Ch. 14: Carboxylic Acids, Esters, Amines and Amides

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Ch. 14: Carboxylic Acids, Esters, Amines and Amides Chem 20 El Camino College

Carboxylic Acids, Esters, Amines

Naming Carboxylic Acids Name the longest carbon chain containing the carboxyl group. Use the suffix “oic acid” # the chain to give the carboxyl gp the lowest # Give the location and name of other substituents in alphabetical order, using numbers, hyphens, and commas between numbers

Un-Numbered 13.3

Name These propanoic acid methanoic acid (formic acid) ethanoic acid (acetic acid) 3-methylpentanoic acid

Benzoic Acid Benzoic acid is an important carboxylic acid

Carboxylic Acid Properties Carboxylic acids are extremely polar They have higher boiling pts than alcohols, ketones, and aldehydes of similar mass propanal, bp = 49 oC 1-propanol, bp = 97 oC acetic acid, bp = 118 oC Carboxylic acids with 4 C or less are water soluble

Figure 13.1

Un-Numbered 13.5

Esterification Carboxylic acids react with alcohols in the presence of heat and acid (H+) to form esters and water The OH comes off the carboxylic acid, and the H comes off the alcohol A new bond forms to make the ester

Draw the Ester Product

Naming Esters Name the the part that came from an alcohol (directly connected to an oxygen) first, use “yl” Then name the part that came from a carboxylic acid, use the “oate” suffix

Properties of Esters The scents of many flowers and fruits are esters

Types of Amines Amines are classified as primary (1o), secondary (2o), or tertiary (3o) In 1o amines, the N is attached to 1 carbon In 2o amines, the N is attached to 2 carbons In 3o amines, the N is attached to 3 carbons

Naming of Amines Name the carbon attachments in alphabetical order, use the word “amine” Use di- and tri- for identical substituents

Properties of Amines Amines tend to be bad-smelling compounds Amines are polar, they have relatively high boiling points Small amines are water soluble.

Un-Numbered 13.9

Un-Numbered 13.10

Un-Numbered 13.11

Amide Amides are derivative of carboxylic acids, in which a nitrogen group replaces the hydroxyl group. Amide is formed when a salt of carboxylic with ammonia or amine is heated; a molecule of water is eliminated. Amide can be hydrolyzed back to carboxylic acid and ammonium salt in acidic solution, or to a salt of carboxylic acid and ammonia or amine in basic solution.