Reaction of 2 -methylpropene with CH3 OH in the presence of H2 SO4 catalyst yields methyl tert-b

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Reaction of 2 -methylpropene with CH3 OH in the presence of...

Reaction of 2 -methylpropene with $\mathrm{CH}_{3} \mathrm{OH}$ in the presence of $\mathrm{H}_{2} \mathrm{SO}_{4}$ catalyst yields methyl tert-butyl ether, $\mathrm{CH}_{3} \mathrm{OC}\left(\mathrm{CH}_{3}\right)_{3},$ by a mechanism analogous to that of acid-catalyzed alkene hydration. Write the mechanism, using curved arrows for each step.

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Key Concepts

Acid-Catalyzed Electrophilic Addition

This concept involves the initial protonation of an alkene by a strong acid, which converts an electron-rich double bond into a more electrophilic species. The process is fundamental to many reactions, such as hydration and ether synthesis, as it prepares the substrate for subsequent nucleophilic attack by generating a reactive intermediate.

Carbocation Intermediate Stability

A key aspect of these reactions is the formation of carbocation intermediates. The stability of these intermediates, often enhanced by hyperconjugation and inductive effects, dictates the reaction pathway and product distribution. In acid-catalyzed processes, more substituted carbocations (such as tertiary carbocations) are typically favored due to their greater stability.

Nucleophilic Attack and Deprotonation

Once a stable carbocation intermediate is formed, it becomes susceptible to attack by nucleophiles like alcohols. The nucleophilic attack leads to the formation of an oxonium ion, which subsequently loses a proton to yield a neutral product. This sequence of steps—nucleophilic addition followed by deprotonation—is central to the formation of ethers in acid-catalyzed conditions.

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