1058-RG5-10 - Chem 1058 J. Walcott LEARNING STRATEGIES...

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Chem 1058 J. Walcott LEARNING STRATEGIES CENTER Spring 2010 Review Guide #5 Lectures: 2/22/10 – 2/26/10 Chapter 16 I. Carboxylic Acids A carbonyl group is a carbon double bonded to an oxygen - an acyl group is a carbonyl group attached to an alkyl or aryl group. The characteristic functional group of carboxylic acids is the carboxy group (-CO 2 H). The carbonyl oxygen is part of the C=O double bond; the carboxylate oxygen is part of the C-O single bond. Acyl halides, acid anhydrides, esters and amides are carboxylic acid derivatives. They differ from carboxylic acid by the nature of the group that has replaced the -OH group of the carboxylic acid. A. Nomenclature Carboxylic acids are named systematically by dropping the final e from the name of the hydrocarbon with the same number of carbon atoms and adding the suffix –oic and the word acid . Please refer to your class notes for specific examples. B. Acid and Base Properties of Carboxylic Acids Carboxylic acids typically have pK a values between 4 and 5, but can be influenced significantly by inductive (polar) effects. Stabilization (electron withdrawing groups) on the conjugate base (carboxylate anion) strengthens the acidity. Destabilization (electron donating groups) on the conjugate base weakens the acidity. These trends are based on resonance and an inductive (polar) effect. The inductive effect is distance dependant. An electron withdrawing group will have a greater stabilizing effect with shorter distance from the carbonyl (ie. ortho vs para).
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This note was uploaded on 04/05/2010 for the course CHEM ORGANIC CH taught by Professor Dotsevisogah during the Spring '09 term at Cornell University (Engineering School).

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1058-RG5-10 - Chem 1058 J. Walcott LEARNING STRATEGIES...

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