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Which of the following statements about nucleophilic substitution reactions is/are correct? (i) The rate of hydrolysis of tert-butyl bromide increases upon addition of Ag2O. (ii) Aqueous Ag2O acts as a source of nucleophilic OH- ions. (iii) CH3CH2Cl is less reactive than PhCH2Cl in a bimolecular nucleophilic substitution (SN2) reaction. (iv) The order of SN2 reactivity is: CH3Cl < CH3CH2Cl < CH3CH(Cl)CH3.

1. Only (i) and (ii) are correct
2. Only (ii) and (iii) are correct
3. Only (i), (ii) and (iii) are correct
4. Only (iii) and (iv) are correct

Correct answer: Only (i) and (ii) are correct

Solution

tert-Butyl bromide undergoes SN1; Ag+ removes Br- and aqueous Ag2O provides nucleophilic OH-, so both (i) and (ii) are correct. PhCH2Cl is actually more reactive than CH3CH2Cl in SN2 (benzylic activation), so (iii) is wrong. SN2 rate order is CH3Cl > CH3CH2Cl > CH3CH(Cl)CH3 (steric hindrance increases), so (iv) is also wrong.

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