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After the mass of the crude product was measured, the recrystallization was done for more purification; the solution looked clear prior to it’s cooling to room temperature. After the solution cooled to the room temperature and vacuum filtration was done again on recrystallization product, the solution was a white shiny with crystalline solid appearance. The melting point of the Meta-Methyl nitrobenzoate product formed was at 76.2 ‐ 78°C. The appearances of the TLC for the crude product, starting material and recrystallized appear to the similar; they all looked dark brown under the UV light. Also, their Rf values indicate that the recrystallized solute moved less distance compare to the crude product and started material. This suggests that the product made was Meta-Methyl nitrobenzoate even if it has little different melting point from the literature melting point which is 7880°C. Conclusion/Discussion: During the electrophilic aromatic substitution reaction between methyl benzoate and a nitrating solution of sulfuric and nitric acids, the Meta-Methyl nitrobenzoate product was obtained based on the product melting point range. Percent yield of the crude 56.42% and the percent yield of the recrystallized product was 52.59%. This would indicate that during the recrystallization there was a reduction in the percentage yield of the production. The obtained final product melting point rang was 76.2-780C. This would show that the experimental melting point was very close to the literature value of 78 -
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The one located at 1730.1 cm was the result of a carbonyl group and
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the peak at 1617.7 cm-1 specified the existence of a benzene ring. Another peak at 1151.5 cm-1 indicates a C—O bond, which is presented in methyl m-nitrobenzoate. The peak at 739.9 cm indicated that the product was meta-substituted benzene. All of the shown
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peaks supported that the product was methyl m-nitrobenzoate. Using 1H NMR the meta-substituted product can identity and differentiated from para- and ortho- substitution. For example, the chemical shifting at 3.99ppm showed the methyl group of the methyl benzoate. Using the coupling constant would also explain that there is an existence of methyl m-nitrobenzoate between 7.2 and 8.9ppm. As shown in the table result, the coupling constant of the pare appear to be smaller, for example, it is about 72 Hz. Meta is has the next lowest value which is about 103Hz and finally ortho appear to be at about 652 Hz. Therefore, the substitution of ortho or para, appear be
substituted at a less favorable position compare to the meta
The one located at 1730.1 cm was the result of a carbonyl group and
-1
the peak at 1617.7 cm-1 specified the existence of a benzene ring. Another peak at 1151.5 cm-1 indicates a C—O bond, which is presented in methyl m-nitrobenzoate. The peak at 739.9 cm indicated that the product was meta-substituted benzene. All of the shown
-1
peaks supported that the product was methyl m-nitrobenzoate. Using 1H NMR the meta-substituted product can identity and differentiated from para- and ortho- substitution. For example, the chemical shifting at 3.99ppm showed the methyl group of the methyl benzoate. Using the coupling constant would also explain that there is an existence of methyl m-nitrobenzoate between 7.2 and 8.9ppm. As shown in the table result, the coupling constant of the pare appear to be smaller, for example, it is about 72 Hz. Meta is has the next lowest value which is about 103Hz and finally ortho appear to be at about 652 Hz. Therefore, the substitution of ortho or para, appear be
substituted at a less favorable position compare to the meta