Experiment : An Aerobic Alcohol Oxidation Using a Copper (I)/TEMPO Catalyst In t

Question

Experiment : An Aerobic Alcohol Oxidation Using a Copper (I)/TEMPO Catalyst

In this experiment, CuBr, 2,2 bipyridine, N-methyl imidazole and TEMPO was used to convert benzyl alcohol to aldehyde.

What evidence would appear in the product IR spectra indicating over-oxidization of the aldehyde?

3344.73 2858.11 1687.97 1586.88 1572.17 1479.75 13 34 1288.75 120331 115315 1007.33 949.49 831.41 807.85 791.93 686.60 624.80 utORS CHAT MacBook Pro Tue Nov 29 10:36:56 2016 (GMT-05:00) 505 40 4000 3500 3000 2500 2000 1500 1000 Wavenumbers (cm-1) 29 10:48:55 2016 (GMT-05:00)

Explanation / Answer

The over oxidation of aldehyde (benzaldehyde, CHO) will result into a carboxylic acid (benzoic acid, COOH).

So, the stretching of carbonyl group C=O will appear at 1690 cm-1 rather than 1700 cm-1 in aldehyde.

Additionally, a broad peak for O-H stretching is also appears from 3200-3500 cm-1 which is not expected for aldehyde functionalty.

Further, two peaks at 2700-2760 and 2800-2860 cm-1 is observed for C-H of akdehyde O=C-H bond which is not expected in carboxylic acid.

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