I found an organic chemistry question which asked the major product of the following reaction -
The mechanism for the same in the answer was -
My questions regarding this are as follows -
The molecule has two oxygen atoms, one as an epoxide and the other as ketone. How do we decide which oxygen atom accepts the proton? Seeing the mechanism provided in the answer, I reasoned that the epoxide oxygen is sp3 hybridized, hence less electronegative than the ketone oxygen, which is sp2 hybridized. Hence as the less electronegative atom it donates its lone pair to the proton. Am I correct? If not, what is the real reason?
Acid-catalyzed opening of epoxide follows SN1 mechanism, which implies more stable carbocation must be formed. In the given mechanism, however, the carbocation is formed on the right side, where the carbonyl group exerts -I effect and destabilizes the carbocation. I could not make sense of this.
Are there any specific rules as to which site is attacked by the proton if multiple nucleophilic sites are present in the molecule? Also, is my reasoning in (2) correct?
I am also open to the fact that the given mechanism in the image may be wrong, in which case, I would also like to know the correct mechanism and product.