"The following reaction is the first step in the industrial synthesis of acetone and phenol. AIBN initiates radical reactions by breaking down upon heating to form two isobutyronitrile radicals and nitrogen gas. Using an isobutyronitrile radical to initiate the reaction, write a mechanism for the following process."

the process given

I was able to write a mechanism but I have to explain it to the class and I don't know how.

my solution

  • $\begingroup$ Count your electrons and your hydrogen atoms. Your product isn't quite right. $\endgroup$ – Zhe Apr 30 '17 at 1:47
  • $\begingroup$ en.wikipedia.org/wiki/Azobisisobutyronitrile $\endgroup$ – CoffeeIsLife Apr 30 '17 at 1:59
  • $\begingroup$ You still need to write a mechanism that explains how the radical leads to the product $\endgroup$ – CoffeeIsLife Apr 30 '17 at 2:02

AlBN is a sideway reagent (radical initiator). Cumene is the reactant and basicially reacts with radical O2(.) Since you create peroxide is a radicals mechanism (not neutral ALBN product that you wrote). Essentially is the Hock process mechanism. You should put the isopropyl cyanide radical in place of R, in the following mechanism and you are good. https://upload.wikimedia.org/wikipedia/commons/thumb/a/af/Hock-Phenol.png/751px-Hock-Phenol.png

Nevertheless, the first step is the creation of isopropyl cyanide radical. The mechanism is: https://upload.wikimedia.org/wikipedia/commons/thumb/5/56/Formation_of_Radicals_from_AIBN.png/1280px-Formation_of_Radicals_from_AIBN.png

DO NOT CONFUSE HALF-ARROW SYMBOL (which indicates movement of one electron) with DOUBLE (2 electron movement)


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