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Question: When 3, 3-dimethyl-2-butanol is heated with \(H_{2}SO_{4}\) the major product obtained is....

When 3, 3-dimethyl-2-butanol is heated with H2SO4H_{2}SO_{4} the major product obtained is.

A

cis and trans isomers of 2, 3-dimethyl-2-butene

B

3, 3-dimethyl-1-butene

C

2, 3-dimethyl-2-butene

D

2, 3-dimethyl-1-butene

Answer

2, 3-dimethyl-2-butene

Explanation

Solution

CH3−CH−C−CH3∣CH3∣∣OHCH3→H2SO4\underset{OHCH_{3}}{\underset{||}{\overset{CH_{3}}{\overset{|}{CH_{3} - CH - C - CH_{3}}}}}\overset{\quad H_{2}SO_{4}\quad}{\rightarrow}

CH3−C+H−⥂⥂⥂⥂⥂⥂⥂C−CH3+OH−∣⥂⥂⥂CH3∣CH3→Methyl shiftRearrangement2ocarboniumion\underset{2^{o}\text{carboniumion}}{CH_{3} - \overset{+}{C}H - ⥂ ⥂ ⥂ ⥂ ⥂ ⥂ ⥂ \overset{\underset{\overset{CH_{3}}{|}}{\underset{CH_{3}}{| ⥂ ⥂ ⥂}}}{C - CH_{3} + OH^{-}}\underset{\text{Rearrangement}}{\overset{\quad\text{Methyl shift}\quad}{\rightarrow}}}

CH3−CH−∣CH3C−+∣CH3CH33oCarboniumion(Morestable)\underset{3^{o}\text{Carboniumion}\left( \text{Morestable} \right)}{CH_{3} - \overset{\overset{CH_{3}}{|}}{CH -}\overset{\overset{CH_{3}}{|}}{\underset{+}{C -}}CH_{3}}