New answers tagged

2

Here is a mechanism for the cleavage. After proton transfer, the carbocation has a resonance contributor. Nucleophilic attack can occur on the ethyl group because there is a good leaving group. The electrophilic addition can happen, with iodide attacking the carbocation. However, it is reversible. Iodide is a good leaving group, and the carbocation is ...


2

I have used the image you used $2nd$, see carefully the markings. The $C-O$ bond with benzene ring is stronger than the $C-O$ bond of ethyl, as there is resonance with benzene making it partially a double bond. So, that $C-O$ is difficult to break compared to the $C-O$ bond in ethyl branch.


Top 50 recent answers are included