JEE Advanced levelSingle correct optionDifficulty 3 of 3ap179
Propene is treated with HBr in the presence of peroxide to give X. X is converted to its Grignard reagent with Mg in dry ether, which is treated with ethanal and then HX3OX+. The final alcohol is
Apentan-2-ol
Bpentan-3-ol
Cbutan-2-ol
D2-methylpentan-2-ol
Answer: A
Peroxide effect gives the anti-Markovnikov bromide, CHX3CHX2CHX2Br. Its Grignard reagent CHX3CHX2CHX2MgBr adds to ethanal (CHX3CHO) to give a secondary alkoxide. Hydrolysis gives CHX3CH(OH)CHX2CHX2CHX3, pentan-2-ol.