Ethyl benzoate is treated with (i) excess C2H5MgBr, dry ether; (ii) H3O+. The product is

1-phenylpropan-1-one (propiophenone)

JEE Advanced levelSingle correct optionDifficulty 3 of 3o1090

Ethyl benzoate is treated with (i) excess $C X_{2} H X_{5} MgBr$ , dry ether; (ii) $H X_{3} O X^{+}$ . The product is

The first equivalent adds and expels ethoxide, giving propiophenone. The ketone is more reactive than the ester and adds a second

C X_{2} H X_{5} X^{-}

to give

C X_{6} H X_{5} - C (OMgBr) (C X_{2} H X_{5}) X_{2}

. Hydrolysis gives

C X_{6} H X_{5} - C (OH) (C X_{2} H X_{5}) X_{2}

, 3-phenylpentan-3-ol.