Carboxylic Acids

1
Carboxylic Acids

• Nomenclature
• Properties
• Preparation reactions
• Typical reactions
• Spectroscopy

2
Nomenclature

• Carboxylic acids
• IUPAC
• Common
• Acid derivatives
• IUPAC
• Common

3
RCOOH Preparation Reactions

• Oxidation of Primary Alcohols
• Oxidation of Aldehydes
• Oxidation of Substituted Aromatics
• Carbonation of Grignard reagents
• Hydrolysis of Acid derivatives and Nitriles
• Haloform reaction
• Periodic acid Cleavage of Vicinal Dials/Diketones
• Oxidative Cleavage of Alkenes/Alkynes

4
Carboxylic Acids via Oxidation

• From Primary Alcohols
• From Aldehydes
• From Substituted Aromatics

5
Carbonation of Grignard Reagents
6
Hydrolysis of Acid Derivatives and Nitriles
7
Haloform Reaction

• Cleavage of methyl carbinols
• Cleavage of methyl carbonyls

8
Periodic Acid Cleavage of Vicinal Dials/Diketones
9
Oxidative Cleavage Reactions

• Alkene Cleavage
• Hot Potassium Permanganate
• Alkyne Cleavage
• Hot Potassium Permanganate
• Ozonolysis

10
Typical RCOOH reactions

• Conversion to carboxylate salts
• Conversion to acid halides
• Conversion to esters
• Conversion to amides
• Conversion to anhydrides
• Reduction to alcohols
• Decarboxylation

11
Carboxylates from Carboxylic Acids

• Reaction with Active Metals
• Reaction with Strong Base
• Reaction with Weak Base

12
Acid Chlorides from RCOOH

• Reaction with Thionyl Chloride
• Reaction with Phosphorus Trichloride
• Reaction with Phosphorus Pentachloride

13
Ester Formation

• From Carboxylic Acids
• with ROH via mineral acid catalysis
• via the use of diazomethane
• From Acid Chlorides
• From Acid Anhydrides

14
Amide Formation

• Direct Conversion of Acids to Amides
• From Acid Chlorides
• From Acid Anhydrides
• From Esters

15
Acid Anhydride Formation

• Via Dehydration of Carboxylic Acids
• Via Reaction of RCOCl with RCOOH
• Via Reaction of RCOCl with RCOONa

16
Formation of Cyclic Anhydrides
17
Reduction of Carboxylic Acids

• Lithium Aluminum Hydride reduction
• Diborane reduction

18
Decarboxylation of RCOOH

• Thermolysis of beta-diacids
• Thermolysis of beta-keto acids

19
Spectroscopy

• Infrared
• Pmr
• Cmr