322bs10 Ch18 L16

322bs10 Ch18 L16 - Chapter 18 Carboxylic Acids and their...

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Chapter 18 Carboxylic Acids and their Derivatives: Nucleophilic Substitution at Acyl Carbon Carboxylic acids are a family of organic compounds with the functional group -C-OH O = also written as -CO 2 H or COOH The carbon-oxygen double bond is made up of a ! -bond and a " -bond. The carbon atom is sp 2 hybridized, which explains the trigonal planar geometry at this center. C O R HO ! " R may be alkyl, aryl or simply H
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Nomenclature of Carboxylic Acids Common names are frequently used for the simpler carboxylic acids that have been known for hundreds of years. HCOOH CH 3 COOH CH 3 CH 2 CH 2 COOH formic acid (from L. formica, or ant) acetic acid (from L. acetum, vinegar) butyric acid (from L. butyrum, butter) In common names, the positions of substituents are often given by ! , " , # .... C C C C COOH ! " # $ examples CH 3 CH 2 CHCOOH Cl ! -chlorobutyric acid CH 2 CH 2 COOH "# phenylpropionic acid
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Aromatic Acids: Benzoic Acids The carboxylic acids derived from benzene are named as derivatives of benzoic acid , using the standard notations to indicate positions of substituent groups. IUPAC Names The usual rules for this systematic naming system are used. The longest continuous chain with the carboxyl group is the parent. Drop the "e" in the alkane name and add "oic acid." Note: Count the carboxyl carbon as part of the parent chain. COOH benzoic acid COOH COOH NO 2 m-nitrobenzoic acid NO 2 Cl 2-chloro-4-nitrobenzoic acid
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examples CH 3 CH 2 CH 2 COOH butan oic acid CH 3 CHCH 2 CH 2 COOH CH 3 1 4-methylpentan oic acid CH 3 CHCOOH 2-phenylpropan oic acid CH 2 =CHCH 2 COOH 1 2 3 3-buten oic acid HCOOH CH 3 COOH methan oic acid ethan oic acid
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Salts of Carboxylic Acids A salt of a carboxylic acid is named by the cation (sodium, potassium, ammonium) followed by the acid with "ic acid" changed to "ate." CO 2 - Na + sodium benzo ate (CH 3 CH 2 CO 2 - ) 2 Mg 2+ magnesium propano ate
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The Acid Strength of Carboxylic Acids Carboxylic acids are weaker acids than mineral acids (HCl, HNO 3 , H 2 SO 4 ), but are more acidic than organic weak acids such as alcohols. Carboxylic acids are converted into their carboxylate salts by aqueous solutions of hydroxide. Aqueous solutions of mineral acids convert the salts
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This note was uploaded on 03/30/2010 for the course CHEM 322 B taught by Professor Singer during the Spring '09 term at USC.

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322bs10 Ch18 L16 - Chapter 18 Carboxylic Acids and their...

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