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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?

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?

Grade:12

1 Answers

Kaushik
28 Points
7 years ago

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.

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