Advantage of propanoyl chloride?

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phems
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#1
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#1
Hi,

Stuck with the following question:

Give one advantage of the use of propanoyl chloride instead of propanoic acid in the laboratory preparation of methyl propanoate from methanol.

Thanks
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illusionz
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#2
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#2
The acid anhydride gives the acid as a by product whereas the acid chloride gives HCl as a by product which is easier to seperate from the product you want.

The acid chloride is also more reactive and hence the reaction is faster.
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Theo_Batch
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#3
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#3
There’s no anhydride
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Theo_Batch
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#4
Report 3 months ago
#4
(Original post by phems)
Hi,

Stuck with the following question:

Give one advantage of the use of propanoyl chloride instead of propanoic acid in the laboratory preparation of methyl propanoate from methanol.

Thanks
Acyl chlorides are more reactive than carboxylic acids because they have a better leaving group attached to the carbon
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scimus63
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#5
Report 3 months ago
#5
using acid + alcohol to make ester is a poor way to do it, its an equilibrium reaction so you end up with a mixture of products and a poor yield of ester, using the acid chloride instead of the carboxylic acid, the reaction goes to completion, its not an equilibrium reaction.
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Son of the Sea
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#6
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#6
(Original post by Theo_Batch)
Acyl chlorides are more reactive than carboxylic acids because they have a better leaving group attached to the carbon
This thread is over 9 years old, I doubt the OP still needs the answer.
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j25_8
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#7
Report 3 months ago
#7
(Original post by Son of the Sea)
This thread is over 9 years old, I doubt the OP still needs the answer.
OP might not be the only one on tsr with that question though. If anybody needs an answer to that question, they can now come on tsr and find it
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