Tert-butyl alcohol reacts with aqueous hydrochloric acid to give tert-butyl chloride. (CH3)3COH(aq) — Kinetics Chemistry Question
Question
Tert-butyl alcohol reacts with aqueous hydrochloric acid to give tert-butyl chloride.
(CH3)3COH(aq) + H+(aq) + Cl–(aq) → (CH3)3CCl(aq) + H2O(l)
For this reaction, Rate = k[(CH3)3COH][H+]. With which mechanism is this rate law consistent?
(CH3)3COH(aq) + H+(aq) ⇌ (CH3)3C(OH2)+(aq) fast
(CH3)3C(OH2)+(aq) + Cl–(aq) → (CH3)3CCl(aq) + H2O(l) slow
(CH3)3COH(aq) + H+(aq) ⇌ (CH3)3C(OH2)+(aq) fast
(CH3)3C(OH2)+(aq) → (CH3)3C+(aq) + H2O(l) slow
(CH3)3C+(aq) + Cl–(aq) → (CH3)3CCl(aq) fast
(CH3)3COH(aq) + Cl–(aq) → (CH3)3CCl(aq) + OH–(aq) slow
OH–(aq) + H+(aq) → H2O(l) fast
(CH3)3COH(aq) → (CH3)3C+(aq) + OH–(aq) slow
(CH3)3C+(aq) + Cl–(aq) → (CH3)3CCl(aq) fast
OH–(aq) + H+(aq) → H2O(l) fast