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Two substitution products result from the reaction of

Chapter 9, Problem 22P

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QUESTION:

Problem 22P

Two substitution products result from the reaction of 3-chloro-3-methyl-1-butene with sodium acetate (CH3COO-Na+) in acetic acid under conditions that favor an SN1 reaction. Identify the products.

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QUESTION:

Problem 22P

Two substitution products result from the reaction of 3-chloro-3-methyl-1-butene with sodium acetate (CH3COO-Na+) in acetic acid under conditions that favor an SN1 reaction. Identify the products.

ANSWER:

Solution 22P

Step 1 of 3

3-Chloro-3-methyl-1-butene undergoes  reaction to form more stable allylic carbocation. The formed allylic carbocation can be stabilized by its resonance. Its resonance contributors are as shown below:

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