Ch_322a_6.012

Ch_322a_6.012 - A Mechanism for the SN1 Reaction of t-Butyl...

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A Mechanism for the S N 1 Reaction of t-Butyl Chloride in Water The overall stoichiometry of this reaction is: CH 3 -C-Cl CH 3 CH 3 + 2H 2 O CH 3 -C-OH CH 3 CH 3 H 3 O + + + Cl - Rate = k [t-butyl chloride] The reaction of tert-butyl chloride with water to produce tert-butyl alcohol shows first-order kinetics : This S N 1 reaction proceeds by a multi-step mechanism of the Case A type described above with a slow (rate-determining) first step .
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A Proposed Mechanism with a Carbocation Intermediate (1) CH 3 -C-Cl CH 3 CH 3 slow step CH 3 -C CH 3 CH 3 + + Cl - t-butyl carbocation a high energy intermediate RDS (2) CH 3 -C CH 3 CH 3 + + O-H H : : nucleophile fast CH 3 -C CH 3 CH 3 + O-H H t-butyloxonium ion (3) CH 3 -C CH 3 CH 3 + O-H H + O-H H : base fast CH 3 -C CH 3 CH 3 O-H + H 3 O + acid bond heterolysis nucleophilic addition proton exchange
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Free Energy Progress of Reaction (CH 3 ) 3 C-Cl + 2H 2 O CH 3 -C CH 3 CH 3 + + 2H 2 O + Cl - key intermediate (CH 3 ) 3 COH 2 + + H
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Ch_322a_6.012 - A Mechanism for the SN1 Reaction of t-Butyl...

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