Question

please don't use any abbreviations! like I don't know how to draw anything like oet or an R group like please just draw out the whole thing!

CH3 CO2Et Hagemann's ester The compound known as Hagemann's ester is prepared by treatment of a mixture of formaldehyde and ethyl acetoacetate with base, followed by acid-catalyzed decarboxylation. The reaction involves the following steps: 1. Deprotonation of ethyl acetoacetate to form enolate ion 1; 2. Reaction of the enolate ion with formaldehyde to form tetrahedral intermediate 2; 3. Protonation and dehydration to form unsaturated intermediate 3; 4. Michael reaction between a second ethyl acetoacetate enolate and the unsaturated intermediate to form enolate ion 4; 5. Proton transfer to form enolate ion 5; 6. Internal aldol cyclization to form cyclohexenone 6; 7. Acid-catalyzed ester hydrolysis to form carboxylic acid 7; 8. Decarboxylation to form the final product. Write out the mechanism on a sheet of paper and then draw the structure of cyclohexenone 6. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • Do not include lone pairs in your answer. They will not be considered in the grading. IC- OOO OF Down

Answer 1

Solverion prepration of Hagemann's Ester Base 1. Hc-H сна formaldehyde Ethyl acetoacetate (male) (2 male ) Mechanism Depostanation -of Ethyl acetoacetate to. form enolare.ion Oet - He EE erolate on A Reachon * Reaction of Enolate ion with intermediare; formaldehyde to foom terreinedral o Er dehy.doarim oli portonation de Z OEK Tuh .Unsaturated intermediate michail reathon between a seconol, ethyl acetoacetate enoleté and unsaturated intermediobe to form erolare ion 11 Der oft michael reachion?

) profon townsfer to form emolare ion proron traiga . Enotate in ritermal Aldol condensation ER #lololi eyalization to form cyclonere none ( sing Acid-catalyzed ester hydrolysis to form carboxylic Quiole Base

Carboxylic acid e Decarboxy cation to from the final product Hagemann's, ester Cethyl-2-methyl-4-020 -2.cyl&ohexenelasboylu). Cyclonerenone

Above step by step mechanism to synthesise Hagemann's Ester by knovengel method of prepration.

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