Igama Emmanuel
Dec 11, 2023
Reaction of 2-methylpeopene with CH3OH in the presence of H2SO4 catalyst yields methyl tert-butyl ether, CH3OC(CH3)3, by a mechanism analogous tothat of acid catalysed alkane hydration.Write the mech?
Organic chemistry
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Dec 11, 2023
The reaction of 2-methylpropene with CH3OH in the presence of H2SO4 catalyst proceeds through an acid-catalyzed addition-elimination mechanism. Here is the step-by-step mechanism:
Step 1: Protonation of 2-methylpropene
H2SO4 acts as a strong acid and donates a proton to the double bond of 2-methylpropene, resulting in the formation of a carbocation intermediate.
CH3CH=C(CH3)2 + H2SO4 → CH3CH+(CH3)2 + HSO4-
Step 2: Nucleophilic attack by CH3OH
The nucleophilic oxygen of CH3OH attacks the positively charged carbon of the carbocation intermediate, forming a new bond.
CH3CH+(CH3)2 + CH3OH → CH3CH(OCH3)(CH3)2
Step 3: Proton transfer
In this step, a proton is transferred from the oxygen of CH3OH to the sulfate ion (HSO4-) to regenerate the H2SO4 catalyst.
CH3CH(OCH3)(CH3)2 + HSO4- → CH3CH(OCH3)(CH3)2 + H2O
Overall reaction:
CH3CH=C(CH3)2 + CH3OH → CH3CH(OCH3)(CH3)2
The final product is methyl tert-butyl ether (MTBE), CH3OC(CH3)3.
Step 1: Protonation of 2-methylpropene
H2SO4 acts as a strong acid and donates a proton to the double bond of 2-methylpropene, resulting in the formation of a carbocation intermediate.
CH3CH=C(CH3)2 + H2SO4 → CH3CH+(CH3)2 + HSO4-
Step 2: Nucleophilic attack by CH3OH
The nucleophilic oxygen of CH3OH attacks the positively charged carbon of the carbocation intermediate, forming a new bond.
CH3CH+(CH3)2 + CH3OH → CH3CH(OCH3)(CH3)2
Step 3: Proton transfer
In this step, a proton is transferred from the oxygen of CH3OH to the sulfate ion (HSO4-) to regenerate the H2SO4 catalyst.
CH3CH(OCH3)(CH3)2 + HSO4- → CH3CH(OCH3)(CH3)2 + H2O
Overall reaction:
CH3CH=C(CH3)2 + CH3OH → CH3CH(OCH3)(CH3)2
The final product is methyl tert-butyl ether (MTBE), CH3OC(CH3)3.
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