Problems and exercisesAcylation reactions: Claisen, Dieckmann and others
Exercise 1
Ethyl 2-methylpropanoate does not undergo the Claisen condensation with sodium ethoxide in ethanol, but it does with triphenylmethylsodium. Explain.
Exercise 2
Which product does diethyl pimelate (diethyl heptanedioate) give in the Dieckmann condensation? And diethyl 3-methyladipate? Explain the regioselectivity of the second.
Exercise 3
Propose a synthesis of 1-phenylbutane-1,3-dione (benzoylacetone) by a crossed Claisen condensation.