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How to Convert Carboxylic Acids

Published in Organic Chemistry Reactions 2 mins read

Carboxylic acids are versatile organic compounds that can be transformed into various functional groups. One significant conversion, as highlighted in the provided reference, is their reduction to primary alcohols.

Converting Carboxylic Acids to Primary Alcohols

Carboxylic acids can be effectively converted into primary (1° alcohols) through a reduction reaction.

The key reagent for this conversion is Lithium aluminum hydride (LiAlH₄).

  • Reagent: Lithium aluminum hydride (LiAlH₄)
  • Product: Primary (1°) alcohol

It's important to note the strength of the reducing agent required for this transformation:

  • LiAlH₄ is strong enough to reduce carboxylic acids all the way to primary alcohols.
  • Sodium borohydride (NaBH₄) is NOT strong enough to perform this conversion on carboxylic acids (or esters).

This means that while LiAlH₄ can tackle the more stable carboxylic acid functional group, NaBH₄ typically only reduces less stable carbonyls like aldehydes and ketones.

Summary of the Conversion

Here's a breakdown of this specific conversion based on the reference:

  1. Starting Material: Carboxylic Acid (R-COOH)
  2. Reagent Used: Lithium aluminum hydride (LiAlH₄)
  3. Resulting Product: Primary Alcohol (R-CH₂OH)

Understanding the appropriate reducing agent is crucial for successfully converting carboxylic acids to primary alcohols in organic synthesis.

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