagent is R-Mg-X, where R is alkyl or aryl group, Mg is magnesium and X refers to halogen.
Identifying Compound Z
The Offset in given NMR spectra, shows that there is signal at 10.0 ppm, indicates aldehyde functional group.The 1H NMR spectra shown here, is of benzaldehyde.
Therefore, the treatment of phenylmagnesium bromide with a compound with one carbon to form an alcohol that can be further oxidized to benzaldehyde. Therefore, Compound Z must be formaldehyde, because it contains one carbon atom which reacts with phenylmagnesium bromide to give phenyl methanol, which further undergoes oxidation to produce benzaldehyde as shown in the figure given below:
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