7. Substitution Reactions
Substitution Comparison
7:20 minutes
Problem 6.56
Textbook Question
Textbook QuestionThe following reaction takes place under second-order conditions (strong nucleophile), yet the structure of the product shows rearrangement.
Also, the rate of this reaction is several thousand times faster than the rate of substitution of hydroxide ion on 2-chlorobutane under similar conditions.
Propose a mechanism to explain the enhanced rate and rearrangement observed in this unusual reaction. (“Et” is the abbreviation for ethyl.)
<IMAGE> -OH—> <IMAGE> + Cl-
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