When *o*-bromotoluene is forcefully reacted directly with highly concentrated aqueous at extremely h — Haloalkanes and Haloarenes Chemistry Question
Question
When *o*-bromotoluene is forcefully reacted directly with highly concentrated aqueous $NaOH$ at extremely high temperatures ($340^\circ C$) and immense pressure, a distinct mixture of two specific isomeric products is cleanly isolated. What are these two products?
💡 Solution & Explanation
The reaction of this unactivated aryl halide securely requires extreme conditions and specifically proceeds smoothly via the benzyne mechanism. The forced elimination of $HBr$ generates a highly reactive triple bond safely between the $1$ and $2$ carbons. The hydroxide nucleophile subsequently attacks either side of this symmetrical benzyne bond, cleanly yielding a mixture of *o*-cresol and *m*-cresol.