Write the structure(s) of the major product(s) obtained when 2-chloro-2,3-dimethylbutane

Chapter 7, Problem 1

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Write the structure(s) of the major product(s) obtained when 2-chloro-2,3-dimethylbutane (either enantiomer) reacts with (a) sodium ethoxide (EtONa) in ethanol (EtOH) at 80 8C or (in a separate reaction) with (b) potassium tert-butoxide (t-BuOK) in tert-butyl alcohol (t-BuOH) at 80 8C. If more than one product is formed, indicate which one would be expected to be the major product. (c) Provide a detailed mechanism for formation of the major product from each reaction, including a drawing of the transition state structures.

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