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Multiple Choice
Predict the structures of organopalladium compound A and coupling product B in the following reaction sequence.
A
B
C
D
Verified step by step guidance
1
Identify the starting material: The compound is a cycloalkene with an acetate leaving group. The acetate group is positioned on a carbon adjacent to the double bond.
Understand the role of Pd(PPh3)4: This is a palladium catalyst used in cross-coupling reactions. It will facilitate the formation of an organopalladium intermediate by oxidative addition.
Predict the structure of compound A: The acetate group will leave, and the palladium catalyst will form a bond with the carbon that was attached to the acetate, creating an organopalladium species.
Consider the reaction with the diester: The organopalladium compound A will undergo a nucleophilic attack on the diester, facilitated by the base NaOEt, leading to the formation of a new carbon-carbon bond.
Predict the structure of compound B: The final product will be a cycloalkene with the diester moiety attached at the position where the palladium was initially bonded, completing the coupling reaction.