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1559T_ch19_344-357 10/17/05 13:51 Page 344
19
Carboxylic Acids
The carboxylic acids and their derivatives contain a carbonyl group as one primary source of reactivity and
therefore have a lot in common with aldehydes and ketones. However, two major features make carboxylic
acids different from aldehydes and ketones. First, the HO proton is made much more acidic by the neighbor-
ing CPO function. Second, the HO may behave as a leaving group under the right conditions. You will dis-
cover the importance of this ability when you study nucleophilic additions to the carboxy group.
Outline of the Chapter
19-1 Naming the Carboxylic Acids
19-2, 19-3 Physical Properties of Carboxylic Acids
Very strongly hydrogen-bonding molecules; spectroscopy.
19-4 Acidity and Basicity of Carboxylic Acids
An analysis of resonance and inductive effects.
19-5, 19-6 Preparation of Carboxylic Acids
Reviewing some reactions you’ve seen before.
19-7 Reactivity of the Carboxy Group: Addition and Elimination
A new, general mechanism sequence.
19-8 Alkanoyl Halides and Anhydrides
19-9 Esters
19-10 Amides
Conversion of acids into their most important derivatives.
19-11 Nucleophilic Attack at a Carboxylate Group
Reactions of acids with hydride.
19-12 -Bromination
A reaction of special value in synthesis.
19-13 Carboxylic Acids in Nature
344
1559T_ch19_344-357 10/17/05 13:51 Page 345
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