Question

What product(s) are formed when the shown ether is heated with hydrogen iodide?

(a) (C6H5)CH2I and (C6H5)OH

(b) (C6H5)CH2OH and (C6H5)I

(c) (C6H5)CH2OH and (C6H5)CH2I

(d) (C6H5)OH and (C6H5)I

The question was posed to me in a job interview.

I'm obligated to ask this question of Ethers topic in division Alcohols, Phenols and Ethers of Chemistry – Class 12

Answer 1

The correct choice is (a) (C6H5)CH2I and (C6H5)OH

Explanation: The C-O bond of the phenol group is stronger than the C-O bond of the ether and alkyl aryl group. This is due to the partial double bond character because of sp^2 hybridised C-O cond. Therefore, the weaker C-O bond is broken and two major products, viz., phenol and iodomethyl benzene, are formed.