Need help to calculate the number of moles and the mass of sulfuric acid 36EXPERIMENT 2: NITRATION OF METHYL BENZOATE TYL BENZOATEWash the product once with 10 mL of cold water and then with two 10-mL portions of ice-coldmethanol.4. Weigh the crude product and then recrystallize the solid from an equal mass of methanol heated tonear boiling. Addition of water is not necessary for this recrystallization. If you use a minimumamount of hot methanol to dissolve the crude product, the pure substance will crystallize out nicelywhen cooled to room temperature. As usual, cool the mixture further in an ice bath for about 5 to10 minutes.5. Collect the product, dry it in air, weigh it, take the MP, and the IR spectrum (using the Buck IRspectrometer). Interpret the IR spectrum and be sure to point out the absorptions which identify thecarbonyl peak, the aromatic and the aliphatic hydrogens, the nitro group and meta substitution. SeeAppendix 4 for IR out-of-plane C-H bending vibrations to distinguish between ortho, meta andpara disubstitution. Compare your IR spectrum and MP to what is reported in the literature or theInternet. Determine the % yield. Hand in your product in a labeled polyethylene bag.Post-Lab Questions:1. How many moles of methyl benzoate were you supposed to use? Show your calculations.2. Why do we get only mono-substitution even though we use a slight excess of nitratingagent?3. What would the structure of the product be if anisole (methoxybenzene) were nitratedinstead of methyl benzoate?4. Why is the temperature of the nitration kept under 15 °C?entrated sulfuric acid and5. When methyl benzoate dissolves in sulfuric acid a chemical reaction occurs. How does thestructure of the methyl benzoate change when it is dissolved in sulfuric acid? Give themechanism with the use of curved arrows to show the change taking place.6. Draw all of the resonance structures of the intermediate involved when methyl benzoate isnitrated in this experiment. Experiment 2: NITRATION OF METHYL BENZOATEPurpose: Methyl benzoate is to be nitrated with nitronium ion that is generated in situ.Theory: The nitration of methyl benzoate is a typical electrophilic aromatic substitution reaction,with the ester group being an electron withdrawing substituent and a deactivator. This slows downand prevents di- and tri-nitration, which would yield high energy and potentially explosiveproducts. Nitric acid, in the presence of sulfuric acid, forms the reactive electrophile, nitroniumion (NO₂), according to the reaction shown below:5. Col the product,HNO3 + 2 H₂SO4The nitronium ion then attacks the protonated methyl benzoate at the meta position, which releasesa proton from the ring. When the solution is neutralized, the methyl 3-nitrobenzoate crystallizesout of the solution and can be purified by recrystallization from methanol.OCH3OCH3LOCH 3Post-Lab Questions:NO₂+ +How maagent?HHmethyl benzoate→ NO₂ + 2 HSO4 + H3O+Sure+H-HNO₂+HH+NO₂methyl 3-nitrobenzoateProcedure: (As usual, prepare a Table of Reagents & Expected Products in your notebook beforeyou arrive at the lab.)CAUTION! Concentrated sulfuric acid and nitric acid are corrosive. The liquid andmist cause severe burns to all body tissue. Inhalation may cause lung and tooth damage.Avoid skin contact or inhalation of fumes. Reaction of these acids with water is highlyexothermic and can cause the water to boil and "spit." Be careful not to splatter anywater into the concentrated acid! WORK INSIDE A HOOD!1. In a hood, place 12 mL of concentrated sulfuric acid (equivalent to how many moles?) into a 250-mL Erlenmeyer flask and cool it to 0 °C with an ice bath. Then add 6.0 mL of methyl benzoate.Cool the mixture to 0-10 °C.2. Prepare a nitration mixture by adding an ice-cold solution of 4.0 mL of concentrated nitric acid(equivalent to how many moles?) to 4.0 mL of cold concentrated sulfuric acid. This solution isslowly added to the methyl benzoate-sulfuric acid solution, dropwise with the aid of a Pasteurpipette. During the addition be sure to swirl the flask carefully and keep the pot temperaturebetween 5 and 15 °C.3. When all of the nitric acid mixture has been added, allow the mixture to warm up to roomtemperature, and then after about 15 minutes, pour the entire mixture onto 50 g of cracked ice in a250-mL beaker. After all of the ice has melted, isolate the solid product via suction filtration.35

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10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...