(Solved) Explain why acetyl chloride reacts faster with water than acetic anhydride.

FionaSupernova

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9 years ago

Explain why acetyl chloride reacts faster with water than acetic anhydride.

Is this because of their leaving groups and resonance stabilization? Or, are there unique characteristics in water that make acetyl chloride more reactive to it than acetic anhydride?

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padre

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rsb

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9 years ago

AcOCl (Acetyl Chloride) Because the bond between Cl and the electron withdrawn C is very weak Cl atom is easily reduced by H-OH's H+ to HCl while the carbon atom of the AcO=C- is easily oxidated by OH- forming AcOH.

AcOAc (Acetic Anhydride) is a dequenching agent this means he is very prone to hydration. Because he is an ether of two Acetyl groups the ether bonds are very weak. When this molecule is met with an Acidic Hydrogen the Basic O traps that Hydrogen AcOHAc and that ether bond breaks and an Ac group is liberated to find an O or N.

EtOAC (Ethyl Acetate) This is a quite stable molecule so he wont react with H-OH as AcNH2 (Acetamide) is.

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wizarddim

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9 years ago

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Cl atom is easily reduced by H-OH's H+ to HCl while the carbon atom of the AcO=C- is easily oxidated by OH- forming AcOH.

Acid base reactions are not redox reactions. C stays at same oxidation state (the acid oxidation state) and Cl also stays at same oxidation state (the chloride oxidation state)

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