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#Post#: 1194--------------------------------------------------
what is the product?
DIR By: Michel
Date: November 22, 2012, 3:34 am
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What is the product obtained by passing keten through acetic
acid
#Post#: 2202--------------------------------------------------
Re: what is the product?
DIR By: Potla
Date: February 26, 2013, 5:21 am
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Because (unstable) ketenes give acids on hydrolysis, I would
expect them to react with organic acids to give anhydrides.
R-CH=C=O + CH3COOH = CH3COOCOCH2R
A probable mechanism is through a neucleophilic attack by
CH3COO- at the unstable neucleophilic center (marked *) of
R-CH=C*=O, followed by the adjacent carbon grabbing a proton
probably from the solvent.
Please let me know if I am wrong. :)
#Post#: 2204--------------------------------------------------
Re: what is the product?
DIR By: Michel
Date: February 26, 2013, 5:39 am
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--- Quote from: Potla link ---
>
> Because (unstable) ketenes give acids on hydrolysis, I would
expect them to react with organic acids to give anhydrides.
> R-CH=C=O + CH3COOH = CH3COOCOCH2R
> A probable mechanism is through a neucleophilic attack by
CH3COO- at the unstable neucleophilic center (marked *) of
R-CH=C*=O, followed by the adjacent carbon grabbing a proton
probably from the solvent.
> Please let me know if I am wrong. :)
>
--- End Quote ---
you are correct. acetic anhydride is the expected product
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