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Organic Chemistry by Brown, Iverson, Anslyn, Foote | Mayya's Study Guide | Chapter 17

Chapter 17: Carboxylic Acids


Table of Contents:


Structure


The functional group for carboxylic acid is COOH, also written as CO2H.


carboxylic acid structure
carboxylic acid structure

Nomenclature


  1. Find the longest continuous carbon chain containing COOH group and number starting from the carbon that contains the functional group.

  2. End the name in "oic acid".




Physical Properties

Carboxylic acids are polar, and have much higher boiling point than alcohols and aldehydes of similar mass. They are capable of hydrogen bonding and are very soluble in water



Acidity

  • Electron withdrawing groups (EWG) such as halogens make carboxylic acids more acidic.

  • The more EWG are on the carboxylic acid molecule and the closer they are to the COOH group, the more acidic it is.



Preparation of Carboxylic Acids


Grignard reagent with CO2 produces a carboxylic acid.


Product: Get rid of MgX and attach the carbon that had MgX to COOH.

Note: You get one EXTRA carbon going from the reactant to the product



Reactions of Carboxylic Acids


Reduction of Carboxylic Acid using lithium aluminum hydride

Reagent: LiAlH4

Product: Turn COOH into CH2OH


Reduction of carboxylic acid
Reduction of carboxylic acid

Fischer Esterification

Reagent: ROH, H+

Product: Turn OH on the carboxylic acid into OR (from the alcohol)


Fischer esterification
Fischer esterification

Formation of Methyl Esters Using Diazomethane

Reagent: CH2N2

Product: Turn OH on the carboxylic acid into OCH3


Formation of Methyl Esters Using Diazomethane
Formation of Methyl Esters Using Diazomethane

Mechanism

Formation of Methyl Esters Using Diazomethane mechanism
Formation of Methyl Esters Using Diazomethane mechanism

Conversion of Carboxylic Acids into Acid Chlorides

Reagent: SOCl2

Product: Turn OH on the COOH into Cl


Conversion of Carboxylic Acids into Acid Chlorides
Conversion of Carboxylic Acids into Acid Chlorides

Decarboxylation

Decarboxylation is a reaction where COOH group is lost completely from the molecule.

Decarboxylation only occurs if the molecule is beta-ketoacid. This means there is a carbonyl group (C=O) one carbon away from the COOH group.


how to predict the product of decarboxylation
how to predict the product of decarboxylation

Decarboxylation Mechanism


Decarboxylation Mechanism
Decarboxylation Mechanism

Carboxylic Reactions Cheat Sheet for Organic Chemistry : Mayya's Study Guide
Carboxylic Reactions Cheat Sheet for Organic Chemistry : Mayya's Study Guide
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