ASUC chem 26 - CHEMISTRY 3B Professor Peter Vollhardt...

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Professor Peter Vollhardt 11/25/08 Lecture 26 ASUC Lecture Notes Online is the only authorized note-taking service at UC Berkeley. Do not share, copy or illegally distribute (electronically or otherwise) these notes. Our student-run program depends on your individual subscription for its continued existence. These notes are copyrighted by the University of California and are for your personal use only. D O N O T C O P Y Sharing or copying these notes is illegal and could end note taking for this course. LECTURE Reactions of sugars 1. Oxidation a) CHO Æ COOH (aldose Æ aldonic acid) b) Alpha-hydroxy group of ketoses Æ alpha- dicarbonyl Large scale preparation of aldonic acids: Br 2 , H 2 O Dehydration gives lactones, typically five- membered (gamma-lactones), by kinetic control. c) Oxidation of both ends of aldoses Æ aldaric acid Note the selectivity of nitric acid: picks on primary OH function (after oxidizing the formyl group): less hindered. For some sugars, this oxidation may give meso
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This note was uploaded on 10/07/2010 for the course CHEM 3b taught by Professor Pederson during the Fall '08 term at University of California, Berkeley.

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ASUC chem 26 - CHEMISTRY 3B Professor Peter Vollhardt...

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