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Phenol reacts with excess ethyl iodide (C2H5I) in the presence of sodium ethoxide (C2H5ONa) in anhydrous ethanol. What is the major product?
- C6H5OC2H5
- C6H5I
- C6H5OC6H5
- C2H5OC2H5
Correct answer: C6H5OC2H5
Solution
Under the Williamson ether synthesis conditions, phenol is deprotonated by sodium ethoxide to form sodium phenoxide (C6H5O-Na+). The phenoxide ion acts as a nucleophile and displaces iodide from ethyl iodide via SN2 to give phenyl ethyl ether (C6H5OC2H5, phenetole). The excess ethoxide and ethyl iodide simply form diethyl ether as a byproduct but the main product from phenol is C6H5OC2H5.
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