Lab Report #12 - Google Docs

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The City College of New York, CUNY *

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Chemistry

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Jan 9, 2024

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pdf

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Habiba Elaaidy 12/5/2022 Nitration of Methyl Benzoate Aim The purpose of this experiment is to synthesize methyl nitrobenzoate from methyl benzoate; Using Nitric acid and Sulfuric acid through electrophilic aromatic substitution reaction. Introduction Aromatic situation reactions are a type of organic reaction where an atom that is attached to the aromatic system is replaced by an electrophile. These reactions tend to be electrophilic due to a high electron density within the ring of benzene. An electrophile is positive ion that is trying to bond with another inorder to get more electrons, these positively charged ions want to react with the aromatic ring. The most common mechanism for electrophilic aromatic substitution is the arenium ion mechanism. The arenium ion mechanism refers to carbocation that is attached to the benzene ring.
Table of Physical Properties and Hazards Compound Name Molecular Structure Molecular Formula Molecular Weight g/mol Boiling Point (°C) Melting Point (°C) Hazard and Toxicity Methyl benzoate C 8 H 8 O 2 136.15 199°C -15°C Harmful if swallowed Nitric acid HNO₃ 63.01 83°C -42°C May intensify fire; oxidizer Causes severe skin burns and eye damage Fatal if inhaled Sulfuric acid H₂SO₄ 98.079 337°C 10°C Causes severe skin burns and eye damage Ethanol C₂H₆O 46.07 78.37°C -114.1°C Highly Flammable liquid and vapor Methyl 3-nitrobenzoate C8H7NO4 181.04 279 °C 80 °C May cause eye irritation. May cause skin irritation. May be harmful if absorbed through the skin. May cause irritation of the digestive tract.
Procedure To complete this experiment, first, prepare an ice bath, and then in two small test tubes, place 0.5 mL of Nitric acid in one and 0.6 mL of sulfuric acid in the other. Allow the test-tubes to sit on ice for 10 minutes, then using a glass pipet, transfer the nitric acid dropwise into the tube of the sulfuric acid. In Erlenmeyer flask, place o.5 mL of Methyl benzoate and 1.o mL of sulfuric acid, and place the mixture on ice the nitrating solution was then placed dropwise into the Erlenmeyer flask allow the flask to sit in the ice bath for 30 mins mixing every 5 minutes. Place 1o mL of chilled water into a clean beaker and slowly mix in the solution into the beaker. Allow it to sit for 5 minutes. And set up a vacuum filtration system then filter out the crystals. Results Mass of Final Product = 0.515 g Theortical Yeild Mass of methyl benzoate= 0.54 g (0.5 mL) Mass of nitric acid= 0.71g (0.5 mL) Mass of sulfuric acid= 2.94g (1.6 mL) Moles of methyl benzoate= 0.54 g/136.1487 g/mol= 0.00397 mol (limiting reagent) Moles of nitric acid= 0.71 g/63.01284 g/mol= 0.01128mol Moles of sulfuric acid= 2.94 g/98.07848 g/mol= 0.02997 mol (0.00397 mol)( 181.1463 g/mol)= 0.71915 g
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Percent Yeild (0.515 g/0.71915 g) x 100 = 71.61% We where able to successfully achieve a 71.61% yield from this experiment. Refrences PubChem. (n.d.-a). Ethanol . PubChem. Retrieved December 11, 2022, from https://pubchem.ncbi.nlm.nih.gov/compound/Ethanol#datasheet=LCSS PubChem. (n.d.-b). Methyl 3-nitrobenzoate . PubChem. Retrieved December 11, 2022, from https://pubchem.ncbi.nlm.nih.gov/compound/Methyl-3-nitrobenzoate PubChem. (n.d.-d). Methyl benzoate . PubChem. Retrieved December 11, 2022, from https://pubchem.ncbi.nlm.nih.gov/compound/Methyl-benzoate#datasheet=LCS S§ion=GHS-Classification PubChem. (n.d.-e). Nitric acid . PubChem. Retrieved December 11, 2022, from https://pubchem.ncbi.nlm.nih.gov/compound/nitric_acid PubChem. (n.d.-f). Sulfuric acid . PubChem. Retrieved December 11, 2022, from https://pubchem.ncbi.nlm.nih.gov/compound/Sulfuric-Acid#datasheet=LCSS&s ection=GHS-Classification