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Infrared Spectroscopy, Questions from Organic Chem 2 1. If you have an amine compound, how can...

Infrared Spectroscopy, Questions from Organic Chem 2

1. If you have an amine compound, how can you tell if it is primary, secondary, or tertiary by only looking at the 3300-3000 cm^-1 region?

2. Aldehyde (1740-1720 cm^-1) and Amide (1690-1640 cm^-1), both have carbonyls but they show up at different wavelengths. What, Chemically causes the difference?

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Answer #1

1. If the compound shows two N-H stretching bands in the given range, then the amine is primary whereas if it shows only one band, then the amine is secondary. Tertiary amines will not show any N-H bands.

2. In case of amide, the lone pair on nitrogen atom is involved in conjugation with the carbonyl system as a result of which it's double bond character decreases. This decreases the stretching vibrational frequency of the carbonyl group & thus, the wavelength of amide is lower than that of aldehyde where no such conjugation effect is present.

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