preparation-of-alcohols

Question

How is it that Palladium hydride(H2) can reduce an ester into an alcohol but not a carboxylic acid into an ester(even if both carboxylic acid and ester have almost similar structure,except the hydrogen in carboxylic acid)? I know we need LiAlH4 to reduce carboxylic acid into alcohol. But I just want to know why Ester with Palladium H2 makes alcohol but carboxylic acid with Palladium H2 does not make alcohol even if both are almost similar?

Kaushik · Accepted Answer

Carboxylic acids possess acidic hydrogen. When we use a reducing agent, the next effect is a hydride donation.Since the acid possesses acidic hydrogen(H+) and the reducing agent donates hydride(H-),they to combine to give hydrogen gas.Hence H2/Pd is not used.However, a stronger reducing agent like LiAlH4 is used.This is not so in an ester as they possess no acidic hydrogen.

Organic Chemistry> preparation-of-alcohols...

Add Gupta , 12 Years ago

Kaushik

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Organic Chemistry> preparation-of-alcohols...

Add Gupta , 12 Years ago

Kaushik

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