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Topic: Need help understanding this reaction mechanism  (Read 3125 times)

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Offline hello110786

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Need help understanding this reaction mechanism
« on: March 04, 2017, 03:27:07 PM »
Hello, i would appreciate if someone can tell me what is is going on in each step of this reaction. if you can please include the type of reaction taking place at each step etc. such as nucleophilic substitution etc. movement of electrons etc...

the reaction is attached

Offline brinco23

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Re: Need help understanding this reaction mechanism
« Reply #1 on: March 05, 2017, 10:56:19 AM »
I shall try to help you, however my technical English is quite bad, so bare with me
First step: Nucleophilic attack by the alcohol group on acyl chloride. acyl chlorides are quite reactive, so that is why the reaction takes place.
Second Step: Chlorine is a good leaving group, because it`s conjugated acid (HCl) has a small pKa. Therefore the carbonyl (C double bonded with O) is favoured and thus the Cl is expelled.
The pKa thing is more of a helper in determining leaving group ability rather than an explanation of why it happens.
Hope I helped!

Offline AWK

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Re: Need help understanding this reaction mechanism
« Reply #2 on: March 05, 2017, 11:06:09 AM »
This is rather odd reaction. Oxalyl chloride (if this is correct formula) forms oxalate diesters (with alcohols, phenols. As an acceptor of acid usually pyridine is used.

You start from oxalyl chloride and obtain ester of acetic acid?
AWK

Offline dshipp17

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Re: Need help understanding this reaction mechanism
« Reply #3 on: March 05, 2017, 03:33:13 PM »
This reaction is organic chemistry related. It's showing the steps for creating an aldehyde or ketone in a systematic fashion; from a preliminary inspection, this looks like a ketone; the reaction is taking place on the functional groups. Sorry, that's an ester and this is an esterification reaction (or ether; confirming, actually, that is an ester as first claimed).

Offline Dan

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Re: Need help understanding this reaction mechanism
« Reply #4 on: March 06, 2017, 01:56:16 AM »
You have drawn a phenol reacting with oxalyl chloride to give a formate ester (seems unlikely), then drawn conversion of a formate ester into an acetate ester using only H+ (impossible). There are mistakes in the scheme which need to be corrected.
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Offline Babcock_Hall

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Re: Need help understanding this reaction mechanism
« Reply #5 on: March 07, 2017, 09:24:29 AM »
In addition it is a Forum Rule (see red link) that you must show your attempt or your thoughts before we can help you.

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