Nitration Of Methyl Benzoate Lab Report
Nitration of Methyl Benzoate
Date of Completion: February 29, 2012 Date Report Submitted: March 14, 2012
Objective of Experiment: The purpose of this experiment is was to synthesize methyl 3-nitro benzoate from methyl benzoate through an electrophilic aromatic substitution reaction.
Chemical Equation:
Materials:
Name of Compound Molecular weight MP/BP Grams Used Moles Used
Methyl benzoate 136.16 g/mol -12.5 OC /199.6 OC 0.28g 2.056*10-3
Sulfuric acid 63.01 g/mol 10 OC /337OC 0.8g 1.2*10-2
Nitric acid 98.08 g/mol -42 OC /83 OC 0.2g 2.039*10-3
Methyl 3-nitro benzoate 181.15 g/mol 78 OC /279 OC 0.107g 5.906*10-4
Procedural Details
To a reaction tube 0.6 mL of concentrated sulfuric acid was added; followed by 0.28g …show more content…
A melting point was preformed with a temperature range of . The final range was , this value was similar to the CRC manual.
Answers to questions assigned
1. Hydrocarbons do not dissolve in concentrated sulfuric acid, but methyl benzoate does. Explain this difference and write an equation showing the ions that are produced.
Hydrocarbons do not dissolve in concentrated sulfuric acid because hydrocarbons are non polar. What causes them to be non polar is that they have an even distribution of electrons between the carbon and hydrogen atoms of 0.3. And as a result this does not result in the formation of an electrophile.
Methylbenzoate, however is polar. Sulfuric acid therefore is able to protonate the methyl benzoate. The sulfuric acid protonates the nitric acid to generate the necessary electrophile. Protonated nitric acid loses water to form a nitronium ion, which is the electrophile required for nitration. Finally, the nitronium ion is reacted with the protanated intermediate at the meta position.
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2. What would you expect the structure of the dinitro ester to be? Consider the directing effects of the ester and the first nitro group upon the addition of the second nitro
Date of Completion: February 29, 2012 Date Report Submitted: March 14, 2012
Objective of Experiment: The purpose of this experiment is was to synthesize methyl 3-nitro benzoate from methyl benzoate through an electrophilic aromatic substitution reaction.
Chemical Equation:
Materials:
Name of Compound Molecular weight MP/BP Grams Used Moles Used
Methyl benzoate 136.16 g/mol -12.5 OC /199.6 OC 0.28g 2.056*10-3
Sulfuric acid 63.01 g/mol 10 OC /337OC 0.8g 1.2*10-2
Nitric acid 98.08 g/mol -42 OC /83 OC 0.2g 2.039*10-3
Methyl 3-nitro benzoate 181.15 g/mol 78 OC /279 OC 0.107g 5.906*10-4
Procedural Details
To a reaction tube 0.6 mL of concentrated sulfuric acid was added; followed by 0.28g …show more content…
A melting point was preformed with a temperature range of . The final range was , this value was similar to the CRC manual.
Answers to questions assigned
1. Hydrocarbons do not dissolve in concentrated sulfuric acid, but methyl benzoate does. Explain this difference and write an equation showing the ions that are produced.
Hydrocarbons do not dissolve in concentrated sulfuric acid because hydrocarbons are non polar. What causes them to be non polar is that they have an even distribution of electrons between the carbon and hydrogen atoms of 0.3. And as a result this does not result in the formation of an electrophile.
Methylbenzoate, however is polar. Sulfuric acid therefore is able to protonate the methyl benzoate. The sulfuric acid protonates the nitric acid to generate the necessary electrophile. Protonated nitric acid loses water to form a nitronium ion, which is the electrophile required for nitration. Finally, the nitronium ion is reacted with the protanated intermediate at the meta position.
F
2. What would you expect the structure of the dinitro ester to be? Consider the directing effects of the ester and the first nitro group upon the addition of the second nitro