有機化學第20章_2009 [&

有機化學第20章_2009 [&

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2009/5/7 1 Chapter 20: Carboxylic Acids 羧酸 and and Nitriles Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula -C(=O)OH, usually written -COOH or -CO 2 H. Based on McMurry’s Organic Chemistry , 7 th edition A nitrile is any organic compound which has a -C N functional group The Importance of Carboxylic Acids (RCO 2 H) Starting materials for acyl derivatives (esters amides and acid chlorides (esters, amides, and acid chlorides) 2 Abundant in nature from oxidation of aldehydes and alcohols in metabolism
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2009/5/7 2 Why this Chapter? Carboxylic acids present in many industrial processes and most biological processes They are the starting materials from which other acyl derivatives are made 3 An understanding of their properties and reactions is fundamental to understanding organic chemistry OUTLINE ± Naming Carboxylic Acids and Nitriles St t d P ti f C b li A id ± Structure and Properties of Carboxylic Acids ± Biological Acids and the Henderson-Hasselbalch Equation ± Substituent Effects on Acidity ± Preparation of Carboxylic Acids ± Reactions of Carboxylic Acids: An Overview ± Chemistry of Nitriles ± Spectroscopy of Carboxylic Acids and Nitriles 4
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2009/5/7 3 20.1 Naming Carboxylic Acids and Nitriles If derived from open-chain alkanes, replace the terminal -e of the alkane name with -oic acid The carboxyl carbon atom is C1 5 Alternative Names Compounds with CO 2 H bonded to a ring are named using the suffix carboxylic acid using the suffix - The CO 2 H carbon is not itself numbered in this system 6
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2009/5/7 4 Common names I 7 Common names II 8
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2009/5/7 5 Nitriles, RCN Closely related to carboxylic acids named by adding - nitrile as a suffix to the alkane name, with the nitrile carbon numbered C1 Complex nitriles are named as derivatives of carboxylic acids. Replace - ic acid or - oic acid ending with - onitrile 9 P. 20.1
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2009/5/7 6 P. 20.1 P. 20.2
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2009/5/7 7 20.2 Structure and Properties of Carboxylic Acids Carboxyl carbon sp 2 hybridized: carboxylic acid groups are planar with C–C=O and O=C–O bond
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This note was uploaded on 11/11/2010 for the course CHE CH2005 taught by Professor 曹恒光 during the Spring '10 term at National Central University.

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有機化學第20章_2009 [&

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