4. (6 points) What is the condensation product if diethyl malonate is used instead of ethyl...
can someone do 1-3? Pechmann Condensation 1. Propose a mechanism for the acid-catalyzed Pechmann condensation of resorcinol and ethyl acetoacetate. Identify the transesterification, electrophilic aromatic substitution and dehydration steps. 2. Would you expect 1,3,5-trihydroxybenzene (phloroglucinol) to react more quickly or more slowly than resorcinol? Why or why not? 3. Consider and discuss the greenness of Pechmann Reaction. 4. Discuss and assign the peaks (chemical shift, splitting pattern, etc) in the 1H NMR and IR spectra of your product INDO,
Malonic ester (diethyl malonate) is treated successively with sodium ethoxide (1 eq.), ethyl bromide, potassium tert-butoxide, isobutyl chloride, hot aqueous NaOH HCI, and heat. What is the final product? 6-Methylheptanoic acid • 2-Ethyl-3-methylpentanoic acid HE Ethylisobutylmalonic acid 4-Ethyl-2-methylpentanoic acid 2 Ethyl-4-methylpentanoic acid
5. (4 points) Aniline and ethyl acetoacetate react under similar conditions as Pechmann condensation. This reaction produces two possible products. Their IR spectra show peaks at 3300 cm1, but no peaks at 1700 cm1 NH2 н* ? ? heat aniline Draw the structures of the two possible products.
Question 4 The base used to deprotonate diethyl malonate is always ethoxide. The base should be the same as the leaving group on the ester. What would happen if hydroxide was used instead? O Nothing, hydroxide is not a strong enough base to deprotonate diethyl malonate O Hydroxide could also act as a nucleophile and do a saponification reaction on the ester O The decarboxylation step would not work with hydroxide Question 5
8. Give a synthesis of the compound shown starting from either diethyl malonate (DEM) or ethyl acetoacetate (EAA) shown in the box below. Give all reagents necessary. State clearly whether your starting compound is DEM or EAA. You do not need to draw the intermediate steps. 17 pts] Eto Et Hoce DEM ΕΑΑ. 9. Draw the uncharged product of this synthetic sequence. [4 pts] 1. KOH OCH 3. NaOH(aq) excess 10. By how much will the mass of this compound...
1. Which of the compounds listed below would produce the following aldol condensation product? 2. Which is not a product of the claisen condensation of ethyl ethanoate and ethyl butanoate? 3. A claisen-schmidt reaction shown below, is an important step in the commercial synthesis of Vitamin A: what type of reaction is the claisen- Schmidt? 4. Which of the following statements is true about the anion formed from the reaction of diethyl malonate with sodium ethoxide? please help A. cycloh...
please answer and explain #9 and #10 e. something else! 9. diethyl malonate + sodium ethoxide / ethanol then PhCH2Br, then dilute acid quench+ heat b. 2-phenylpropanoic acid . 3-phenylpropanoic acid а c. 4-oxo-2-phenylpentanal d. something else! 10. ethyl 2-methylpropanoate + LDA / THF/-78° then CHsI with acetic acid quench Но OEt OEt b. а. d. e. something else! с.
What would happen if you had used a 1:1 mixture of ethyl acetate instead of hexane to elute your column? Would the product (DEET) have come out faster or slower? Would this have improved your separation, or made it worse?
if in project 7.1, 100% ethanol was used as the reaction solvent instead of diethyl ether, what would the product(s) of the reaction be? be sure to explain the formation of your predicted products. 2. If in Project 7.1, 100% ethanol was used as the reaction solvent instead of diethyl ether, what would the product(s) of the reaction be? Be sure to explain the formation of your predicted products. MgBr HOCH CH3
The reaction is the Pechmann reaction of resorcinol and ethyl acetoacetate to form 4-methylumbelliferone: When HCl is added to the product, protonation occurs at the carbonyl oxygen of the ester. Draw the conjugate acid of this reaction and explain why 4-methylumbelliferone is more basic than a typical ester. Note: my professor mentioned something about Lewis acids/bases and mentioned how bases are more electron rich. I would like to explain how the product is more basic than a typical ester using...