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Chapter 20 October 26

Chapter 20 October 26 - LiAlH 4 reduces carboxylic acids...

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1 Preparation of Carboxylic Acids Oxidation of an alkyl benzene to form benzoic acid Oxidative cleavage of an alkene (tri, di, monosubstituted)
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2 Preparation of Carboxylic Acids (cont'd): Oxidation of a primary alcohol or aldehyde Hydrolysis of nitriles
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3 Hydrolysis of Nitriles: Carboxylation of Grignard Reagents: Simple Mechanism: . Two step process that starts with an S N 2 reaction with an alkyl halide Be careful of competitive E 2 elimination reactions Primary alkyl halides work best Some unhindered secondary alkyl halides can work as well React a grignard reagent with CO 2
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4 Two Pathways to Phenylacetic Acid: Carboxylic Acid Reaction Overview:
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5 Reduction of Carboxylic Acids: Examples: Simple Synthesis Problem:
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Unformatted text preview: . LiAlH 4 reduces carboxylic acids but NaBH 4 does not BH 3 (Borane) in THF reduces carboxylic acids to primary alcohols [selective reduction] Used in preference to LiAlH 4 when sensitive groups are present 6 Chemistry of Nitriles Preparation Reactions: Similar in Reactivity to Carboxylic Acids We have seen the first prep method already: Additional Method: Dehydration of a Primary Amide Mechanism: Both the carboxylic acid carbonyl carbon and the nitrile carbon are electrophilic S N 2 reaction of KCN ( ­CN) with a primary alkyl halide 7 Reactions of Nitriles: The Anatomy of Nucleophilic Attack: Nitrile Reaction Overview:...
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