Chapter 28: Nitration of Methyl Benzoate

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Chapter 28: Nitration of Methyl Benzoate

I.General Information:
A.)Microscale Nitration of Methyl Benzoate
C.)May 17, 2008
D.)Reaction(s), including molar masses and all relevant physical data E.)Mechanism for the nitration of chlorobenzene:

II.Purpose: In this experiment we are to take a cold solution of an aromatic ester that is first dissolved in sulfuric acid and is then reacted with nitric acid. This is a highly exothermic reaction and is kept under control by means of cooling; after which the mixture is poured onto ice. The solid product will then be isolated by filtration and recrystallized from methanol, in which it is very soluable.

1).6mL of concentrated sulfuric acid
2).30g of methyl benzoate
3)Mixture of .2mL of concentrated sulfuric acid and .2 mL of concentrated nitric acid 4)Ice
5).2 mL ice cold methanol

B.)Procedure in Brief:
1)In a 10 x 100 mm reaction tube add .30g of methyl benzoate and .6 mL of concentrated sulfuric acid 2)Flick the tube or use magnetic stirring
3)Cool the mixture to 0 degrees Celsius
4)Add dropwise using a Pasteur pipette a mixture of .2mL of concentrated sulfuric acid and .2mL of concentrated nitric acid 5)Keep the reaction in ice
6)Warm to room temp and pour onto 2.5g of ice.
7)Isolate the solid using suction filtration
8)Wash the product with water, followed by .2ml of ice cold methanol 9)Remainder is weighed and recrystallized with an equal weight of methanol

III.Data Collection

Crude Mass:.33g
Refined Mass:.179g
Methyl Benzoate: .32g
Melting Ranges:

Crude Mass:45-62 Celsius
Refined Mass:76-80 Celsius

IV.Sample Calculations

Ideal:Melting point of crude Methyl 3-nitrobenzoate of 74 – 76 degrees Celsius Melting point of refined Methyl 3-nitrobenzoate is 78 degrees Celsius

Our:Crude Mass mp averages to 52.5
Refined Mass mp...
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