Predict the major product of the following reaction with mechanism [closed]








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[![enter image description here](https://i.stack.imgur.com/BTMsR.png)](https://i.stack.imgur.com/BTMsR.png)


I started to do the problem by coordinating H+ with the lone pair of oxygen then after that I can't proceed .please send the solution by show the detailed mechanism.




There are two equally important path for the given reaction: (i) Via protonation of imine $\ce{N}$; and (ii) Via protonation of keto $\ce{O}$.


(i) Protonation of imine $\ce{N}$ would end up with 1,4-addition to give structure (A), which rearranges to structure (B) via keto-enol tautomerism.


(ii) It is also possible that Protonation can be undergone through keto $\ce{O}$, which would end up with 1,4-addition followed by keto-enol tautomerism to give structure (D). See the depicted arrow-pushing mechanism below:


[![possible products](https://i.stack.imgur.com/1Pj5v.jpg)](https://i.stack.imgur.com/1Pj5v.jpg)


To get structure (C), it need to have 1,6-addition, which is impossible. Therefore, the answer is (C).


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