JEE Main levelSingle correct optionDifficulty 2 of 3ap005
(CHX3)X3C−CH=CHX2 (3,3-dimethylbut-1-ene) is heated with dilute aqueous HX2SOX4. The major alcohol formed is
A3,3-dimethylbutan-2-ol
B3,3-dimethylbutan-1-ol
C2,3-dimethylbutan-2-ol
D2,3-dimethylbutan-1-ol
Answer: C
Protonation gives the secondary cation (CHX3)X3C−CH(+)−CHX3, which rearranges by a methyl shift to the more stable tertiary cation (CHX3)X2C(+)−CH(CHX3)X2. Water attacks this cation, giving 2,3-dimethylbutan-2-ol.