Question ochem

[OSUkid]

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Someone explain I'm thinking the tertiary OH gets H. Leaves generating carbocation. Primary OH loses H from HSO4- since its a base so O- attacks carbonation. Can someone explain thanks

 

[OSUkid]

Wait nevermind, the H2SO4 only represents acidic conditions for primary alcohol to ethers. So H30 will donate H to primary OH, it leaves, then the tertiary OH attacks positive carbon, creating a cycloskeleton, then a workup step right?

 

[Dwight Beet Farm]

Tertiary OH gets protonated by the acid. The primary OH will attack the positively charged electrophilic H2O on the tertiary carbon. After it displaces it as H2O, HSO4 can now take its proton back from the OH!

 

[DrNutmeg]

The tertiary OH is protonated because when H2O leaves, the tertiary carbocation is more stable than the primary carbocation.