Chapter 20 slides

Chapter 20 slides - Chapter 20 Carboxylic Acids...

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Chapter 20 Carboxylic Acids
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Chapter 20 2 Introduction • The functional group of carboxylic acids consists of a C=O with -OH bonded to the same carbon. • Carboxyl group is usually written -COOH. • Aliphatic acids have an alkyl group bonded to -COOH. • Aromatic acids have an aryl group. • Fatty acids are long-chain aliphatic acids. =>
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Chapter 20 3 Common Names • Many aliphatic acids have historical names. • Positions of substituents on the chain are labeled with Greek letters. CH 3 2 CHC Cl OH O α -chlorobutyric acid 3 2 2 CHCH 2 COOH Ph β -phenylcaproic acid =>
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Chapter 20 4 IUPAC Names • Remove - e from alkane (or alkene) name, add - oic acid . • The carbon of the carboxyl group is #1. CH 3 2 CHC Cl OH O 2-chlorobutanoic acid Ph C H C H COOH trans -3-phenyl-2-propenoic acid (cinnamic acid) =>
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Chapter 20 5 Naming Cyclic Acids • Cycloalkanes bonded to -COOH are named as cycloalkanecarboxylic acids. • Aromatic acids are named as benzoic acids. COOH CH(CH 3 ) 2 2- isopropylcyclopentanecarboxylic acid OH o - hydroxybenzoic acid (salicylic acid) =>
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Chapter 20 6 Dicarboxylic Acids • Aliphatic diacids are usually called by their common names (to be memorized). • For IUPAC name, number the chain from the end closest to a substituent. • Two carboxyl groups on a benzene ring indicate a phthalic acid. HOOCCH 2 CHCH 2 CH 2 COOH Br 3-bromohexanedioic acid β -bromoadipic acid =>
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Chapter 20 7 Structure of Carboxyl • Carbon is sp 2 hybridized. • Bond angles are close to 120 ° . • O-H eclipsed with C=O, to get overlap of π orbital with orbital of lone pair on oxygen. =>
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Chapter 20 8 Boiling Points Higher boiling points than similar alcohols, due to dimer formation.
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This note was uploaded on 04/08/2008 for the course CHEM 224 taught by Professor Pearson during the Spring '08 term at Case Western.

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Chapter 20 slides - Chapter 20 Carboxylic Acids...

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