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.



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

  • 2
    $\begingroup$ 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, 2020 at 22:01
  • $\begingroup$ @user55119 Okay! Noted. $\endgroup$ Jul 9, 2020 at 5:49

1 Answer 1


This is an example of a Thermal syn elimination. The Wikipedia article is a good place to start: here

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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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