Synthesis (Predict the Reagents Needed) Question

[PoochGroup]

Hey guys,

 

I am going through practice exams I have found online to prepare for the MCAT. I was wondering if I am on the right track with these synthesis questions. For the second last one, my best assumption was an alkyl shift having to have occurred because the position of the functional group changed and even though alkyl shifts typically occur at third degree carbon centres, I thought that the aromatic phenol could stabilize the secondary carbon through hyperconjugation.

 

Thanks.

 

[hypervalent_iodine]

Your carbocation rearrangement appears to be halfway there. If you used HCl as your source of H+, you'd end up with a Cl in the benzylic position. I can think of one fairly straight forward way to get from there to your product.

[PoochGroup]

HCl, followed by NaOH, right? But the mechanism can only involve one step in this case. What would be another way to do this in one step? Thanks.