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Topic: What kind of reaction is it?  (Read 3130 times)

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Offline wojtass129

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What kind of reaction is it?
« on: March 16, 2016, 08:57:30 AM »
http://imgur.com/tqRoxQD
The "A" compound is a product of this reaction, but I don't know what kind of reaction is it. I figured out that epoxide ring will open due to Na+ EtO- making ether with OH- group in it, but still I don't know how A product is formed. Any hint will be really appreciated  :)
« Last Edit: March 16, 2016, 09:24:49 AM by Arkcon »
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Offline mjc123

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Re: What kind of reaction is it?
« Reply #1 on: March 16, 2016, 09:21:24 AM »
What else can EtO- do?
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Offline wojtass129

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Re: What kind of reaction is it?
« Reply #2 on: March 16, 2016, 10:12:23 AM »
It takes part in many condensation reactions, but this kind of reaction doesn't make sense if there is epoxide as one of the substrates
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Offline mjc123

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Re: What kind of reaction is it?
« Reply #3 on: March 16, 2016, 11:42:20 AM »
Think back a stage. What role can EtO- perform, other than that of a nucleophile?
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Offline wojtass129

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Re: What kind of reaction is it?
« Reply #4 on: March 16, 2016, 12:54:30 PM »
Is it about ester hydrolysis under alkaline conditions? It gives me then carboxylic acid and epoxide, which I still don't know how they react with each other
Edit: Is this reagents will proceed through Claisen rearrangement?
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Offline Dan

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Re: What kind of reaction is it?
« Reply #5 on: March 16, 2016, 01:03:19 PM »
Quote from: wojtass129 on March 16, 2016, 12:54:30 PM
Is it about ester hydrolysis under alkaline conditions? It gives me then carboxylic acid and epoxide, which I still don't know how they react with each other
Edit: Is this reagents will proceed through Claisen rearrangement?

No, there's no water, so no hydrolysis.

Other than acting a nucleophile, what can ethoxide do?
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Offline wojtass129

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Re: What kind of reaction is it?
« Reply #6 on: March 16, 2016, 03:03:49 PM »
I have no idea what you mean. Tbh I'm a high school student and I posted in Undergraduate General Chemistry Forum as it's question from chemistry contest (it ended). I'm struggling with this reaction for 2 months and at this point I'm just begging for answer. I've been searching in books and didn't find anything useful, asking my chemistry teachers but they don't know mechanism either  :-\
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Offline AWK

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Re: What kind of reaction is it?
« Reply #7 on: March 16, 2016, 03:49:54 PM »
Look patiently in English wikipedia under ethylene oxide.
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