Acidic hydrolysis Watch

zblai1000
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CH3CH2C(OH)(CN)CH3 ---> CH3CH2C(OH)(COOH)CH3

How can this reaction be counted as an acidic or base hydrolysis? This is from a past year IAL Unit 4 paper and the MS said this method of conversion can be both acidic and base hydrolysis.
Now I'm actually confused on what does "hydrolysis" even mean, please help me out.

Thank you
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BobbJo
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(Original post by zblai1000)
CH3CH2C(OH)(CN)CH3 ---> CH3CH2C(OH)(COOH)CH3

How can this reaction be counted as an acidic or base hydrolysis? This is from a past year IAL Unit 4 paper and the MS said this method of conversion can be both acidic and base hydrolysis.
Now I'm actually confused on what does "hydrolysis" even mean, please help me out.

Thank you
It can be both acid and base hydrolysis. The conversion can be done by heating with mineral acid (but not concentrated sulfuric acid) or by heating with a base.

Hydrolysis is the cleavage of a covalent bond using water molecules. It is the reverse of condensation
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zblai1000
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Hydrolysis is the breaking of covalent bonds due to the attraction between water and atoms of the molecule right?
So am I right to say the N- of the CN is attracted to H+ of H2O? And then the OH- of water is attracted to C+ of CN and form COOH?
If yes, then my next question is where did the additional O from the COOH came from? If my explanation is right won't it be something like COH? (which is unlikely as C can form 4 bonds)

Please help me out, thank you very much.
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BobbJo
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(Original post by zblai1000)
Hydrolysis is the breaking of covalent bonds due to the attraction between water and atoms of the molecule right?
So am I right to say the N- of the CN is attracted to H+ of H2O? And then the OH- of water is attracted to C+ of CN and form COOH?
If yes, then my next question is where did the additional O from the COOH came from? If my explanation is right won't it be something like COH? (which is unlikely as C can form 4 bonds)

Please help me out, thank you very much.
That's not a very correct way to describe it.

Here is the mechanism of hydrolysis of nitriles

https://imgur.com/a/dCoIvuQ

It is nucleophilic addition-elimination
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zblai1000
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(Original post by BobbJo)
That's not a very correct way to describe it.

Here is the mechanism of hydrolysis of nitriles

https://imgur.com/a/dCoIvuQ

It is nucleophilic addition-elimin
Alright thank you for your help!
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