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chapter20 - Chapter 20: Carboxylic Acids and Nitriles Based...

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Chapter 20: Carboxylic Acids and Nitriles Based on McMurry’s Organic Chemistry , 7 th edition
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3 The Importance of Carboxylic Acids (RCO 2 H) Starting materials for acyl derivatives (esters, amides, and acid chlorides) Abundant in nature from oxidation of aldehydes and alcohols in metabolism Acetic acid, CH 3 CO 2 H, - vinegar Butanoic acid, CH 3 CH 2 CH 2 CO 2 H (rancid butter) Long-chain aliphatic acids from the breakdown of fats
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4 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 An understanding of their properties and reactions is fundamental to understanding organic chemistry
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5 20.1 Naming Carboxylic Acids and Nitriles Carboxylic Acids, RCO 2 H If derived from open-chain alkanes, replace the terminal -e of the alkane name with -oic acid The carboxyl carbon atom is C1
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6 Nomenclature Priorities: Nomenclature Priorities: Highest priority at Highest priority at top of table and lowest priority at the bottom. top of table and lowest priority at the bottom. Function Group Suffix Name Prefix Name carboxylic acids -oic acid ? aldehydes -al oxo ketones -one oxo alcohols -ol hydroxy phenols -ol hydroxy thiols -thiol mercapto alkenes -ene alkenyl alkynes -yne alkynyl alkanes -ane alkyl
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7 Carboxylic Acid Nomenclature (RCO Carboxylic Acid Nomenclature (RCO 2 2 H) H) Prefix name = Prefix name = Suffix Name = oic acid Suffix Name = oic acid Compound Compound IUPAC Name IUPAC Name Common Name Common Name HCO 2 H methanoic acid formic acid (formica – ants) CH 3 CO 2 H ethanoic acid acetic acid (vinegar) CH 3 CH 2 CO 2 H propanoic acid propionic acid CH 3 CH 2 CH 2 CO 2 H butanoic acid butyric acid (rancid butter) CH 3 CH 2 CH 2 CH 2 CO 2 H pentanoic acid valeric acid (valerianenceae -plant) CH 3 CH 2 CH 2 CH 2 CH 2 CO 2 H hexanoic acid caproic acid (goat sweat) Know how to use IUPAC rules and the common names in red type.
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8 Carboxylic Acid Nomenclature (RCO Carboxylic Acid Nomenclature (RCO 2 2 H) H) Prefix name = Prefix name = Suffix Name = oic acid Suffix Name = oic acid Compound Compound IUPAC Name IUPAC Name Common Name Common Name PhCO 2 H benzene carboxylic acid benzoic acid HO 2 CCO 2 H ethanedioic acid oxalic acid HO 2 CCH 2 CO 2 H propanedioic acid malonic acid HO 2 C-Ph-CO 2 H benzene-1,4- dicarboxylic acid teraphthalic acid CH 2 =CHCO 2 H propenoic acid acrylic acid Know how to use IUPAC rules and the common names in red type.
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9 Carboxylic Acid Nomenclature (RCN) Carboxylic Acid Nomenclature (RCN) Prefix name = cyano Prefix name = cyano Suffix Name = nitrile Suffix Name = nitrile Compound Compound IUPAC Name IUPAC Name Common Name Common Name HCN hydrogen cyanide CH 3 CN ethanenitrile acetonitrile CH 3 CH 2 CN propanenitrile CH 3 CH 2 CH 2 CN butanenitrile Ph-CN benzonitrile Know how to use IUPAC rules and the common names in red type.
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10 Table 20-1a, p. 753
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11 Table 20-1b, p. 753
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This note was uploaded on 04/07/2008 for the course CHGN 222 taught by Professor Cowley during the Spring '08 term at Mines.

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chapter20 - Chapter 20: Carboxylic Acids and Nitriles Based...

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