Fundamentals of Organic ChemistryChemistryAlcohols Phenols and Ethers
Identify the product(s) formed in the following reaction:
Options
- ABoth A and B
Correct answer
A. Both A and B
Step-by-step solution
The given reactant is 2-phenylethyl tosylate with an isotopic label ( ¹⁴C ) at the -carbon: Ph-CH₂-¹⁴CH₂-OTs . The reagent is sodium methoxide ( CH₃ONa ) in methanol ( CH₃OH ), which provides the strong nucleophile CH₃O^- . For a primary substrate reacting with a strong nucleophile, the bimolecular nucleophilic substitution ( S_N2 ) mechanism is highly favored over neighboring group participation (NGP) by the phenyl group. In the S_N2 mechanism, the methoxide ion directly attacks the -carbon, displacing the tosylat