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11-13-12 chapter 14 .docx

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Department
Chemistry
Course
CHEM 1161
Professor
Schlegel
Semester
Fall

Description
Chapter 14:Carboxylic Acids, Esters, Amides, Amines 11/13/2012 14.1 Carboxylic Acids  IUPAC Names for Carboxylic Acids 2 In the IUPAC names of carboxylic acids, • the -e in the alkane name is replaced with -oic acid CH 4 Methane HCOOH Methanoic acid CH 3—CH 3 Ethane CH 3—COOH Ethanoic acid • substituents are numbered from the carboxyl carbon 1 CH 3 O CH —CH—CH 2—C—OH 4 3 2 1 3-methylbutanoic acid Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition                        Aromatic Carboxylic Acids 6 Benzoic acid • is the simplest aromatic carboxylic acid • locates substituents by numbering the ring from carbon 1 in the carboxyl group Chemistry: An Introduction to General, Organic, and Copyright © 2012 by Pearson Education, Inc. Alpha Hydroxy Acids (AHAs) • naturally occurring carboxylic acids with a hydroxyl group adjacent (alpha) to the carbonyl group • Used in many skin care products to help improve skin texture, remove scars, etc. • 14.2 Properties of Carboxylic Acids  Polarity of Carboxylic Acids 10 Carboxylic acids are strongly polar because they have two polar groups hydroxyl (−OH) and carbonyl (C=O) Chemistry: An Introduction to General, Organic, and BCopyright © 2012 by Pearson Education, Inc. Solubility in Water Carboxylic acids •   form hydrogen bonds with many water molecules •   with up to four carbon atoms are very soluble in water •   as the number of carbons increases, the solubility of the carboxylic acid in water is reduced Acidity of Carboxylic Acids 12 • Carboxylic acids are weak acids • ionize in water to produce carboxylate ions and hydronium ions • can lose a proton because two oxygen atoms in carboxylate ion stabilize negative charge O O CH 3−C−OH + H 2O CH 3−C−O –+ H O + carboxylic acid carboxylate ion Chemistry: An Introduction to General, OrgCopyright © 2012 by Pearson Education, Inc.ition • stabilized by resonance­ negative charge of O2­ is distributed all throughout                           bond  Neutralization of Carboxylic Acids 13 Carboxylic acid salts • are a product of the neutralization of a carboxylic acid with a strong base CH 3—COOH + NaOH CH 3—COO –Na ++ H2O acetic acid sodium acetate (carboxylic acid salt) • are used as preservatives and flavor enhancers Chemistry: An Introduction to General, OrgCopyright © 2012 by Pearson Education, Inc.ition 14.3 Esters Esterification 16 Esterification is the reaction of a carboxylic acid and alcohol in the presence of an acid catalyst to produce an ester. The main chain of an ester comes from the carboxylic acid, while the alkyl group in an ester comes from the alcohol. Chemistry: An Introduction to General, Organic, and BiCopyright © 2012 by Pearson Education, Inc. Naming Esters 17 The name of an ester consists of two words derived from the name of the alcohol and the acid in that ester. 1. The first word indicates the alkyl part from the alcohol. 2. The second word is the carboxylate name of the carboxylic acid. Chemistry: An Introduction to General, Organic, andCopyright © 2012 by Pearson Education, Inc. Aspirin and Salicylic Acid 18 Aspirin • is used to relieve pain and reduce inflammation • is an ester of salicylic acid and acetic acid Oil of wintergreen • is used to soothe sore muscles • is an ester of salicylic acid and methanol Chemistry: An Introduction to General, Organic, anCopyright © 2012 by Pearson Education, Inc. Base Hydrolysis (Saponification) 19 Base hydrolysis, or saponification, • is the reaction of an ester with a strong base • produces the salt of the carboxylic acid and an alcohol O || CH 3—C—O—CH 2—CH 3 + NaOH O || CH —C—O –Na+ + HO—CH —CH 3 salt of carboxylic acid alcohol sodium acetate ethanol Chemistry: An Introduction to General, OrgaCopyright © 2012 by Pearson Education, Inc.tion Soaps­ products of base hydrolysis A soap •   contains a nonpolar end that dissolves in nonpolar fats and oils, and a polar end that dissolves in water •
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