COMEDK202510 May 2025Evening ShiftChemistryAlcohols Phenols and EthersActual
Which one of the following is the major product formed when the given reaction occurs?
Correct answer
2
Step-by-step solution
The reaction involves the cleavage of an ether and the hydrohalogenation of an alkene with excess concentrated HI. First, the ether linkage Ar-O-CH₂CH₃ is cleaved by HI. The oxygen atom is protonated, and the iodide ion attacks the less sterically hindered alkyl group ( CH₂CH₃ ) via an S_N2 mechanism, resulting in the formation of a phenol ( Ar-OH ) and ethyl iodide ( CH₃CH₂I ). Second, the alkene group -CH=CH₂ attached to the benzene ring undergoes electrophilic addition with HI. According to Markovnikov's rule, t