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Identify the intermediates and the mechanism involved in the reaction of tert-butyl alcohol with hydrochloric acid to form tert-butyl chloride.

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ago by (139k points)
The reaction of tert-butyl alcohol  t-BuOH  with hydrochloric acid  HCl  to form tert-butyl chloride  t-BuCl  is an example of an acid-catalyzed substitution reaction  specifically, an SN1 reaction .The mechanism involves the following steps:1. Protonation of the alcohol: The oxygen atom in the tert-butyl alcohol molecule is protonated by the hydrochloric acid, forming a protonated tert-butyl alcohol intermediate  t-BuOH2+ . This step is reversible.t-BuOH + HCl  t-BuOH2+ + Cl-2. Formation of the carbocation: The protonated tert-butyl alcohol intermediate undergoes heterolysis, breaking the O-H bond and releasing a water molecule. This results in the formation of a tert-butyl carbocation intermediate  t-Bu+ , which is a highly reactive species.t-BuOH2+  t-Bu+ + H2O3. Nucleophilic attack: The chloride ion  Cl-  acts as a nucleophile and attacks the carbocation, forming the tert-butyl chloride product.t-Bu+ + Cl-  t-BuClIn summary, the intermediates involved in this reaction are the protonated tert-butyl alcohol  t-BuOH2+  and the tert-butyl carbocation  t-Bu+ . The mechanism is an SN1 reaction, which involves the formation of a carbocation intermediate and a nucleophilic attack by the chloride ion.
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