Student%20Notes%20-%20Section%2016 - Section 16 Carboxylic...

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Section 16: Carboxylic Acids and their Derivatives 233 Section 16: Carboxylic Acids and Their Derivatives 16.1 Nomenclature 16.1.1 Nomenclature of Carboxylic Acids Carboxylic acids are named by replacing –e in the name of the parent compound with –oic acid . The carboxyl group in simple linear systems is labelled C1. In the case where the carboxyl group is substituted onto a ring system, the point of attachment to the ring is labelled C1. The compound is named for the parent ring with the suffix carboxylic acid . The group RCO- is called an acyl group, and is generally named according to the parent acid, by replacing –ic acid with – yl . Due to their common occurrence in nature, many carboxylic acids have trivial names, including long-chain fatty acids (LCFAs). HCOOH formic acid methanoic acid Acid Systematic Name Trivial Name CH 3 COOH acetic acid ethanoic acid CH 3 CH 2 COOH propionic acid propanoic acid CH 3 CH 2 CH 2 COOH butyric acid butanoic acid CH 3 (CH 2 ) 3 COOH valeric acid pentanoic acid CH 3 (CH 2 ) 4 COOH caproic acid hexanoic acid caprylic acid capric acid octanoic acid decanoic acid dodecanoic acid tetradecanoic acid hexadecanoic acid octadecanoic acid icosanoic acid lauric acid myristic acid palmitic acid stearic acid arachidinoic acid CH 3 (CH 2 ) 6 COOH CH 3 (CH 2 ) 8 COOH CH 3 (CH 2 ) 10 COOH CH 3 (CH 2 ) 12 COOH CH 3 (CH 2 ) 14 COOH CH 3 (CH 2 ) 16 COOH CH 3 (CH 2 ) 18 COOH Straight Chain & Saturated Fatty Acids Dicarboxylic Acids HOOC(CH 2 ) n COOH n = 0 oxalic acid malonic acid succinic acid glutaric acid adipic acid 1 2 3 4 Unsaturated Acids COOH R R = H R = CH 3 acrylic acid methacrylic acid COOH COOH maleic acid COOH HOOC fumaric acid Aromatic Acids COOH COOH COOH COOH HOOC benzoic acid phthalic acid terephthalic acid COOH 1-naphthoic acid
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Section 16: Carboxylic Acids and their Derivatives 234 16.1.2 Nomenclature of Nitriles Simple nitriles are named from the parent alkane, adding the suffix –nitrile to the end of the name. In the absence of other groups, the nitrile carbon is labelled as C1 in the parent chain. Where the –CN group is attached to a ring, the - carbonitrile suffix is used. Alternatively, the nitrile may be named as a derivative of the parent acid. In these cases, the –oic acid or –ic acid is replaced by –onitrile . These are formally trivial names, but are widely used. HCN hydrogen cyanide prussic acid CH 3 CN acetonitrile CH 3 CH 2 CN propionitrile CH 3 CH 2 CH 2 CN butyronitrile CH 3 (CH 2 ) 3 CN valeronitrile Straight Chain Nitriles Dinitriles NC(CH 2 ) n CN n = 1 malononitrile succinonitrile 2 Unsaturated Nitriles CN R R = H R = CH 3 acrylonitrile methacrylonitrile Aromatic Nitriles CN benzonitrile 16.1.3 Nomenclature of Esters Simple esters are named in two parts: the group bonded to the oxygen is named as an alkyl (or aryl) group and placed first, and the fragment containing the carbonyl group is named as a carboxylic acid, except that -ic acid is replaced by –ate . The carbonyl containing fragment is named last. Diesters are named in a similar fashion.
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Student%20Notes%20-%20Section%2016 - Section 16 Carboxylic...

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