You are a manager for a company, Weighty Matters, that specializes in the manufacture of organic compounds

Question:

You are a manager for a company, Weighty Matters, that specializes in the manufacture of organic compounds containing ¹⁸O, a heavy isotope of oxygen. You have assigned the task of preparing ether B to a team of two staff experts, and you have stipulated that alcohol A must be used as a starting material (*O = ¹⁸O): A CH3 OH B CH3 -CH3

A member of your staff, Homer Flaskclamper, has proposed the following two possible syntheses and has come to you for advice. (1) (2) CH3 OH CH3 * OH HSO4 (trace) CH3OH NaH CHzl CH3 CH3 CH3 * CH3