Pharmaceutical Organic Chemistry

Carboxylic acid Important chemical reactions

  • Carboxylic acid participates in several key chemical reactions due to the reactivity of the carboxyl group.
  • Here’s a summary of Carboxylic acid reactions:

Esterification chemical reactions of Carboxylic acid

  • Carboxylic acids react with alcohols to form esters and water, typically catalyzed by an acid like sulfuric acid.
  • Reaction: RCOOH + R’OH ⟶ RCOOR’ + H₂O
  • Example: Acetic Acid and Ethanol to Ethyl Acetate
    • CH₃COOH + CH₃CH₂OH CH₃COOCH₂CH₃ + H₂O

Acid-Base Reactions

  • Carboxylic acids neutralize bases to produce carboxylate salts and water.
  • Reaction: RCOOH + MOH ⟶ RCOOM + H₂O
  • Example: Acetic Acid and Sodium Hydroxide to Sodium Acetate
    • CH₃COOH + NaOH CH₃COONa + H₂O

Reduction to Alcohols

  • Carboxylic acids can be reduced to primary alcohols using reducing agents such as lithium aluminum hydride (LiAlH₄).
  • Reaction: RCOOH + 4[H] ⟶ RCH₂OH
  • Example: Acetic Acid to Ethanol
    • CH₃COOH + 4[H] CH₃CH₂OH

Decarboxylation

  • Heating carboxylic acids with a strong base results in the loss of carbon dioxide and formation of an alkane.
  • Reaction: RCOOH ⟶ RH + CO₂
  • Example: Propanoic Acid to Ethane
    • CH₃CH₂COOH CH₃CH₃ + CO₂

Formation of Acyl Halides

  • Carboxylic acids are converted to acyl halides using halogenating agents like thionyl chloride (SOCl₂).
  • Reaction: RCOOH + SOCl₂ ⟶ RCOCl + SO₂ + HCl
  • Example: Acetic Acid to Acetyl Chloride
    • CH₃COOH + SOCl₂ CH₃COCl + SO₂ + HCl

Formation of Amides

  • Carboxylic acids react with ammonia or amines to form amides, usually requiring heat or a dehydration agent.
  • Reaction: RCOOH + NH₃ ⟶ RCONH₂ + H₂O
  • Example: Acetic Acid to Acetamide
    • CH₃COOH + NH₃ CH₃CONH₂ + H₂O

These reactions highlight the diverse reactivity of carboxylic acids, making them key intermediates in various chemical syntheses.

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