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When Ethyl Acetoacetate Is Treated with One Equivalent of Ethoxide δ\delta

Question 189

Essay

When ethyl acetoacetate is treated with one equivalent of ethoxide ion followed by one equivalent of 1,2-dibromoethane compound,X is produced.Treatment of X with a second equivalent of ethoxide,produces Y.Further treatment of this product to conditions of saponification,acidification and heating produced a product,Z,that gives the following spectral data:
1H NMR: 0.88 δ\delta multiplet 13C NMR: Broad Band Decoupled: 10.40,21.17,29.84,
208.30 δ\delta
1.00 δ\delta multiplet DEPT 90: 21.17 δ\delta
1.96 δ\delta multiplet DEPT 135: positive signals at 21.17,29.84 δ\delta
2.24 δ\delta singlet negative signals at 10.40 δ\delta
What is a reasonable structure for Z?

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