Methyl benzoate by fischer esterification

I) Pre-lab section: 1) Fill in the blanks (A-F) for the following calculation table (12 pts): Name Molecular Weight Amount mol or mmol Equivalents Density Benzoic Acid 122.12 3.5g A 1.0 - Methanol 32.04 B 310 mmol - 0.791 g/mL Sulfuric Acid 98.08 1.5mL 0.0275 mol - C Methyl Benzoate 136.15 D E F - A: B: C: D: E: F: 2) What is your limiting reagent in this experiment and why? You can show calculations/explain your choice. (3 pts) 3) What would the theoretical yield of this reaction be? Please show your calculations for this part clearly. (3 pts) 4) Complete the chemical reaction and show the reaction mechanism below (5 pts): II) During Lab Section: 1) You have chloroform and water in the separatory funnel. (3 pts) 2) 3) a. Which layer (top, bottom) will be organic and aqueous? b. Why do you think so? c. How will you check if your assumption is right? Name a drying agent (3 pts): a. Why do we use a drying agent in this experiment? b. How much of the drying agent should be used? List two things that the wash with 0.6 M NaHCO3 does in this experiment (3 pts): a. What gas is liberated at this time? 4) Let’s say you were using your phone during lab, and you were distracted. While performing the last step in your work-up (adding brine or saturated sodium chloride) in your separatory funnel, you accidentally drained a good amount of your aqueous layer into your organic layer How would you remedy this problem? (3 pts) 5) How did we separate the chloroform from the methyl benzoate in this lab? Why did simple distillation work for this purification? (3 pts) III) Post-lab Section: 1) Match the following spectra with their corresponding chemical structures AND explain your decision in 2-3 sentences for each one. Just to clarify, each NMR spectra corresponds to a different chemical structure (12 pts). 1) 2) 3) 1H NMR Spectra 3H 1H 4H total (7-7.5ppm) IR Spectra Mass Spectra M+ Peak: 136 ...
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