An Experiment to Predict the Effect of Electrophilic Aromatic Substitution on Substituent Orientation and Determine the Product's Identity

Pages: 4 (723 words) Published: February 25, 2014

Objective: To perform an electrophilic aromatic substitution reaction, predict the effect on substituent orientation, and determine the identity of the product and mechanism for product.

Procedure:
Schoffstall, A.M., Faddis, B.A., and Durelinger, M.L. Microscale and Miniscale Organic Chemistry Laboratory Experiments, 2nd Ed., McGraw-Hill, 2004, pages 215-218.

Experiment 12.2 A
Changes: Part A- No methanol recrystallization.

Results and Observations
* all literature values were obtained at www.sigmaaldrich.com Chemical
Volume (mL)
Mass (g)
Density (g/mL)
Molecular Weight (g/mol)
Methyl-3-nitrobenzoate
-
0.1178
-
181.15
Methyl benzoate
2.00
-
1.088
136.00
Sulfuric Acid
0.60
-
1.840
98.08
Nitric Acid
0.15
-
1.510
63.01

Chemical
MP Exp. (°C)
MP lit (°C)
Methyl-3-nitrobenzoate
72.6-75.7
78.0-80.0

Mmole Calculations:
HNO3 (16M)- 0.15 mL* (0.016 mole/mL) = 0.0024 mole* (1000 mmol/mole) = 2.4 mmoles H2SO4 (18M)- 0.60 mL* (0.018 mole/mL) = 0.0108 mole*(1000 mmol/mole) = 10.8 mmoles Limiting Reagent Calculation:
methylbenzoate - 2.0 mL*(1.088g/mL)/( 136.00g/mol)= 0.016 mol Methylbenzoate is limiting reagent because it was starting material used in electrophilic aromatic substitution reaction. Percent Yield:

Theoretica yield- 2.176g/(136.0g/mol)*(181.15 methyl-3-nitrobenzoate g/mol) = 2.8984g Mass product/theoretical yield =0.1178g/2.8984g= 4.1% Yield

Methylbenzoate, sulfuric acid, nitric acid clear colorless liquids. Methanol clear colorless liquid. After addition of acids to methylbenzoate, turned yellowish red. Red coloration likely from azo dye contamination. Disscussion:

The objective of this experiment was to perform an electrophilic aromatic substitution reaction, predict the effect on substituent orientation, and determine the identity of the product and mechanism for product. The limiting reagent in this reaction was methylbenzoate because it...
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