Mechanism of preparation of m nitrobenzoic acid from methyl benzoate

Chem-Org-Lab

Lab Report: Multi-Step Synthesis Part I and Part II: Electrophilic aromatic substitution of benzoic acid to produce m-nitrobenzoic acid; Fisher Esterification of m-nitrobenzoic acid to produce methyl m-nitrobenzoate

Reading Assignment:

Handout: Pedersen, S.; Myers, A.; Gilbert, J.C.; Martin, S.F.; Williamson, K.L.; Masters, K.M.; Hill, N.; Esselman, B.; Organic Chemistry lab I/ II; (Chem lab 336/337); Custom Edition For Cleveland State University; Cengage Learning; 2015; ISBN:1-305-76438-2

For Reflux: Lab book; Chapter 7, page 87-88

For Filtration: lab book, Chapter 9, page 132-141

For Recrystallization: lab book, Chapter 15 page 221-235

**When writing on your lab report, be aware that your work will be checked against all the students of all the course sections, including past sections. You can have your friends to help you brain storm the assignment, but plagiarized work and identical/partially identical work will be easily identified by your TAs and instructor. No credit will be given to plagiarized work, besides to be considered an academic misconduct, to be punished in accord with the academic code of conduct.**

Part I report ___/30

Part II report ___/30

Total ___/30

Lab Report Part I:

Multi-step synthesis part I: electrophilic aromatic substitution of benzoic acid to produce m-nitrobenzoic acid

_____/30

Experiment Title: (0/30 points)

Date: (0/30 points)

Laboratory Partners: (0/30 points)

Goals: (1/30 points)

Procedure changes: Describe any changes performed in the original procedure. Describe as well what was in your original procedure. (1/30 points)

Chemical Overal Reaction Reactions Use ChemDraw (1.5 /30 points)

Reaction Mechanism Use ChemDraw, arrows can be hand drawn (2.5 /30 points)

Observations: No data presentation; Please refer to page 35 in your lab book for examples of what (and how) to report your observations; Include any observation you feel pertinent about your experiment, specially the ones that may have an effect on your obtained results. (1.5/30 points)

Calculation: Use the amount of benzoic acid, and nitric acid you started with. Calculate the limiting reagent, theoretical yield and reaction yield. Show all calculations. Show a neat work. (1.5 /30 points)

Results: Report all of your data acquired here, no data discussion. Use the data collected during your experiment; they will be compared to the data you left behind for your TAs. Report all your data in a clear way. Report the MP for your product; include a copy of your thermometer calibration (first lab) and BE SPECIFIC ON WHICH INSTRUMENT YOU USE FOR YOUR MEASUREMENTS. Include a copy of your recorded IR and 1H-NMR spectra. For the 1H-NMR mark sets of peaks and relate to peaks in molecule o m-nitrobenzoic acid. DO NOT DISCUSS YOUR spectra here!. When using tables and graphs, you need legend; be clear on which calculations you are showing and what your numbers represent. Any chemical structure must be done using ChemDraw or it will not be given credit. (5/30 points)

TAs: 1.0 point for data clear presented; give 1.0 points for MP, 1 point for IR and 2.0 for 1H-NMR of product including preference to the peaks on spectra;

Discussion: Discussion is dissertative. Use “It” instead of “I, She/He” when writing the discussion.Your discussion shall explain (not necessarily in the sequence below):

· What is aromatic substitution? What is the characteristic mechanism for aromatic substitution?

· What is the electrophile and the nucleophile species in the nitration of aromatic substitution reactions?

· How activating groups and deactivating groups affect the reactivity of aromatic compounds? How activating and deactivating groups direct the incoming substituent into the ortho, para or meta position of the ring? What is the role played by of carboxylic acid in benzoic acid?

· What is the function of nitrating mixture?

· Why temperature must be controlled in this reaction?

· Summarize your MP findings. Is your product pure? (DO NOT FORGET TO CORRECT TEMPERATURE, KEEP YOUR ORIGINAL MP RECORD AND YOUR CORRECT MP IN MIND WHEN DISCUSSING YOUR DATA)

· Analyze your 1H-NMR. Does your spectrum support your MP data?

· Would you expect that your 1H-NMR can differentiate between pure o-nitrobenzoic acid, m-nitrobenzoic acid and p-nitrobenzoic acid?

· What is the yield for the reaction? Is this a real yield for the reaction (if your product is impure, part of the mass you are calculating is not product of interest).

· Discuss the problems you faced in this experiment; what did you learned and what would you do different? (10/30 points)

Conclusion: what is your conclusion (what did you learned from your experiment?). Be sure your conclusion will correlate the goals you have for your experiment. It is fine to break your conclusion in parts. (2 /30 points)

References: Cite books, procedures and any other source used for writing your lab report in ACS manner; (2/30 points)

Discretionary: (2/30 points)

Part II

Multi-step synthesis part II: Fisher Esterification of m-nitrobenzoic acid to produce methyl m-nitrobenzoate;

Experiment Title: (0/30 points)

Date Performed: (0/30 points)

Laboratory Partners: (0/30 points)

Goals: (1/30 points)

Procedure change: Describe any changes performed in the original procedure. Describe as well what was in your original procedure. (1/30 points)

Chemical Overal Reaction Reactions Use ChemDraw (1.5 /30 points)

Reaction Mechanism Use ChemDraw (2.5 /30 points)

Observations: No data presentation; Please refer to page 35 in your lab book for examples of what (and how) to report your observations; Include any observation you feel pertinent about your experiment, specially the ones that may have an effect on your obtained results. (1.5/30 points)

Calculation: Use the amount of m-nitrobenzoic aci, and methanol you started with. Calculate the limiting reagent, theoretical yield and reaction yield. Look back at your Part I reaction yield and calculate the yield for the multi-step synthesis. Your handout will show you how to do the calculations. Show all calculations. Show a neat work. (1.5 /30 points)

Results: Report all of your data acquired here, no data discussion. Use the data collected during your experiment; they will be compared to the data you left behind for your TAs. Report all your data in a clear way. Report the MP for your product; Include a copy of your recorded IR and 1H-NMR spectra, For the 1H-NMR, mark sets of peaks and relate to peaks in molecule o methyl -m-nitrobenzoate, but DO NOT DISCUSS YOUR NMR here!. When using tables and graphs need legend; be clear on which calculations you are showing and what your numbers represent. Any chemical structure must be done using ChemDraw or it will not be given credit. (5/30 points)

TAs: 1 point for data clear presented; give 1 point for MP ,I point for IR and 2 points for the 1H-NMR. Data shall match the data left behind or no credit will be given;

Discussion: Discussion is dissertative. Use “It” instead of “I, She/He” when writing the discussion.Your discussion shall explain (not necessarily in the sequence below):

**Note:The part one reaction focused on the aromatic ring. Here, the reaction happens on the carbonyl group (carboxylic acid group). Carbonyl compounds can be divided into two class of compounds, each of them with their characteristic mechanism.

· Which carbonyl compounds belong to class I carbonyl compounds and which carbonyl compounds belong to class II compounds? What is the characteristic reaction mechanism for each of the carbonyl class compounds?

· What is Fisher Esterification? What is the function of the acid in this reaction?

· Summarize your MP data. Compare your values (original recording and corrected) to the real MP for methyl-m-nitrobenzoate and indicate if your product is or not pure

· Would 1H-NMR be able to indicate if your final reaction product is impure with m-nitrobenzoic acid (or benzoic acid from your first reaction?).

· Analyze your 1H-NMR. Does your data reinforce your MP data?

· What can be said of your reaction yield? What can be said of your multi-step reaction yield? Is this a real yield? If not, what do you think it needs to be done for calculating the real yield?

· Discuss the problems you faced in this experiment, specially the ones that can affect your yield; what did you learned and what would you do different? (10/30 points)

Conclusion: what is your conclusion (what did you learned from your experiment?). Be sure your conclusion will correlate the goals you have for your experiment. It is fine to break your conclusion in parts. (2 /30 points)

References: Cite books, procedures and any other source used for writing your lab report in ACS manner; (2/30 points)

Discretionary: (2/30 points)