In my textbook Organic Chemistry, 2nd edition by Clayden, on pg. 464 it states the addition of $\ce{NO2-,HCl}$ to cyclohexanone to 2-nitrosocyclohexanone, which hydrolyses to 1,2-cyclohexadione. Why does the Beckmann rearrangement not occur in 2-nitrosocyclohexanone instead?
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2$\begingroup$ First, reaction conditions are important here. Second, do no assume that the nitroso is the same as the oxime. $\endgroup$– ZheCommented May 14, 2018 at 18:34
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$\begingroup$ Because the oxime hydrolysis is faster than the Beckmann rearrangement (after the nitroso has isomerised) $\endgroup$– BeerhunterCommented May 20, 2018 at 23:17
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