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SN1 substitution and E1 elimination frequently compete in the same reaction. (a) Propose

Chapter 7, Problem PROBLEM 7-17

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QUESTION:

SN1 substitution and E1 elimination frequently compete in the same reaction. (a) Propose a mechanism and predict the products for the solvolysis of 2-bromo-2,3,3-trimethylbutane in methanol. (b) Compare the function of the solvent (methanol) in the E1 and SN1 reactions.

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QUESTION:

SN1 substitution and E1 elimination frequently compete in the same reaction. (a) Propose a mechanism and predict the products for the solvolysis of 2-bromo-2,3,3-trimethylbutane in methanol. (b) Compare the function of the solvent (methanol) in the E1 and SN1 reactions.

ANSWER:

Step 1 of 3

SN1is the type of substitution where the substrate affects the rate of the reaction. E1 elimination reaction is a type of unimolecular elimination reaction, which is similar to the mechanism of SN1 since both are unimolecular, and the reaction mechanism of both proceeds via carbocation formation.

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