Consider the following reaction and identify the product (P). [figure] 3-Methylbutan-2-ol
- CH3CH=CH-CH3
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Answer
(4) [figure]
Solution
The reaction follows the SN1 path. Protonation and loss of water give a 2° carbocation:
(CH3)2CH-CH(OH)-CH3 H+, -H2O (CH3)2CH- CH-CH3
A 1,2-hydride shift gives the more stable 3° carbocation:
(CH3)2CH- CH-CH3 (CH3)2 C-CH2-CH3
Br- attacks the 3° carbocation, giving 2-bromo-2-methylbutane:
(CH3)2 C-CH2-CH3 + Br- (CH3)2CBr-CH2-CH3
Answer: (4)