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I've been given the following exercise in organic chemistry, and I'm at a complete loss. The text book doesn't cover the subject at all. I have some knowledge of melonic ester synthesis. As an undergraduate student in biology, I have a really hard time grasping the concepts, so an in-depth explanation would be much appreciated.

The acetoacetic ester synthesis is closely related to the melonic ester synthesis, but involves alkylation with the anion of ethyl acetoacetate rather than diethyl malonate. Treatment of the ethyl acetoacetate anion with an alkyl halide, followed by decarboxylation, yields a ketone product: Treatment of the ethyl acetoacetate anion with an alkyl halide, followed by decarboxylation, yields a ketone product How would you prepare the following compound using an acetoatic ester synthesis? enter image description here

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  • $\begingroup$ Can you identify what R would give you this structure? X is normally a halogen (Cl, Br, I) $\endgroup$ – Waylander Dec 4 '19 at 14:48
  • $\begingroup$ Could R be the aromatic ring with bromide attached? $\endgroup$ – Kristian Jensen Dec 4 '19 at 15:21
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    $\begingroup$ better if it is the aromatic ring with CH2Br attached $\endgroup$ – Waylander Dec 4 '19 at 15:37
  • $\begingroup$ Thank you. Would it possible to do the exercise without being given the contens of the first picture. And if so, how would one do it? $\endgroup$ – Kristian Jensen Dec 4 '19 at 15:48
  • $\begingroup$ Diethyl malonate + sodium ethoxide in ethanol, add benzyl bromide. When that reaction is complete add 5N HCl to pH1. Heat to reflux until reaction complete. Concentrate, partition the residue between water and Ethyl Acetate. Product is in the ethyl acetate phase. $\endgroup$ – Waylander Dec 4 '19 at 16:21

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