CHAPTER 20CARBOXYLIC ACIDS AND THEIR

DERIVATIVES

CH 20.1TOPIC: INTRODUCTION TO

CARBOXYLIC ACIDS

INTRODUCTION TO CARBOXYLIC ACIDS

• CARBOXYLIC ACIDS : COMPOUNDS WITH –COOH GROUP

• ARE ABUNDANT IN NATURE

• FOUND IN A WIDE VARIETY OF SYNTHETIC

PHARMACEUTICALS

INTRODUCTION TO CARBOXYLIC ACIDS

• CARBOXYLIC ACIDS FOUND IN A WIDE RANGE OF

PHARMACEUTICALS THAT ARE USED TO TREAT VARIETY OF

CONDITIONS

• THE US PRODUCES OVER 2.5 MILLION TONS OF ACETIC ACID PER YEAR, WHICH IS

PRIMARILY USED TO PRODUCE VINYL ACETATE

INTRODUCTION TO CARBOXYLIC ACIDS

• VINYL ACETATE IS USED IN PAINTS AND ADHESIVES

• CARBOXYLIC ACID DERIVATIVES SUCH AS VINYL ACETATE ARE VERY COMMON

AND PLAY A CENTRAL ROLE IN ORGANIC CHEMISTRY

CH 20.2TOPIC: NOMENCLATURE OF

CARBOXYLIC ACIDS

MONOCARBOXYLIC ACIDS

• MONOCARBOXYLIC ACIDS: COMPOUND CONTAINING ONE CARBOXYLIC

ACID GROUP

• MONOCARBOXYLIC ACIDS ARE NAMED WITH THE SUFFIX “OIC ACID”

MONOCARBOXYLIC ACIDS

• PARENT IS THE LONGEST CHAIN THAT INCLUDES THE CARBON ATOM OF THE

CARBOXYLIC ACID GROUP

• THE CARBON OF THE CARBOXYLIC ACID MOIETY IS ASSIGNED LOCANT

POSITION 1

• WHEN THE CARBOXYLIC ACID GROUP IS ATTACHED TO A RING, IT IS NAMED

AS AN ALKANE CARBOXYLIC ACID

EXAMPLE:

MONOCARBOXYLIC ACIDS

• THERE ARE ALSO MANY COMMON NAMES FOR CARBOXYLIC ACIDS

EXAMPLES:

DIACIDS• DIACIDS: COMPOUNDS CONTAINING TWO CARBOXYLIC ACID GROUPS

• DICARBOXYLIC ACIDS ARE NAMED WITH THE SUFFIX “DIOIC ACID”

• SOME DICARBOXYLIC ACIDS HAVE COMMON NAMES ACCEPTED BY IUPAC

• LET’S TRY HMWK #1-3

CH 20.6TOPIC: INTRODUCTION TO

CARBOXYLIC ACID DERIVATIVES

NAMING ACID HALIDES

• TO NAME AN ACID HALIDE, REPLACE - IC ACID WITH - YL HALIDE

NAMING ACID HALIDES

• IF AN ACID HALIDE GROUP IS CONNECTED TO A RING, THE SUFFIX,

“CARBOXYLIC ACID” CAN BE REPLACED WITH “CARBONYL HALIDE”

NAMING ANHYDRIDES

• ACID ANHYDRIDES ARE NAMED BY REPLACING “ACID” WITH “ANHYDRIDE”

NAMING ANHYDRIDES

• UNSYMMETRICAL ANHYDRIDES ARE PREPARED FROM TWO

DIFFERENT CARBOXYLIC ACIDS

• ASYMMETRICAL ANHYDRIDES ARE NAMED BY LISTING THE ACIDS

ALPHABETICALLY, FOLLOWED BY “ANHYDRIDE”

Naming Esters• ESTERS ARE NAMED BY NAMING THE ALKYL GROUP ATTACHED TO

THE OXYGEN ATOM FOLLOWED BY THE CARBOXYLIC ACID’S NAME

WITH THE SUFFIX –ATE

• THE SUFFIX “IC ACID” IS REPLACED WITH “ATE”

Naming Esters

• ESTERS ARE NAMED BY NAMING THE ALKYL GROUP ATTACHED TO

THE OXYGEN FOLLOWED BY THE CARBOXYLIC ACID’S NAME WITH

THE SUFFIX –ATE

• SAME RULES APPLY IF THE ESTER IS CONNECTED TO A RING

EXAMPLE:

NAMING AMIDES

• AMIDES ARE NAMED BY REPLACING THE SUFFIX -IC ACID OR -OIC

ACID WITH -AMIDE

NAMING AMIDES

• AMIDES ARE NAMED BY REPLACING THE SUFFIX -IC ACID OR -OIC

ACID WITH –AMIDE

• IF AMIDE GROUP IS CONNECTED TO A RING, “CARBOXYLIC ACID”

IS REPLACED WITH “CARBOXAMIDE”

NAMING AMIDES

• IF THE NITROGEN ATOM OF THE AMIDE GROUP BEARS ALKYL

SUBSTITUENTS, THEIR NAMES ARE PLACED AT THE BEGINNING OF

THE NAME WITH N AS THEIR LOCANT

NAMING NITRILES

• NITRILES ARE NAMED BY REPLACING THE SUFFIX -IC ACID OR -OIC

ACID WITH –ONITRILE

• LET’S TRY HMWK #12-13