Third Trimester
Lesson 6: Carboxylic Acid and Derivatives Review Session and Practice Problems
Review of Key Concepts
Carboxylic Acids:
Structure and Properties: Understand the functional group -COOH and its acidic nature.
Common Reactions: Review esterification, reduction, and formation of derivatives (e.g., esters, amides).
Carboxylic Acid Derivatives:
Esters: Learn their formation from carboxylic acids and alcohols, and their reactions, such as hydrolysis and Grignard reactions.
Amides: Understand their synthesis from carboxylic acids or esters and their reduced basicity due to resonance.
Anhydrides: Review their formation from carboxylic acids and their reactions, such as hydrolysis.
Acyl Chlorides: Discuss their synthesis and high reactivity leading to various transformations (e.g., to esters, amides).
Intramolecular Reactions
Lactonization: Formation of cyclic esters from hydroxy acids.
Lactamization: Formation of cyclic amides from amino acids.
Grignard Reagents
Formation: Understand the preparation of Grignard reagents (RMgX) and their nucleophilic nature.
Reactions with Carbonyl Compounds: Focus on the addition to esters, leading to tertiary alcohols after hydrolysis.
Reductions Using Lithium Aluminum Hydride (LiAlH4) and Triethyl Borohydride (LiAl(OR)3)
LiAlH4: Strong reducing agent that reduces esters, amides, and carboxylic acids to primary alcohols or amines.
LiAl(OR)3: Milder reducing agent for selective reductions, particularly of esters to alcohols.
Hofmann Rearrangement Mechanism
Overview: Conversion of primary amides to primary amines with loss of one carbon atom.
Mechanism: Detailed steps involving the formation of bromamide intermediate, nitrene intermediate, rearrangement, and hydrolysis.
Practice Problems
Problem-Solving: Apply concepts through targeted practice problems covering the reactions and mechanisms reviewed.
Reaction Identification: Identify products of reactions involving carboxylic acids and their derivatives.
Mechanism Elucidation: Draw detailed mechanisms for reactions such as esterification, Grignard additions, reductions, and the Hofmann rearrangement.
Synthesis Pathways: Design multi-step synthesis pathways using carboxylic acid derivatives.