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PRACTICE PROBLEM
1-Chloro-3-methyl-2-butene undergoes hydrolysis in a mixture of water and dioxane at a rate that is more than a thousand times that of 1-chloro-2-butene.
(a) What factor accounts for the difference in reactivity?
(b) What products would you expect to obtain? [Dioxane is a cyclic ether (below) that is miscible with water in all proportions and is a useful cosolvent for conducting reactions like these. Dioxane is carcinogenic (i.e., cancer causing), however, and like most ethers, it tends to form peroxides.]
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Chapter 15 Solutions
Organic Chemistry
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