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Table of Contents

Carboxylic acids and their derivatives

Structure

Structure of derivatives

The acyl group

Nomenclature

Nomenclature

Nomenclature

Aromatic acids

Aldehydes - non-systematic names

IUPAC

Salts of carboxylic acids

Nomenclature of derivatives

Nomenclature of acyl halides

Nomenclature of anhydrides

Nomenclature of amides

Nomenclature of esters

Physical properties

Salts of carboxylic acids

Salts of carboxylic acids

Physical properties

Preparation of carboxylic acids

Oxidation of primary alcohols

Oxidation of arenes

Oxidation of arenes

Carbonation of Grignard reagents

Carbonation of Grignard reagents

Hydrolysis of nitriles

Preparation of nitriles - an SN2 reaction

Nomenclature of nitriles

Reactions - dissociation of carboxylic acids

Relative acidities

Acidity of carboxylic acids

Structure of carboxylate ions

Substituent effects

The acyl group

Reactivity of aldehydes and ketones

Reactivity of carboxylic acid derivatives

Reactivity of carboxylic acid derivatives

Reactivity of carboxylic acid derivatives

Base hydrolysis

Acid hydrolysis

Acid hydrolysis

SN2 v acyl substitution

Nucleophilic displacement - reactivity

Haloform reaction

Haloform reaction

Acid chlorides

Acid chlorides

Reactions of acyl halides - conversion into acids

Reactions of acyl halides - conversion into amides

Reactions of acyl halides - conversion into esters

Reactions of acyl halides - Friedel - Crafts’ acylation

Reactions of acyl halides with diorganocopper reagents

Reactions of acyl halides - the Rosemund reduction

Anhydrides - preparation of acetic anhydride

Preparation of other anhydrides

Hydrolysis of anhydrides

Aminolysis of anhydrides

Alcoholysis of anhydrides

Acylation

Preparation of esters

Preparation of esters

Preparation of esters

Reactions - base hydrolysis

Reactions - base hydrolysis

Predicted result for alkyl - oxygen bond breaking

Predicted result for acyl - oxygen bond breaking

Acyl - oxygen bond breaking - further proof using isotopic labels

However......?

Reactions - acid hydrolysis

Reactions - acid hydrolysis

Aminolysis of esters

Transesterification

Transesterification - acid catalysed

Transesterification - basic conditions

Transesterification - a preparation of polyvinyl alcohol

Reactions of ester with Grignard reagents

Preparation of amides

Preparation of amides from acyl chlorides

Reactions - acid catalysed hydrolysis

Reactions - base catalysed hydrolysis

Hofmann degradation

Reduction of acids

Reduction of esters

Hell-Volhard-Zelinsky reaction

a-Halocarboxylic acids

a-Halocarboxylic acids

Hell-Volhard-Zelinsky reaction

Spectroscopy

Phenols

Acidity of phenols

Acidity

Substituent effects

Substituent effects

Problems

CHEM 16X Home Page | Faculté Saint-Jean | University of Alberta | Chemistry Department

This page is maintained by Dr. Ed Blackburn (Ed.Blackburn@UAlberta.CA), course instructor.

Updated October 24, 2000