Chapter 17 (Lecture #14)

Chapter 17 (Lecture #14) - Chapter 17: Carboxylic Acids and...

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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 Chapter 17: Carboxylic Acids and their Deriva9ves Nucleophilic Addi9on-Elimina9on at the Acyl Carbon
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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
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Chapter 17 (Lecture #14) - Chapter 17: Carboxylic Acids and...

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