Answered: 18. 2-Aminopyridine can be nitrated or…

18. 2-Aminopyridine can be nitrated or sulfonated under much milder conditions than pyridine itself; substitution occurs chiefly at the 5-position. Account for these facts.

Chemistry for Today: General, Organic, and Biochemistry

9th Edition

ISBN:9781305960060

Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen

Publisher:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen

Chapter16: Amines And Amides

Section: Chapter Questions

Problem 16.68E

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Organometallic Compounds of s- and p- block elements

Organometallic compounds have a minimum of one bond between a metal compound and a carbon atom. Metalloid elements such as silicon, tin, and boron form organometallic compounds which can be utilized in a few commercial chemical reactions.

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18. 2-Aminopyridine can be nitrated or sulfonated under much milder
conditions than
pyridine itself; substitution occurs chiefly at the 5-position. Account
for these facts.

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22.47 Tertiary amines with three different alkyl groups are chiral but cannot be resolved because pyramidal inversion causes racemization at room temperature. Nevertheless, chiral aziridines can be resolved and stored at room temperature. Aziridine is a three-membered heterocycle containing a nitrogen atom. The following is an example of a chiral aziridine. In this compound, the nitrogen atom is a chiral center. Suggest a reason why chiral aziridines do not undergo racemization at room temperature.
Treatment of 1,3,6-cyclononatriene (Compound 1), or its dimethyl derivative (Compound 2), with potassium amide (KNH₂) in liquid ammonia results in the formation of anion 1a or 2a, respectively (J. Am. Chem. Soc. 1973, 95, 3437-3438): 9 15.85a 2 6 3 4 5 Compound 1 (R=H) Compound 2 (R=CH3) * You answer is incorrect. KNH₂ KNH₂ 1a (anion) 2a (anion) Of the following, which is NOT one of the four resonance structures of 1a?