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How to Prepare Carboxylic Acid?

Published in Organic Synthesis 3 mins read

Carboxylic acids can be prepared through several fundamental organic reactions, including the oxidation of alcohols and the hydrolysis of nitriles.

Here are two common methods for preparing carboxylic acids, based on established chemical principles:

Methods for Carboxylic Acid Synthesis

1. Oxidation of Primary Alcohols

One effective way to synthesize carboxylic acids is by oxidizing primary alcohols. This reaction typically requires a strong oxidizing agent.

  • Process: Primary alcohols are oxidized with a strong oxidizing agent, often in the presence of an acid.
  • Key Reagents: As noted in the reference, potassium dichromate (K₂Cr₂O₇) is a common oxidizing agent used for this purpose, carried out in the presence of an acid (like sulfuric acid). Other strong oxidants like potassium permanganate (KMnO₄) can also be used.
  • Reaction Type: This is a net oxidation reaction where the primary alcohol group (-CH₂OH) is converted first to an aldehyde, and then further oxidized to a carboxylic acid (-COOH).
  • Example: The oxidation of ethanol (a primary alcohol) to ethanoic acid (acetic acid) using potassium dichromate and acid.
R-CH₂OH + [Oxidizing Agent/Acid] → R-COOH

2. Hydrolysis of Nitriles

Another reliable method for preparing carboxylic acids involves the hydrolysis of nitriles.

  • Process: A nitrile compound is reacted with water under acidic or basic conditions.
  • Key Reagents: The reference specifically mentions the reaction where a nitrile is reacted with water in the presence of an acid. Acidic hydrolysis is commonly performed by heating the nitrile with a dilute mineral acid (like HCl or H₂SO₄). Basic hydrolysis using a base like NaOH followed by acidification is also possible.
  • Reaction Type: This is a hydrolysis reaction where the triple bond of the nitrile group (-C≡N) is cleaved with the addition of water across the bond, ultimately yielding a carboxylic acid and ammonia (or ammonium salt under acidic conditions).
  • Example: The hydrolysis of ethanenitrile (acetonitrile) to ethanoic acid (acetic acid) using water and acid.
R-C≡N + 2 H₂O + [Acid] → R-COOH + NH₄⁺

These methods are foundational in organic synthesis for accessing carboxylic acids from simpler precursors.

Summary of Methods

Method Starting Material Key Reagents Functional Group Change
Oxidation of Primary Alcohols Primary Alcohol Potassium dichromate, Acid -CH₂OH → -COOH
Hydrolysis of Nitriles Nitrile Water, Acid -C≡N → -COOH

Understanding these reactions is crucial for planning synthetic routes to carboxylic acids in organic chemistry.

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