Unit%206_32_2008 - a RX and N 3 followed by reduction b...

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CHEMISTRY 0320 - ORGANIC CHEMISTRY II Prof. C. S. Wilcox - University of Pittsburgh Unit 6 Reading: Chapter 21 In this unit the chemistry of amines was discussed. The basicity and nucleophilicity of the amino group are quintessential features of the amines. I. Amine Basicity . a. Amines may be protonated. They are also Lewis acids. The basicity of an amine may be quantified by the acidity of the conjugate acid of the amine. The conjugate acid of an aliphatic amine has a pKa or about 10. b. Nitrogen atoms in imines, and amino groups attached to aromatic rings are much less basic than amino groups attached to alkanes. Why is this? II. Mechanisms. a. Hofmann elimination (an E2 process). b. Mannich reaction. (page 978) III. Preparation of amines
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Unformatted text preview: . a. RX and N 3 , followed by reduction. b. Gabriel synthesis. c. Reductive amination. d. Reduction of amides. e. Reduction of nitriles. f. Hofmann rearrangement. g. Reduction of nitro groups. III. Reactions of amines. Earlier units included discussion of amine acylation and alkylation. In addition, recall that amines may be used to form imines. A new reaction in this unit is the reaction of nitrous acid (HONO) and nitrosonium ions (NO + ) with amines. Know the products to be expected in the reaction of: a. HONO with primary amines. b. HONO with secondary amines. IV. Miscellaneous . a. The Hofmann Elimination was described and used to establish amine structure....
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