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t-butyl chloride to t-butanol mechanism

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t-butyl chloride (Compound A) generates either tert-butanol (Compound B) or 2-methyl-1-propene (Compound C) in the presence of water as shown below:

Please see attachment for diagram.

(a) Product B is the result of what type of reaction? Circle one.

Sn1 Sn2 E1 E2

(b) Product C is the result of what type of reaction? Circle one.

Sn1 Sn2 E1 E2

(c) Which would be the expected major product of this reaction? Circle one.

Product B Product C

(d) Provide a good arrow-pushing mechanism for the formation of product B in this reaction, showing all intermediates clearly.

(e) Would the rate of the reaction increase by adding additional water? Explain why or why not in one brief sentence.

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a. Substitution, tertiary alkyl ...

Solution Summary

The mechanism of the conversion of t-butyl chloride to t-butyl alcohol is shown. Effect of water on the rate of the reaction is explained.