Tasked to make 3-chloro-2,2-dimethylbutane from 3,3-dimethylbutan-2-ol. When 2-chloro-2,3-dimethylbutane is obtained as the major product, while 3-chloro-2,2-dimethylbutane is formed as the minor product. 3,3-dimethylbutan-2-ol + HCl ----> 3-chloro-2,2-dimethylbutane + 2-chloro-2,3-dimethylbutane a) Draw the overall reaction showing the starting material, reaction conditions and both the major and minor products (indicate which product is major/minor). b) Draw a comparative energy diagram showing the formation of both major and minor product from the starting materials to explain how the energy differences lead to these experimental results. c) How would you modify the reaction conditions to make 3-chloro-2,2-dimethylbutane the major product. Would changing the mechanism help?
Tasked to make 3-chloro-2,2-dimethylbutane from 3,3-dimethylbutan-2-ol. When 2-chloro-2,3-dimethylbutane is obtained as the major product, while 3-chloro-2,2-dimethylbutane is formed as the minor product.
3,3-dimethylbutan-2-ol + HCl ----> 3-chloro-2,2-dimethylbutane + 2-chloro-2,3-dimethylbutane
a) Draw the overall reaction showing the starting material, reaction conditions and both the major and minor products (indicate which product is major/minor).
b) Draw a comparative energy diagram showing the formation of both major and minor product from the starting materials to explain how the energy differences lead to these experimental results.
c) How would you modify the reaction conditions to make 3-chloro-2,2-dimethylbutane the major product. Would changing the mechanism help?
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