Chapter 20 - Wade(1)

Chapter 20 - Wade(1) - Chapter 20 Carboxylic Acids St....

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Unformatted text preview: Chapter 20 Carboxylic Acids St. Johns University Dr. David P. Brown Introduction to General and Organic Chemistry III 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. => Chapter 20 3 Common Names Many aliphatic acids have historical names. Positions of substituents on the chain are labeled with Greek letters. CH 3 CH 2 CHC Cl OH O -chlorobutyric acid CH 3 CH 2 CH 2 CHCH 2 COOH Ph -phenylcaproic acid => 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 CH 2 CHC Cl OH O Ph C H C H COOH trans-3-phenyl-2-propenoic acid (cinnamic acid) => 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 COOH OH o- hydroxybenzoic acid (salicylic acid) => 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. => Chapter 20 7 Dicarboxylic Acids HOOCCH 2 CHCH 2 CH 2 COOH Br 3-bromohexanedioic acid -bromoadipic acid CO 2 H CO 2 H o-Phthalic acid Chapter 20 8 Structure of Carboxyl Group Carbon is sp 2 hybridized....
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This note was uploaded on 09/04/2011 for the course CHE 1130 taught by Professor Brown during the Fall '08 term at St. Johns Duplicate.

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Chapter 20 - Wade(1) - Chapter 20 Carboxylic Acids St....

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