Ethyl 3-oxobutanoate is treated successively with (i) NaOEt, then CH3CH2Br; (ii) NaOEt, then CH3I; (iii) hot aqueous NaOH, then dilute acid and warming. The final product is

JEE Advanced levelSingle correct optionDifficulty 3 of 3g3075

Ethyl 3-oxobutanoate is treated successively with (i) $NaOEt$ , then $CH X_{3} CH X_{2} Br$ ; (ii) $NaOEt$ , then $CH X_{3} I$ ; (iii) hot aqueous $NaOH$ , then dilute acid and warming. The final product is

The

CH X_{2}

between the two carbonyls is deprotonated and alkylated twice, giving

CH X_{3} CO - C (CH X_{3}) (C X_{2} H X_{5}) - COOEt

. Hydrolysis and acidification give the beta-keto acid, which loses

CO X_{2}

on warming. The remaining

CH X_{3} CO - CH (CH X_{3}) (C X_{2} H X_{5})

is 3-methylpentan-2-one.