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What is the mechanism and intermediates involved in the reaction of tert-butyl alcohol and hydrochloric acid to produce tert-butyl chloride?

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The reaction of tert-butyl alcohol  t-BuOH  with hydrochloric acid  HCl  to produce tert-butyl chloride  t-BuCl  is an example of an acid-catalyzed substitution reaction, specifically a nucleophilic substitution at a tertiary carbon  SN1 mechanism .Here is the step-by-step mechanism and intermediates involved in this reaction:1. Protonation of tert-butyl alcohol: The oxygen atom of the tert-butyl alcohol molecule acts as a nucleophile and attacks the hydrogen atom of the hydrochloric acid molecule. This results in the formation of a protonated tert-butyl alcohol  t-BuOH2+  and a chloride ion  Cl- .Intermediate: Protonated tert-butyl alcohol  t-BuOH2+ 2. Formation of carbocation: The protonated tert-butyl alcohol molecule undergoes heterolysis, where the bond between the oxygen and the tertiary carbon breaks. The oxygen atom takes both electrons from the bond, leaving a positively charged tert-butyl carbocation  t-Bu+  and a water molecule  H2O .Intermediate: Tert-butyl carbocation  t-Bu+ 3. Nucleophilic attack: The chloride ion  Cl-  acts as a nucleophile and attacks the positively charged tert-butyl carbocation  t-Bu+ , forming a new bond between the chloride ion and the tertiary carbon. This results in the formation of the tert-butyl chloride  t-BuCl  product.Product: Tert-butyl chloride  t-BuCl Overall, the reaction proceeds through two intermediates: protonated tert-butyl alcohol  t-BuOH2+  and tert-butyl carbocation  t-Bu+ . The mechanism involves an acid-catalyzed nucleophilic substitution at a tertiary carbon  SN1 mechanism .
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