320 Part Three Properties and Reactions of Organic Compounds groups, respectivel

Question

320 Part Three Properties and Reactions of Organic Compounds groups, respectively. Compare your spectrum to thet shown in Figure 1. Your instructor may also want you to determine the 'H and C spectra. The spectra may be run in CDCly or DMSO-d The 'H spectrum 1500 MHz CDCly is shown in Figure 2. Assignments have been made on the spectrum using data from a paper by Delaude, Grandjean, and Noels (see refer ences below.) No attiempt has been made to analyze the phenyl resonances, other than to show the integral value (10 H) for the two monosubstituted benzene rings. For reference, the SC spectrum (75 MHz, CDClJ shows 17 peaks: 14.1, 363, 44.3, 59.8,61.1, 124.3, 126.4, 1275, 1272 129.0, 129.1, 130.7 1379, 141.2, 158.8, 169.5, and 194.3 REFERENCES García-Raso, A.; García-Raso, J: Campaner, B; Mestres, R; Sinisterra, J. V. An Improved Procedure for the Michael Reaction of Chalcones. Synthesis 1982, 9, 1037 García-R Raso, A; Garcia-Raso, J: Sinisterra. J. V; Mestres, R. Michael Addition and Aldol Condensations A Simple Teaching Model for Organic Laboratory: J. Chem. Educ. 1986 63, 443. Delaude, L: Grandjean, Ji Noels,A. F. The Step-by-Step Robinson Annulation of Chalcone and Ethyl Acetoacetate. J.Chem.Educ. 2006, 83, 1225-1228 and supplementary materi- als submitted with this article. QUESTIONS 1. Why was it possible to separate the product from sodium hydroxide using acetone? 2. The white solid that remains in the centrifuge tube after acetone extraction fizzes when hydrochloric acid is added, suggesting that sodium carbonate is present. How did this substance form? Give a balanced equation for its formation. Also give an equation for the reaction of sodium carbonate with hydrochloric acid. 3. Draw a mechanism for each of the three steps in the preparation of the 6-ethoxy- carbonyl-35-diphenyl- tions as a base and ethanol serves as a proton source. You may assume that sodium hydroxide func- . Indicate how you could synthesis trans-chalcone.(Hint: sce Experiment 37) 60 50 30 4000 3500 3000 2500 2000 1500 1000 500 KBr.

Explanation / Answer

1. If the product has solubility in acetone then it is possible to separate out the product from NaOH using acetone because in that case the product will dissolve in acetone but NaOH will not get dissolve in acetone, so we can easily separate out acetone from NaOH and then acetone can be easily evaporated to obtain the product.

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