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.

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