Chem 243b - Nitration of Methyl Benzoate, A Macroscale Synthesis

Chem 243b - Nitration of Methyl Benzoate, A Macroscale Synthesis

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3B: Nitration of Methyl Benzoate, A Macroscale Synthesis Antonio Alarcon Chem 243B 2/17/08 I. Abstract In this lab an electrophilic aromatic substitution reaction (EAS reaction) was performed on a macroscale. To do so, methyl benzoate was treated with a mixture of nitric acid and sulfuric acid to produce methyl- m -nitrobenzoate. The obtained melting point (MP) proved to be 75 ° C. The obtained IR spectrum positively identified an aromatic group at 3300 cm -1 , a carbonyl group noting the presence of a carboxylic ester at 1200 cm -1 , and a nitro group at 1560 and 1350 cm -1 . The obtained NMR noted one impurity through the existence of a triplet rather than an additional 2*2 split pattern at c .
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II. Introduction Largely due to the unusual stability presented by aromatic compounds, cyclic/conjugated, 150 kJ/mol less negative than expected heat of hydrogenation, and planar 120 ° bond angle length EAS is possible only through the introduction of highly reactive electrophilic reagents. 1 A perfect example of such an EAS reaction lies within the nitration of methyl benzoate to methyl- m -nitrobenzoate as shown below: Throughout the completion of the above listed EAS reaction, one gained significant knowledge pertaining to the normal scale in which reactions are performed.
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This note was uploaded on 04/03/2008 for the course CHEM 243b taught by Professor Padias during the Spring '08 term at University of Arizona- Tucson.

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Chem 243b - Nitration of Methyl Benzoate, A Macroscale Synthesis

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