Fundamentals of Organic ChemistryChemistryAlcohols Phenols and Ethers
Identify the product [A] among the given options for the following acid-catalyzed rearrangement reaction:
Correct answer
2
Step-by-step solution
The given reaction is an acid-catalyzed rearrangement of a hydroperoxide, known as the Hock rearrangement. First, the hydroperoxide group is protonated by the acid, followed by the loss of a water molecule to create an electron-deficient oxygen atom. An aryl group then migrates from the adjacent carbon atom to the electron-deficient oxygen. The migratory aptitude of aryl groups depends on their ability to stabilize the partial positive charge developed in the transition state. Electron-donating groups increase the