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Why couldn’t you use acid-base extraction to separate a ketone and an alcohol? why do we...

Why couldn’t you use acid-base extraction to separate a ketone and an alcohol?

why do we use column chromatography instead?

explain the benefits of both methods and why one is preferred over the other.

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Answer #1

Alcohols can consider as a weak acid, as it ha O-H bond. Hence it can form the salt with the strongest base (like NaOH), But ketone also has alfa hydrogen, hence it can act weak acid and gives enolate intermediate.Therefore both cannot separate using acid-base extraction. Whereas, in organic solvents( here, strong base not there), both in different polarity. Alcohol compound acts as polar than ketone. In TLC (Thin Layer Chromatography), two spots too far from one another, i.e Rf value is more. Therefore can separate using column chromatography.

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