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How are carboxylic acids reduced to primary alcohols?
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carboxylic acid
Alcohols may be oxidized to give aldehydes, ketones, and carboxylic acids. The oxidation of organic compounds generally increases the number of bonds from carbon to oxygen, and it may decrease the number of bonds to hydrogen.
Carboxylic acids are more difficult to reduce than aldehydes or ketones, but they can be converted into primary alcohols (RCOOH → RCH₂OH) using specific chemical reducing agents.1
The most important agents used for this reduction are:
- Lithium aluminum hydride (LiAlH₄): A powerful reducing agent commonly used to convert carboxylic acids directly into primary alcohols.123
- Borane (BH₃): Another effective agent for achieving this transformation.1
While carboxylic acids cannot be directly reduced to aldehydes using general methods, they can be converted to primary alcohols through these reagents. Alternatively, one may indirectly produce an aldehyde by first converting the carboxylic acid into an acyl chloride, which can then be reduced.1