Hydrolysis of Aspirin Watch

StephAmanda
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#1
Report Thread starter 7 years ago
#1
As far as i am aware the ester group on an aspirin molecule is the only functional group which undergoes hydrolysis (base catalysed).

Usually ester hydrolysis converts an ester into a carboxylic acid, therefore i dont understand the how the mechanism takes place resulting in an OH group in salicylic acid.
Could anyone explain how this occurs?
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shengoc
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(Original post by StephAmanda)
As far as i am aware the ester group on an aspirin molecule is the only functional group which undergoes hydrolysis (base catalysed).

Usually ester hydrolysis converts an ester into a carboxylic acid, therefore i dont understand the how the mechanism takes place resulting in an OH group in salicylic acid.
Could anyone explain how this occurs?
what do you mean? this is normal base catalysed bimolecular acyl hydrolysis, Bac2 mechanism. lots of base catalysed ester hydrolysis undergo similar mechanism.
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Kyri
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I can see how you're getting confused. You're right that hydrolysis of esters give carboxylic acids but they also give alcohols. Ester hydrolysis is the reverse of esterification which you probably know requires alcohol + carboxylic acid. If you look at the way round the ester group is you can see the carboxylic acid part (the side with the carbonyl) is ethanoic acid and the alcohol part (the side with the C-O bond) is salicylic acid.
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illusionz
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Step one: Attack the ester carbonyl with OH-, resulting in nucleophilic addition-elimination, kicking out the best leaving group which in this cast is Ar-O- with Ar denoting the salicylic acid minus a proton on the alcohol group
Step two: The Ar-O- picks up a proton from a molecule of water, resulting in Ar-OH
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TheCount.
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This thread is like another language.
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