Chemistry 216

Acetylation 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.
Product
Part 1: Acetanilide

Mass

% Yield

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
Assignment
Total
Section
Average
Worksheet
Notebook pages
GSI points P1
GSI points P2
Comments on GSI points: