L_4_09 - products of over-alkylation. The imine...

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318N – Krische, Lecture 4: Th - 01/29/09, Ch. Aldehyde and Ketones The condensation of a primary amine with an aldehyde or ketone leads to an imine (also known as a Schiff base). The condensation of secondary amines with aldehydes or ketones provides enamines. We saw that the mechanism for imine/enamine formation was similar to ketal formation up until the last two steps. We compared all three mechanisms and noted their similarities. Imines can be hydrogenated using Ni/H2 to give the corresponding amines. Thus, imine formation- hydrogenation sequences are routes to primary and secondary amines (in the former case, NH3 is used and in the latter case RNH2 is used). Preparation of secondary amines via alkylation of a primary amine using an SN2 process results in
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Unformatted text preview: products of over-alkylation. The imine formation-hydrogenation sequence avoids this problem. Some problems in synthesis were discussed that allowed us to refresh our memory of some key reactions from 310M (epoxidation, H 2 CrO 4 oxidation, ozonation, E 2-elimination). Be sure to know the mechanisms for ketal/acetal, dithiane, imine and enamine formation and hydrolysis. The Wolff-Kishner Reduction was discussed and we reviewed the mechanism. The Clemmenson reduction was discussed. The oxidation of aldehydes employing sliver oxide was discussed. The Baeyer-Villiger oxidation was discussed and we reviewed the mechanism....
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This note was uploaded on 03/31/2009 for the course CH 318M taught by Professor Bocknack during the Spring '08 term at University of Texas at Austin.

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