Problem: The following compound is an amino acid derivative (Chapter 25). In solution, molecules of this compound show a tendency to “stick” together, or self-assemble, via a series of intermolecular hydrogen bonds. During self-assembly, the growing aggregate can entrap molecules of liquid, thereby forming a gel (J. Am. Chem. Soc. 2009, 131, 11478–11484). (a) Each of the six hydrogen atoms bound directly to nitrogen can form a hydrogen bond, but H’s that are on the amides can form stronger hydrogen bonds than H’s on the amines. Explain why this is so using resonance.

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The following compound is an amino acid derivative (Chapter 25). In solution, molecules of this compound show a tendency to “stick” together, or self-assemble, via a series of intermolecular hydrogen bonds. During self-assembly, the growing aggregate can entrap molecules of liquid, thereby forming a gel (J. Am. Chem. Soc. 2009131, 11478–11484)

(a) Each of the six hydrogen atoms bound directly to nitrogen can form a hydrogen bond, but H’s that are on the amides can form stronger hydrogen bonds than H’s on the amines. Explain why this is so using resonance.

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Our data indicates that this problem or a close variation was asked in Organic Chemistry - Klein 2nd Edition. You can also practice Organic Chemistry - Klein 2nd Edition practice problems.