JEE Main levelSingle correct optionDifficulty 2 of 3o4024
2-Phenylethyl bromide CX6HX5CHX2CHX2Br and its analogue CX6HX5CDX2CHX2Br react with NaOEt in ethanol at the same temperature, and the first reacts about 7 times faster. This result shows that
Athe slow step is ionisation to a primary carbocation
Bthe beta C-H bond is cleaved in the rate-determining step, consistent with E2
Cthe beta C-H bond is not broken in the slow step, so the reaction is E1
Dthe reaction is SN2 at the carbon bearing bromine
Answer: B
A primary isotope effect kH/kD of about 7 is large; it means that the C-H bond to the beta-carbon is being broken in the rate-determining step, as it is in the single-step E2 transition state.