Chapter 13: Carboxylic Acids and Acid Derivatives

Ch. 13 – Carboxylic Acids and Acid Derivatives

DAT Organic Chemistry Outline

Chapter 13: Carboxylic Acids and Acid Derivatives Lesson 13.1 – Interconversion of Acid Derivatives Nucleophilic Acyl Substitution

Reactivity = acid chloride > anhydrides > esters/carboxylic acids > amides > carboxylates) Lesson 13.2 – Physical Properties of Carboxylic Acids • Carboxylic acids have a higher boiling point due to dimerization and H-bonding Lesson 13.3 – Fischer Esterification and Saponification Fischer Esterification

Saponification

© DAT Bootcamp

1 of 3|Page

Ch. 13 – Carboxylic Acids and Acid Derivatives

DAT Organic Chemistry Outline

Lesson 13.4 – Hydride Reductions of Acid Derivatives NaBH4 reduces ketones, aldehydes, and acid chlorides, and acid anhydrides

LiAlH4 reduces ketones, aldehydes, acid chlorides, esters, carboxylic acids, amides, etc.

*amides are reduced to an amine Hoffman Rearrangement

•

Turns amides into amines and also removes 1 carbon

© DAT Bootcamp

2 of 3|Page

Ch. 13 – Carboxylic Acids and Acid Derivatives

DAT Organic Chemistry Outline

Lesson 13.5 – Mild Hydride Reductions DIBAL-H reduces esters to aldehydes

DIBAL-H LTBA (Lithium tri-t-butoxy aluminum hydride) reduces acid chlorides to aldehydes

LTBA

© DAT Bootcamp

3 of 3|Page