Chemistry 216Acetylation of Aniline Worksheet

Instructions:1. Download this word document.2. Fill in your answers in italic font below the corresponding question. Answers should be brief and concise. Your responses should be grammatically correct. Be sure to use spell checker.3. You are to complete the following on your own. All responses should be written in your own words and not those of other students in your section. Unauthorized collaboration on this assignment will result in a zero. Plagiarism will result in a zero for the assignment.4. This worksheet is due 3 days after the completion of the experiment, to your gsi, at the start of your lab session.

Your Name:

1. Enter the mass of the products for part 1 & 2 and the final % yield for each reaction in the table below. If you were unable to purify your product, crude yield may be reported instead. If you obtained no product your percent yield will be zero. If you recovered only starting material make a note of that. Remember that your starting material doesnt just disappear! If your reaction didnt work you either have unreacted starting material or have formed an undesired product. Whatever you obtained you should be able to isolate and characterize it so that you can figure out what happened. Note: your GSI will also check your % yield calculations in your lab notebook.

ProductMass% Yield

Part 1: Acetanilide

Part 2: Unknown

2. Describe in your own words what happens to the reaction mixture (i.e. what do you visibly observe), and to the aniline molecule on the microscopic level, as concentrated hydrochloric acid is added.

3. Why is sodium acetate used? What would happen if NaOH was used instead (there are two possible answers for what happens with NaOH and you only need to provide one)?

4. Which unknown compound did you have? Explain your conclusion using the data you obtained in lab (TLC, mp, Bielstein, Infrared spectroscopy).

5. Aniline is not water-soluble, but the reaction solvent is water. The reaction procedure gets around this problem by using HCl to protonate aniline and increase its solubility in water. Propose two other strategies that could be used for the acetylation of aniline under conditions where the reactants are soluble in the reaction medium. Find at least one source of information that supports your explanation and cite it below. You should be able to defend whether it is a reputable source of information.

6. How does the Infrared spectrum of your unknown amine compare to that of aniline? How does the spectrum of your unknown acetamide product compare to that of acetanilide? Be specific and indicate which peaks differ (including the cm-1 position on the spectrum and the functional group it corresponds to). See the Infrared Spectroscopy table and tutorial on CTools for help identifying peaks in your spectrum.

To be completed by GSI:Acetylation Experiment Points Summary

AssignmentTotalSection Average

Worksheet

Notebook pages

GSI points P1

GSI points P2

Comments on GSI points: