Abstract: The nitration processes of methyl benzoate and recrystallization of crude product Methyl-3-nitrobenzoate were successful with the confirmation of the product’s Infrared spectrum analysis and MelTemp observation. An amount 6.566g Methyl-3-nitrobenzoate was recovered with 75.7% yield comparing to 8.66g of theoretical yield.

Statement and purpose
The purpose of this experiment was to nitrate methyl benzoate to generate Meta substituted Methyl-3-nitrobenzoate (C8H7NO4)
Introduction
Nitration of 6ml of methyl benzoate by nitronium ions which are supplied by the mixture of HNO3 and H2SO4 are typical electrophilic aromatic substitution reaction. The ester group of methyl benzoate is electron withdrawing group will deactivate the aromatic …show more content…
Next, the crude product was recrystallized by using ethanol and yielded 6.566g of pure product. According to the reaction equation, Methyl-3-nitrobenzoate was expected to be the pure product. Therefore, the melting point of the pure product was taken. At the first trial, the power of MelTemp was set at level 4, and the melting range was observed to be 60oC – 65oC; however, it wasn’t the same as true melting range of Methyl-3-nitrobenzoate which has the melting range of 76oC – 80oC (Ref 5). The second trial was performed. This time, the level of the MelTemp was set at level 3, and the melting range was observed to be 75oC – 76oC. This melting range was really close to the true melting range of Methyl-3-nitrobenzoate. The reason why second trial was performed, because during the first trial, the setting of the power level of the MelTemp was high; therefore, the temp probe failed to measure the melting point properly. During the second trial, the power level was set at a lower level; hence the measuring of the temp probe was more precise. Even though the melting point of the expected Methyl-3-nitrobenzoate product was performed, it was still not enough to confirm that the product was actual Methyl-3-nitrobenzoate. An Infrared Spectrum (IR spectrum) of the pure product was run (see attached page). The analysis of the IR spectrum is explained …show more content…
Additionally, the IR spectrum of Methyl-3-nitrobenzoate was also performed and the analysis of the IR was matched corresponding to the structure of Methyl-3-nitrobenzoate. The experimental amount of product was lowered than the expected amount which was 8.66g due to the unavoidable error during the experiment. Finally the % yield of the reaction was 75.8%
Post lab Question
1. By using 6.00 ml of methyl benzoate and the density of methyl benzoate, the mol of methyl benzoate we are supposed to used is calculated below:
(6.00 ml C8H8O2 × 1.0837 g/ml C8H8O2) / 63.0119g C8H8O2 = 0.0478 mol C8H8O2
2. We only get mono-substituted aromatic ring because of the deactivating, electron withdrawing group, ester, of methyl benzoate. It slows down and prevents di- and tri-nitration.
3. Since ethers functional group of anisole is a activating group, so the nitronium ion will attacks on either para- or ortho- position of aromatic ring. The structures are presented as