1 Chapter 16 Carboxylic Acids and Esters 16.1 Carboxylic Acids Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 2 A carboxylic acid Contains a carboxyl group, which is a carbonyl group (C=O) attached to a hydroxyl group (—OH). Has the carboxyl group on carbon 1. carbonyl group O || CH3 — C—OH hydroxyl group or CH3COOH carboxyl group Carboxylic Acids 3 Models of Carboxylic Acids The three-dimensional models show the geometry of atoms in carboxylic acid molecules. Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 4 The IUPAC names of carboxylic acids Replace the -e in the alkane name with -oic acid. CH4 methane HCOOH methanoic acid CH3—CH3 ethane CH3—COOH ethanoic acid Number substituents from the carboxyl carbon 1. CH3 O | ║ CH3—CH—CH2—C—OH 4 3 2 1 3-methylbutanoic acid IUPAC Names 5 The common names of simple carboxylic acids Are formic acid (1C), acetic acid (2C), propionic acid (3C), and butyric acid (4C). HCOOH formic acid CH3—COOH acetic acid Locate substituents using α, β, γ for the carbon atoms adjacent to the carboxyl carbon. CH3 γ β| α CH3—CH—CH2—COOH 3-methylbutanoic acid (β-methylbutryic acid) Common Names 6 Alpha Hydroxy Acids Alpha hydroxy acids (AHAs) Occur naturally in fruit, milk, and sugarcane. Are used in skin care products. Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 7 Names and Sources of Some Carboxylic Acids TABLE 16.1 Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 8 Common Carboxylic Acids Methanoic acid (formic acid) O ║ H─C─OH ethanoic acid (acetic acid) O ║ CH3─C─OH Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 9 Aromatic Carboxylic Acids Benzoic acid Is the aromatic carboxylic acid. Locates substituents by assigning 1 to the carbon attached to the carboxyl group. Has common names that assign prefixes ortho, meta, and para for 2 substituents. ortho 1, 2 location meta 1, 3 location para 1, 4 location 10 Aromatic Carboxylic Acids OHC O OHC O OHC O Cl NH 2 benzoic acid 3-chlorobenzoic acid 4-aminobenzoic acid m-chlorobenzoic acid p-aminobenzoic acid [...]... acid 17 Chapter 16 Carboxylic Acids and Esters 16.2 Properties of Carboxylic Acids Copyright © 2007 by Pearson Education, Inc Publishing as Benjamin Cummings 18 Polarity of Carboxylic Acids Carboxylic acids Are strongly polar Have two polar groups: hydroxyl (−OH) and carbonyl (C=O) δ O ║δ + δ - + δ CH3CO H 19 Boiling Points of Carboxylic Acids The boiling points of carboxylic acids Are higher... in Water Carboxylic acids Water molecules Form hydrogen bonds with many water molecules With 1-4 carbon atoms are very soluble in water Copyright © 2007 by Pearson Education, Inc Publishing as Benjamin Cummings 22 Boiling Points and Solubility TABLE 16.2 Copyright © 2007 by Pearson Education, Inc Publishing as Benjamin Cummings 23 Acidity of Carboxylic Acids Carboxylic acids Are weak acids Ionize... Cummings 24 Acid Dissociation Constants Carboxylic acids TABLE 16.3 Have small Ka values Exist mostly as molecules and a few ions in aqueous solutions 25 Neutralization of Carboxylic Acids Carboxylic acid salts Are a product of the neutralization of a carboxylic acid with a strong base – + CH3—COOH + NaOH CH3—COO Na + H2O acetic acid sodium acetate (carboxylic acid salt) Are used as preservatives... Chapter 16 Carboxylic Acids and Esters 16.3 Esters 16.4 Naming Esters Copyright © 2007 by Pearson Education, Inc Publishing as Benjamin Cummings 29 Esters In an ester, The H in the carboxyl group is replaced with an alkyl group O || CH3 — C—O—CH3 ester group Copyright © 2007 by Pearson Education, Inc Publishing as Benjamin Cummings 30 Esterification Esterification is The reaction of a carboxylic. .. CH3─CH2─COOH propanoic acid (propionic acid) CH3 | B CH3─CH─CH2─COOH 3-methylbutanoic acid (β-methylbutyric acid) O C 3-bromobenzoic acid C OH (m-bromobenzoic acid) Br 14 Preparation of Carboxylic Acids Carboxylic acids can be prepared by oxidizing primary alcohols or aldehydes The oxidation of ethanol produces ethanoic acid (acetic acid) OH | [O] CH3—CH2 O || [O] CH3—C—H ethanol ethanal (ethyl alcohol)... reduce inflammation C OH O Is an ester of salicylic acid and acetic acid Oil of wintergreen O O C CH3 Is used to soothe sore muscles Is an ester of salicylic acid and methanol O C O CH3 OH 35 Esters in Plants Esters give flowers and TABLE 16.4 fruits their pleasant fragrances and flavors 36 Copyright © 2007 by Pearson Education, Inc Publishing as Benjamin Cummings ... Solution Write the equation for the reaction of propanoic acid and methanol in the presence of an acid catalyst O || CH3—CH2—C—OH + H—O—CH3 propanoic acid O H + methanol || CH3—CH2—C—O—CH3 + H2O 33 Naming Esters The name of an ester contains the names of The alkyl group from the alcohol The carbon chain from the acid with –ate ending from alcohol from acid O methyl || CH3— O—C —CH3 ethanoate (acetate) . 1 Chapter 16 Carboxylic Acids and Esters 16.1 Carboxylic Acids Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 2 A carboxylic. of Carboxylic Acids Chapter 16 Carboxylic Acids and Esters Copyright © 2007 by Pearson Education, Inc. Publishing as Benjamin Cummings 19 Polarity of Carboxylic