Carboxylic Acids - How Are Carboxyl Groups Reduced?

5 important questions on Carboxylic Acids - How Are Carboxyl Groups Reduced?

What is the most common reduction reagent for carboxylic acids?

Since the catalytic reduction (H2/M) will not work. Lithium aluminum hydride is mostly used.

What is the product of the reaction between a carboxylic acid and lithium aluminum hydride, LiAlH4?

The lithium aluminum hydride, LiAlH4, will First form a aluminum alkoxide which is than treated with water to form the primary alcohol. The reduction is usually carried out in an ether or tetrahydrofuoran.

Why are alkenes generally not affected by metal hydride-reducing reagents?

Metal hydride-reducing reagents act as hydride ion donors and function as nucleophiles. The carbon-carbon double bond of alkenes is usually not attact by nucleophiles.
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Using what reducing reagent, can an alkene functional group be reduced but without affecting the carboxyl group?

Catalytic hydrogenation will reduce the carbon-carbon double bond but not the carboxyl group.

Using what reducing reagent, can a carbonyl group be reduced but without affecting the carboxyl group?

It is possible to reduce an aldehyde or ketone carbonyl group selectively by using NaBH4 instead of LiAlH4, since the carboxyl group will not react with this reagent.

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