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Guided inquiry experiment demonstrates the iodination and esterification of benzaldehydes, suggesting effective organic synthesis in education.
Vanillin and ethyl vanillin are iodinated ortho to the hydroxyl group, when treated with sodium iodide and bleach in methanol. Under similar conditions, 4–methoxybenzaldehyde and 3,4–dimethoxybenzaldehyde are converted into the corresponding methyl esters. This guided–inquiry organic chemistry laboratory experiment requires students to correctly interpret proton NMR and IR spectra to deduce whether their benzaldehyde iodinated or formed a methyl ester.
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Hathaway et al. (2016) studied this question.
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