In a reaction (as given in my textbook),

$$\ce{R-CH=CH2 + (CH3-CO)2O -> R-CH2=CH-COCH3}$$

an alkene reacts with acetic anhydride to give methyl alkenyl ketone.

I am not sure of how this proceeds, a search on google displays no links to any relevant matter, and I have not successfully found this reaction in any of the other books I possess.

According to me, it should have been an addition reaction (characteristic of alkenes) across the double bond. But this isn't the case here. So, what exactly is the reaction mechanism?


This is the Friedel-Crafts acylation reaction of alkene. Catalyzed by Lewis acid. Addition-elimination mechanism.


  • $\begingroup$ "The Friedel–Crafts reactions are a set of reactions developed by Charles Friedel and James Crafts in 1877 to attach substituents to an aromatic ring" - Wikipedia (read the whole Friedel Craft Reactions page), I am not as yet aware of any non-aromatic Friedel-Craft, any pointers or links would be much appreciated, thanks a lot.... $\endgroup$
    – Kaustubh
    May 24 '14 at 13:19
  • $\begingroup$ This was the only relevant article I found after a long search but that too gives just a 'page review' perhaps you could link something better thanks.. pubs.rsc.org/en/content/articlelanding/1972/cs/… $\endgroup$
    – Kaustubh
    May 24 '14 at 13:21
  • $\begingroup$ Here is the reference. Only first page is free. But you can see the introduction about that. pubs.rsc.org/en/content/articlelanding/1972/cs/… $\endgroup$
    – Coconut
    May 24 '14 at 15:16
  • $\begingroup$ Here is another link. It is full text. metzger.chemie.uni-oldenburg.de/download/83_engl.pdf $\endgroup$
    – Coconut
    May 24 '14 at 15:17

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