Electrophilic Aromatic Substitution Reaction Lab

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
The limiting reagent in this reaction was methylbenzoate because it was starting material used in electrophilic aromatic substitution reaction (0.016 moles). There were 10.8 mmoles of H2SO4 and 2.4 mmoles HNO3 used in this experiment. The mass of the product obtained from this experiment was 0.1178g. Experimental melting point of the product was 72.6-75.7°C. A percent yield of 4.1% was obtained for this experiment. The major product obtained from this experiment was methyl-3-nitrobenzoate. The structure of the compound is shown