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2-methylpropene to tert-butyl alcohol Reaction Mechanism
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Natasha Goldman
2-methylpropene to tert-butyl alcohol Reaction Mechanism
It is an acid-catalyzed hydration of the double bond. First, the double bond is protonated to yield the tert-butyl cation which is most stabilized by hyperconjugation (protonation at C2 would form a less stable primary cation). The cation is captured by nucleophilic attack of water, which after deprotonation yields tert-butanol and the regenerated proton.
It is an acid-catalyzed hydration of the double bond. First, the double bond is protonated to yield the tert-butyl cation which is most stabilized by hyperconjugation (protonation at C2 would form a less stable primary cation). The cation is captured by nucleophilic attack of water, which after deprotonation yields tert-butanol and the regenerated proton.
It is an acid-catalyzed hydration of the double bond. First, the double bond is protonated to yield the tert-butyl cation which is most stabilized by hyperconjugation (protonation at C2 would form a less stable primary cation). The cation is captured by nucleophilic attack of water, which after deprotonation yields tert-butanol and the regenerated proton.
$$\ce{(H3C)2C=CH2 + H3O+ <=> (H3C)3C+ + H2O} \tag 1$$
$$\ce{(H3C)3C+ + H2O <=> (H3C)3C-OH2^{+}} \tag 2$$
$$\ce{(H3C)3C-OH2^{+} + H2O ->~ (H3C)3C-OH + H3O+} \tag 3$$
It is an acid-catalyzed hydration of the double bond. First, the double bond is protonated to yield the tert-butyl cation which is most stabilized by hyperconjugation (protonation at C2 would form a less stable primary cation). The cation is captured by nucleophilic attack of water, which after deprotonation yields tert-butanol and the regenerated proton.
$$\ce{(H3C)2C=CH2 + H3O+ <=> (H3C)3C+ + H2O} \tag 1$$
$$\ce{(H3C)3C+ + H2O <=> (H3C)3C-OH2^{+}} \tag 2$$
$$\ce{(H3C)3C-OH2^{+} + H2O ->~ (H3C)3C-OH + H3O+} \tag 3$$
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