Nitration of Methyl Benzoate Data and Mechanisms PDF

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Nitration of Methyl Benzoate Data and Mechanisms...

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Figure 1: Figure 1 shows the mechanism for the formation of the nitronium ion from the reagents nitric acid and sulfuric acid.

! Figure 2: Figure 2 shows the mechanism for the formation of methyl m-nitrobenzoate from the reactants methyl benzoate and nitronium ion.

Figure 3: Figure 3 shows the mechanism for the formation of methyl o-nitrobenzoate from the reactants methyl benzoate and nitronium ion.

Figure 4: Figure 4 shows the mechanism for the formation of methyl p-nitrobenzoate from the reactants methyl benzoate and nitronium ion.

Table 1: Table of Reagents Compound

Molecular Weight (g/mol)

Boiling Point (°C)

Melting Point (°C)

Density (g/ cm3)

32.04

64.7

-97.8

0.79

methyl benzoate

136.15

199.0

-12.4

1.09

methyl m-nitrobenzoate

181.15

—

78.0-80.0

—

methyl o-nitrobenzoate

181.15

—

-13.0

—

methyl p-nitrobenzoate

181.15

—

94.0-96.0

—

nitric acid

63.01

83.0

-41.6

1.51

nitronium ion

46.01

—

-9.3

—

sulfuric acid

98.07

337.0

10.3

1.83

water

18.02

100.0

0.0

1.00

methanol

Equation 1: Equation 1 shows the two calculations to determine the limiting reagent. Methyl benzoate is the limiting reagent, and 2.20x10-3 mol is the theoretical yield.

Equation 2: Equation 2 shows the calculation for the actual yield, which is 4.03x10-4.

Equation 3: Equation 3 shows the formula and calculation for percent yield which is 18.32%.

Table 3: Proton NMR Analysis for m-Nitrobenzoate Label

Multiplicity

Integration

Shift (ppm)

A

1

3

3.9

B

3

1

7.7

C

2

2

8.5

D

1

1

8.9...