Fundamentals of Organic ChemistryChemistryAlcohols Phenols and Ethers
2-Methylpropan-2-ol can be obtained by the acid-catalyzed hydration of which of the following alkenes?
Options
- ACH ₃ CH ₂ CH = CH ₂
- BAny of the above
- CCH ₃ CH = CHCH ₃
Correct answer
C. CH ₃ CH = CHCH ₃
Step-by-step solution
Target molecule: 2-methylpropan-2-ol, which has the structure (CH₃)₃C-OH . Acid-catalyzed hydration of alkenes proceeds via the formation of a carbocation intermediate, following Markovnikov's rule. - Hydration of 1-butene ( CH ₃ CH ₂ CH = CH ₂ ) forms a secondary carbocation, yielding 2-butanol. - Hydration of 2-butene ( CH ₃ CH = CHCH ₃ ) also forms a secondary carbocation, yielding 2-butanol. - The structure in option (C) is 2-methylpropene ( (CH₃)₂C=CH₂ ). Protonation of the double bond yields a highly stable t