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Organic Chemistry | 2nd Edition | ISBN: 9781118454312 | Authors: David R. Klein
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For each pair of compounds, identify the stronger base. N

Chapter 23, Problem 23.41

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QUESTION:

For each pair of compounds, identify the stronger base. N N vs. (a) N N O (b) vs. HN H N HN NH (c) vs

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QUESTION:

For each pair of compounds, identify the stronger base. N N vs. (a) N N O (b) vs. HN H N HN NH (c) vs

ANSWER:

Step 1 of 3

(a) Let us consider the pair of compounds: pyridine with trimethylamine.

The nitrogen atom is compound 1 doesn’t need to use its lone pair of electrons to obtain aromaticity, as the already contains 6 pi electrons. However, recall that aromatic tertiary amines such as pyridine are not as basic as aliphatic tertiary amines, due in part to the isolation of their lone pair in an orbital perpendicular to the ring. Compound 2 is the strongest base of this pair. Its lone pair of electrons is fully localized on the nitrogen atom and has more freedom to reach out and attack a proton/Lewis acid.

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