ch 19 - CHAPTER 19 Carboxylic Acids Replace the ending e in...

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CHAPTER 19 Carboxylic Acids Replace the ending e in the alkane by the ending Replace the ending –e in the alkane by the ending –oic acid .
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The carboxyl group is planar. As neat liquids, and even in solutions, carboxylic acids -1 form hydrogen bonded dimers (6 8 kcal mol ). The carboxy function is strongly polar and forms hydrogen bonds to other polarized molecules such as water, alcohols and other carboxylic acids. Carboxylic acids up to butanoic acid are completely Carboxylic acids up to butanoic acid are completely soluble in water.
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Carboxylic acids have high melting and boiling points due to hydrogen bonding in both the solid and liquid states. Electron-withdrawing substituents increase the acidity of carboxylic acids.
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Important Concepts Carboxylic acids are acidic because - polarized C=O is electron withdrawing deprotonation gives resonance stabilized - deprotonation gives resonance-stabilized anions Electron withdrawing groups increase acidity - effect wears off with increasing distance Protonation occurs at the carbonyl oxygen - requires strong acid - resonance-stabilized cation Primary alcohols oxidize first to aldehydes, which then may further oxidize to carboxylic acids. Oxidants include CrO 2 , KMnO 4 and HNO 3 .
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A two step synthesis of carboxylic acids: conversion of an alkyl halide into the corresponding carboxylic acid having one more carbon.
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ch 19 - CHAPTER 19 Carboxylic Acids Replace the ending e in...

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