I'm having trouble predicting the major product of the reaction of 1-(chloro(cyclohexyl)methyl)​cyclopropan-1-ol and silver ions:

Chemdraw image

I thought that in presence of $\ce{Ag^+}$, the three-membered ring would open forming a ketone with chlorine atom in the $\alpha$-position. Then I thought that there might also be some migration of the ketonic group to the ring, but I'm not sure.


1 Answer 1


A common test for haloalkanes (save fluoroalkanes) is reaction with $\ce{AgNO3}$, which initially yields the corresponding silver halide and a carbocation intermediate. The formation of the insoluble salt is the driving force for the reaction:

Carbocation formation

On a primary haloalkane this carbocation would be quenched with water, but adjacent to a three-membered ring this carbocation is primed for ring expansion. In addition to reducing ring strain, the resultant carbocation is even further stabilized by the oxygen atom:

Ring expansion

Deprotonation gives the final substituted cyclobutanone product.


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