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While solving a few questions a came across a problem which asked me what would happen when sec-butyl ethanoate was heated.

I had never read about this reaction before and took to researching through a few of my textbooks, but could not find an explanation as to what would happen.

I also thought along the lines free radical formations and tried to make an attempt.

However according to the answer the reaction was a syn elimination and it would give a Hoffmann product. But I couldn't get any more information out of it.

But now I was stumped. So please help me out of you know anything about this.

compound

Edit:

After googling for sometime I came across a paper which said that this particular compound would decompose to give cis butene.

However I could not understand the reason for this. Here is where I saw it: https://pubs.acs.org/doi/pdf/10.1021/i360047a014

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    $\begingroup$ Depending upon the zeolite employed with sec-butyl acetate in your link, the cis/trans ratio varied between less and greater than one. cis-Butene is not the exclusive butene formed. $\endgroup$ – user55119 Jul 8 '20 at 22:01
  • $\begingroup$ @user55119 Okay! Noted. $\endgroup$ – Vamsi Krishna Jul 9 '20 at 5:49
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This is an example of a Thermal syn elimination. The Wikipedia article is a good place to start: here

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image from here

From ref 2

Unsymmetrical Acetate and xanthate esters yield a mixture of all the possible alkenes, but there is usually a predominance of the more highly substituted alkene.

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  • $\begingroup$ @NilayGhosh Found another image $\endgroup$ – Waylander Jul 8 '20 at 9:41

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