Ch_322a_6.025

Ch_322a_6.025 - The E1 Reaction The reaction of tert-butyl...

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The E1 Reaction The reaction of tert-butyl chloride in the mixed solvent of 80% ethanol-20% water at 25 o C yields a product mixture from two competing reaction paths: substitution and elimination . CH 3 CCl CH 3 CH 3 83% CH 3 C-OR CH 3 CH 3 R = H, CH 3 CH 2 - 17% CH 2 =C CH 3 CH 3 substitution elimination The rate of formation of isobutene is given by: Rate = k e [tert-butyl chloride] first-order kinetics The notation for this reaction that shows first order kinetics is E1 . Note that the rate expression for the E1 reaction has the same kinetic form as the S N 1 reaction: Rate = k s [tert-butyl chloride] first-order kinetics k e /k s = 17/83, the ratio of the two products.
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A Mechanism for the Competing E1/S N 1 Reactions These two competing reactions have the same rate-determining step : bond heterolysis to produce the tert-butyl carbocation: CH 3 CCl CH 3 CH 3 RDS slow step CH 3 C CH 3 CH 3 + + Cl - tert-butyl carbocation bond heterolysis After the rate-determining step, two competing modes of reaction
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Ch_322a_6.025 - The E1 Reaction The reaction of tert-butyl...

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