Exams › JEE Advanced › Chemistry
Which of the following statements about nucleophilic substitution reactions are correct?
- The rate of hydrolysis of tert-butyl bromide increases when Ag2O is added to the reaction mixture
- Aqueous Ag2O generates nucleophilic OH⁻ ions in solution
- CH3CH2Cl reacts more slowly than PhCH2Cl in bimolecular nucleophilic substitution (SN2)
- The order of SN2 reactivity is: CH3Cl < CH3CH2Cl < CH3CH(Cl)CH3
Correct answer: CH3CH2Cl reacts more slowly than PhCH2Cl in bimolecular nucleophilic substitution (SN2)
Solution
Ag2O in water generates Ag⁺ which removes the leaving group (Br⁻) as AgBr, promoting SN1 ionization — it acts as a Lewis acid, not by producing nucleophilic OH⁻. PhCH2Cl (benzyl chloride) has enhanced SN2 reactivity relative to ethyl chloride due to partial carbocation stabilization and empty d-like orbital overlap in the transition state. The SN2 order is CH3Cl > CH3CH2Cl > secondary > tertiary, so option D is wrong. Options A and C are correct.
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