JEE Main Chemistry question

What is the product in the following cross Claisen condensation? C₂H₅COOC₂H₅ + (COOC₂H₅)₂ --C₂H₅ONa, H⁺--> ?

(A)CH₃CH(COOC₂H₅)(COCOOC₂H₅)Correct
(B)CH₃CH(COCOOC₂H₅)₂
(C)CH₃CH(COOCOOC₂H₅)(COOC₂H₅)
(D)CH₃CH(COCOC₂H₅)(COC₂H₅)

Answer: (A)

Solution

Sodium ethoxide deprotonates the α-hydrogen of ethyl propanoate (the only ester here with an enolizable α-CH); this enolate attacks the carbonyl carbon of diethyl oxalate, displacing ethoxide and forming a new C–C bond, giving

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Question ID VK-149492