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Chapter 4: Problem 61

When 3,3-dimethyl-2-butanol is treated with dilute acid, the most stable carbocation formed is (a) 3,3-dimethyl-2-butyl cation (b) 3,3 -dimethyl-1-butyl cation (c) 2,3-dimethyl-2-butyl cation (d) 2-methyl-2-pentyl cation

Short Answer

Expert verified
Answer: The most stable carbocation formed when 3,3-dimethyl-2-butanol is treated with dilute acid is the 3,3-dimethyl-1-butyl cation.

Step by step solution

01

Write the structure of 3,3-dimethyl-2-butanol

First, draw the structure of 3,3-dimethyl-2-butanol. It is an alcohol with the following structure: H3C-C(CH3)2-CH(OH)-CH3
02

Determine the possible carbocations

When 3,3-dimethyl-2-butanol is treated with dilute acid, it forms a carbocation by losing a water molecule. We can eliminate the hydrogen from the alcohol group and draw the possible cations for each option: (a) 3,3-dimethyl-2-butyl cation: H3C-C(CH3)2-CH(+)-CH3 (b) 3,3-dimethyl-1-butyl cation: H3C-C(CH3)2-C(+)-CH2-CH3 (formed through a 1,2-hydride shift) (c) 2,3-dimethyl-2-butyl cation: H3C-CH(C+H2)-C(CH3)2 (d) 2-methyl-2-pentyl cation: H3C-CH(C+H2)-CH2-C(CH3)2
03

Analyze the stability of each carbocation

Evaluate each carbocation based on the number of alkyl groups attached to the positive carbon. The stability order is tert-butyl cation > secondary cation > primary cation because more electron-donating alkyl groups will distribute the positive charge and make the carbocation more stable. (a) 3,3-dimethyl-2-butyl cation: secondary cation, three hyperconjugative structures (b) 3,3 -dimethyl-1-butyl cation: secondary cation, four hyperconjugative structures (c) 2,3-dimethyl-2-butyl cation: primary cation, two hyperconjugative structures (d) 2-methyl-2-pentyl cation: secondary cation, four hyperconjugative structures
04

Choose the most stable carbocation

Based on the number of hyperconjugative structures, the carbocation with the maximum number of hyperconjugative structures will be the most stable. Both options (b) and (d) have four hyperconjugative structures, but option (b) is already formed within the given structure due to the 1,2-hydride shift. Therefore, the most stable carbocation formed when 3,3-dimethyl-2-butanol is treated with dilute acid is: (b) 3,3 -dimethyl-1-butyl cation

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