Name: 111 points Show all calculations. Answer alone is not acceptable. No reaction is an acceptable answer. Densities in g/ml Ether (diethylether) MW 74 g. d=0.7 g/ml ethyl cyclohexanecarboxylated= 0.95 g/ml Ethanol (Ethyl alcohol) d=0.8 g/ml Methylene chloride (dichloromethane, DCM) d-1.33 g/ml Methanol (methyl alcohol) d=0.8 g/ml Isoproanol (2-propanol) d=0.8 g/ml Benzene d-0.874 Sulfuric acid d-1.84 g/ml Acetic acid (glacial), d-1.05 g/ml, Molecular weight 60.0 MW Benzene 78.11 Phosphorous 30.97 Chlorine 35.5 Nitrogen 14.00 Oxygen 16.00 Carbon 12.00 Hydrogen 1.00 Bromine 80.00 Magnesium 24.30 Potassium 39.1 "Novel carboxamide derivatives as HIV inhibitors and their preparation and use in the treatment of viral mediated diseases." Reddy, Bandi Parthasaradhi; Krishna, Bandi Vamsi; Sharma, Vedula Manohar; Reddy, Kura Rathnakar, Reddy, Musku Madhanmohan; Subrahmanyam, Lanka V. L.; Kumar, Mamnoor Prem. (Hetero Research Foundation, India). WO 2011061590 (US designated) Filed November 10, 2010 and Published May 26, 2011 The synthesis of ethyl cyclohexanecarboxylate was published in the world application above. CH,CH₂OH . ethanol . H₂O cyclohexanecarboxylic acid (ethyl alcohol) ethyl cyclohexanecarboxylate To cyclohexanecarboxylic acid (10 grams) in ethanol (150 ml), sulfuric acid (8.64 ml) was added and the reaction refluxed for 6 hours at about 80° C. Upon completion of the reaction (monitored by TLC), ethanol was evaporated under reduced pressure. The residue was washed with water, and then neutralized with saturated sodium bicarbonate. The organic residue was extracted with dichloromethane (DCM) and dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography using 5% ethyl acetate in hexane as the eluent to furnish the title compound (12 g) as a light yellow liquid. The proton NMR and mass spec are consistent for the product. 1. What is the molecular formulae & molecular weight of cyclohexane carboxylic acid? How many moles of cyclohexane carboxylic acid were used? 2. What is the molecular formulae & molecular weight of ethanol? How many moles & grams of ethanol were used during this reaction? 3. After the removal of ethanol under reduced pressure, the residue was washed with water. Why was that done? 4. After the water wash, the residue was neutralized with sodium bicarbonate. What was being neutralized? Be specific. 5. What is the formula for sodium bicarbonate? After the neutralization with sodium bicarbonate, the organic residue was extracted with dichloromethane (DCM). In which layer is the product? Top or Bottom? Explain your reasoning. 6. Why was the organic layer dried over sodium sulfate used? Did a chemical reaction occur? If so, draw the chemical reaction. Be specific. 7. If sodium sulfate were not available, would magnesium sulfate be an acceptable substitute? Why or why not? What is the molecular formula for sodium sulfate? 8. What is the molecular weight of the product ethyl cyclohexanecarboxylate? What is the theoretical yield of ethyl cyclohexanecarboxylate? What is the theoretical yield in moles for ethyl cyclohexanecarboxylate? What is the theoretical yield in grams for ethyl cyclohexanecarboxylate? 9. The reported yield for this reaction is 12 grams. Find its actual yield in moles. Find the actual percent yield. Give the name of the type of reaction this is.