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Unformatted text preview: VATIVES The aldol condensation between two aldehydes to give a β-hydoxy aldehyde Nucleophilic acyl substitutions Anhydride preparations and reactions LiAlH4 R OH alcohols O CrO3 H+/heat O CrO3 R R H aldyhydes O R' OH carboxylic acids H+/ H2O R R + O H R 1 H3C 3 3 2 5 4 O R aldol reactions can occur intramoleuclarly to give cyclic products (favouring 5 or 6 membered rings) 2 1 H 4 5 H O Nucleophilic acyl substitutions Nu aldol products can dehydrate under acidic or basic conditions to give the conjugated product H O O amides Cl H O R H2O N H SOCl2 O R H w H2O OH R' R H O R nitriles O mild base H2O + + O esters R'NH2 H+ OH O H R N C R O anhydrides R R'OH H+ OH O O HO Nu Claisen condensation is similar to the aldol reaction, with esters as the starting material acid chlorides CARBOHYDRATES – (IGNORE IF NOT COVERED) PROPERTIES OH REACTIONS AND OEt OAc OAc ester formation OCH3 Ac2O pyridine OCH3 OCH3 ether formation NaBH4 R OH OH reduction OH Br2/H2O O HO HO OH OH mild oxidation O HO HO OH MeOH H+ OH HO HO OH CH3I Ag2O O OCH3 OH glycoside formation O O HNO3 HO O HO HO OEt OH O H3CO H3CO R OH OAc OH HO strong oxidation HO O mild base Fisher, Haworth and chair conformations Reactions, including Kiliani-Fisher and Wohl AcO AcO O O O OH OH PART IV – RADICAL α TO THE CARBONYL ENOLATE CHEMISTRY Enol tautomerization and structure Reactions at the α position of carbonyls (β) Elimination of malonic esters CARBONYL CONDENSATION REACTIONS Aldol condensation (mixed, intramolecular, etc) Claisen condensation (mixed, cyclizations, etc Our Course Booklets - free at prep sessions - are the “Perfect Study Guides.” OEt...
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This note was uploaded on 10/24/2011 for the course CHEMISTRY chem taught by Professor David during the Spring '11 term at The University of British Columbia.

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