Chapter_20_Reactions

Chapter_20_Reactions - R OCH 3 O CH 2 N 2 N 2 5 Reaction...

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Chem 358 – Prelim 2 Review Reactions (Chapters 20 Chapter 20 – Chemistry of Carboxylic Acids Know detailed mechanisms for 4, 7 and 9 R OH O .. .. .. .. .. .. + H 2 O R O O .. .. R O O .. .. + .. H 3 O R OH O .. .. .. H 3 O + R O O .. .. H H R O O .. .. H H .. + H 2 O 1. Acidity of Carboxylic Acids 2. Basicity of Carboxylic Acids Synthesis RCH 2 OH Oxidizing agent RCOOH RCHO Oxidizing agent RCOOH Oxidizing agents: aqueous CrO 3 , KMnO 4 , K 2 Cr 2 O 7 , Na 2 Cr 2 O 7 Oxidizing agents: aqueous CrO 3 , KMnO 4 , K 2 Cr 2 O 7 , Na 2 Cr 2 O 7 , Ag + Carbonation of Grignard reagents and organolithium compoumnds R—MgX + CO 2 THF R—COO - + MgX .. H 3 O R—COOH R—Li + CO 2 THF R—COO - Li + .. H 3 O R—COOH CH 2 R KMnO 4 vigorous COOH Side-chain oxidation of alkylbenzenes Reactions R OH O .. .. + E—Nu R Nu O + HO—E General R OH O .. .. SOCl 2 or PCl 5 + R Cl O 3. Formation of acid chlorides R O O .. .. H H
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Reactions - continued R OH O .. .. .. R'OH + H + R OR' O .. .. .. .. + H 2 O 4. Fischer Esterification
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Unformatted text preview: + R OCH 3 O .. .. + CH 2 N 2 N 2 5. Reaction with diazomethane to form methyl esters R'X + K 2 CO 3 R OR' O .. .. 6. Reaction of carboxylates with alkyl halides to form esters 7. Dehydration to form anhydrides R' O R O O .. .. + P 2 O 5 Heat COOH COOH POCl 3 O O O 8. Reduction to alcohols RCOOH 1. LiAlH 4 , ether 2. H 3 O + RCH 2 OH Note: NaBH 4 does not reduce carboxylic acids 9. Decarboxylation HOOC COOH R H Heat HOOC—CH 2 R R O R' COOH H R O H R' H Heat R OH O .. .. R OH O .. .. R OH O .. .. R OH O .. .. H + H +...
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Chapter_20_Reactions - R OCH 3 O CH 2 N 2 N 2 5 Reaction...

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