Chapter 28: Nitration of Methyl Benzoate I. General Information:
- Microscale Nitration of Methyl Benzoate
- May 17, 2008
- Reaction(s), including molar masses and all relevant physical data
- 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.
Materials:
- 6mL of concentrated sulfuric acid
- 30g of methyl benzoate
- Mixture of .2mL of concentrated sulfuric acid and . 2 mL of concentrated nitric acid
- Ice
- 2 mL ice cold methanol
Procedure in
...Brief:
- In a 10 x 100 mm reaction tube add . 30g of methyl benzoate and . 6 mL of concentrated sulfuric acid
- Flick the tube or use magnetic stirring
- Cool the mixture to 0 degrees Celsius
- Add dropwise using a Pasteur pipette a mixture of . 2mL of concentrated sulfuric acid and . 2mL of concentrated nitric acid
- Keep the reaction in ice
- Warm to room temp and pour onto 2. 5g of ice.
- Isolate the solid using suction filtration
- Wash the product with water, followed by . 2ml of ice cold methanol
- Remainder is weighed and recrystallized with an equal weight of methanol
III. Data Collection Weights: Ice:2. 63g Crude Mass:. 33gRefined Mass:.
179g Methanol:0. 2mL 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 degree
Celsius Melting point of refined Methyl 3-nitrobenzoate is 78 degrees
Celsius Our:Crude Mass mp averages to 52. 5 Refined Mass mp averages to 78 Percent Error: Crude: 75-52. 5/75 *100 = 30.0 % error or 70. 0% yield Refined: 78-78/78*100 = 0 % error
This can be a misleading figure, because it assumes that it is correct to average the melting points together to compare their accuracy. . We know that the purified melting point results are a little off because some of the product started melting at 76 degrees, therefore indicating this part of the compound wasn’t completely pure. Yield: Methyl benzoate to Methyl 3-nitrobenzoate is a 1:1 mole ratio
Methyl benzoate:Methyl 3-nitrobenzoate: MW: 136. 6g/mol MW: 181. 15 g/mol Amount Used: . 32g
Determining Theoretical Yield: .32 Theoretical Yield 136.16 = . 0024 moles since 1:1 ratio (181. 15 x . 0024) = 0. 43g Actual Yield = . 33g .33g .43g x 100 = 77% yield or 23 percent error V.
Discussion I believe that we pretty much hit the nail on the head during this lab. III.
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