(Solved): synthesis of dimedone from diethyl malonate and mesityl oxide \( \Longrightarrow \) \( \mathrm{C}_ ...

synthesis of dimedone from diethyl malonate and mesityl oxide \( \Longrightarrow \) \( \mathrm{C}_{2} \mathrm{H}_{5} \mathrm{O}_{2} \mathrm{CCH}_{2} \mathrm{CO}_{2} \mathrm{C}_{2} \mathrm{H}_{5} \) \( \left(\mathrm{CH}_{3}\right)_{2} \mathrm{C}=\mathrm{CHCOCH}_{3} \) Diethyl Malonate Mesityl Oxide A) Write a mechanism for the addition of diethyl malonate to mesityl oxide in the presence of sodium ethoxide/ethanol b) Write a mechanism for the cyclisation step of the synthesis. c) Write a mechanism for the hydrolysis of the ester. d) Write a mechanism for the decarboxylation step of the synthesis, illustrating the activated complex involved. - Give a brief discussion of keto-enol tautomerism and list some reasons why one form predominates over another. Compare/contrast the factors that contribute to the high enol contents found in dimedone and 2,4-pentadione (acetylacetone). - Give the IUPAC names for dimedone and its enol tautomer. - Suggest a synthesis of mesityl oxide from starting materials of three carbons or less.