Carboxylic Acids, Esters, and Other Acid Derivatives PDF

# Carboxylic Acids, Esters, and Other Acid Derivatives ## Chapter Outline - Structure of Carboxylic Acids and Their Derivatives - IUPAC Nomenclature for Carboxylic Acids - Common Names for Carboxylic Acids - Polyfunctional Carboxylic Acids - Physical Properties of Carboxylic Acids - Preparation of...

# Carboxylic Acids, Esters, and Other Acid Derivatives ## Chapter Outline - Structure of Carboxylic Acids and Their Derivatives - IUPAC Nomenclature for Carboxylic Acids - Common Names for Carboxylic Acids - Polyfunctional Carboxylic Acids - Physical Properties of Carboxylic Acids - Preparation of Carboxylic Acids - Acidity of Carboxylic Acids - Carboxylic Acid Salts - Structure of Esters - Preparation of Esters - Nomenclature for Esters - Selected Common Esters - Isomerism for Carboxylic Acids and Esters - Physical Properties of Esters - Chemical Reactions of Esters - Sulfur Analogs of Esters - Polyesters - Acid Chlorides and Acid Anhydrides - Esters and Anhydrides of Inorganic Acids - Nonprescription Pain Relievers Derived from Propanoic Acid - Carboxylic Acids and Skin Care - Aspirin - Nitroglycerin: An Inorganic Triester ## 16.1 Structure of Carboxylic Acids and Their Derivatives - A carboxylic acid is an organic compound whose functional group is the carboxyl group. - A carboxyl group is a carbonyl group (C=O) that has a hydroxyl group (-OH) bonded to the carbonyl carbon atom. - Abbreviated linear designations for the carboxyl group are -COOH and -CO₂H. ## 16.2 IUPAC Nomenclature for Carboxylic Acids - A monocarboxylic acid is a carboxylic acid in which one carboxyl group is present. - IUPAC rules for naming monocarboxylic acids include: - Select the parent carbon chain as the longest carbon chain that includes the carbon atom of the carboxyl group. - Name the parent chain by changing the -e ending of the corresponding alkane to -oic acid. - Number the parent chain by assigning the number 1 to the carboxyl carbon atom, but omit the number for the name. - Determine the identity and location of any substituents in the usual manner, and append this information to the front of the parent chain name. - If the carbonyl group is bonded to a carbon ring, name the ring and add the words carboxylic acid. The carbon bearing the carboxyl group is always carbon 1. Locate any other substituents in the usual manner. ## 16.3 Common Names for Carboxylic Acids - The use of common names is more prevalent for carboxylic acids than for any other family of organic compounds. - Common names for carboxylic acids are usually derived from a Latin or Greek word that is related to a source for the acid. ### Monocarboxylic Acids - The common name of a monocarboxylic acid is formed by taking the Latin or Greek root name for the specific number of carbon atoms and appending the suffix -ic acid. ### Dicarboxylic Acids - A dicarboxylic acid is a carboxylic acid that contains two carboxyl groups, one at each end of a carbon chain. - Saturated acids of this type are named by appending the suffix -dioic acid to the corresponding alkane name (the -e is retained to facilitate pronunciation). ### Aromatic Carboxylic Acids - The simplest aromatic carboxylic acid is called benzoic acid. - Other simple aromatic acids are named as derivatives of benzoic acid. ## 16.4 Polyfunctional Carboxylic Acids - A polyfunctional carboxylic acid is a carboxylic acid that contains one or more additional functional groups besides one or more carboxyl groups. - Important types of polyfunctional carboxylic acids include unsaturated acids, hydroxy acids, and keto acids. ## 16.5 Physical Properties of Carboxylic Acids - Carboxylic acids are the most polar organic compounds. - The result is very high melting and boiling points for carboxylic acids, the highest of any type of organic compound. ## 16.6 Preparation of Carboxylic Acids - Oxidation of primary alcohols or aldehydes, using an oxidizing agent such as CrO3 or K₂Cr₂O₇ produces carboxylic acids. - Aromatic acids can be prepared by oxidizing a carbon side chain (alkyl group) on a benzene derivative. ## 16.7 Acidity of Carboxylic Acids - Carboxylic acids are acidic. - When placed in water, hydrogen ion transfer (proton transfer) occurs to produce hydronium ion (the acidic species in water) and carboxylate ion. ## 16.8 Carboxylic Acid Salts - A carboxylic acid salt is an ionic compound in which the negative ion is a carboxylate ion. - Carboxylic acid salts are named similarly to other ionic compounds. ## 16.9 Structure of Esters - An ester is a carboxylic acid derivative in which the -OH portion of the carboxyl group has been replaced with an -OR group. - The ester functional group is thus C-O-R ## 16.10 Preparation of Esters - Esters are produced through esterification. - An esterification reaction is the reaction of a carboxylic acid with an alcohol (or phenol) to produce an ester. - A strong acid catalyst (generally H₂SO₄) is needed for esterification.