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

Chapter 17: Carboxylic Acids

Table of Contents:

• Structure

• Nomenclature

• Physical Properties

• Acidity

• Preparation of Carboxylic Acids

• Reduction

• Esterification

• Conversion to Acid Chlorides

• Decarboxylation

Structure

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

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

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