**I decided to change my idea for this assignment to something more technical and

related to my discipline.**

Abigael Gunther Commented [AR1]: Professor Akbari mentioned in his

55 Hemenway St. screencast that since your name closes the letter, you
dont have to include it in your return address.
Boston, MA 02115

May 18, 2017

Dr. Brian Fulton

Lecturer Commented [AR2]: Is he also a professor? What
Northeastern University department?

Hurtig Hall (102)

334 Huntington Ave
Boston, MA, 02115

Dear Professor Fulton,

I am writing to propose an alternative laboratory protocol to be used by upper-

level undergraduate students for the Lewis Acid Catalyzed Friedel-Crafts Acetylation of
Ferrocene in the Chemical Synthesis and Characterization course.
As a current student in this course, I have a personal appreciation of the Commented [AR3]: This successfully establishes you as
experience level held by my classmates and myself. Throughout the course we have knowledgeable and personally invested.

been exposed to many new organic chemistry techniques, but we found the second
experiment to be lacking in direction. Commented [AR4]: Who wrote it? This may come
I have taken the liberty of compiling a detailed protocol for this experiment that across as insulting if Dr. Fulton himself wrote it.

more clearly incorporates the procedure of Tappe, K. and Knochel, P. Tetrahedron:
Asymmetry 2004, 15, 91-102 and your desired modifications. I request you examine
and consider the integration of this document for future students of this seminar. I think
you will find it follows a clear chronological order and contains a detailed description of
the more advanced techniques, while still being challenging enough to maintain the
advanced level of the course.
You may contact me any time by email at gunther.a@husky.neu.edu, or by
telephone at (832) 523-9336 to discuss my proposal.
Thank you for your time.
Commented [AR5]: You just mentioned that you are a
student in this class. What makes you more qualified to
write this protocol than your professor or TA? For
example, you could mention that you have performed
this experiment and thus you have specific tips and tricks
that you can share with fellow students.
Commented [AR6]: This statement could also be useful
in establishing your credibility in writing this document.
You have a particular understanding of what knowledge
you already have and what knowledge would be useful to
have as a student performing this experiment.

Regards,

Abigael Gunther

Enc. (2)
Lewis Acid Catalyzed Friedel Crafts Acetylation of Ferrocene
To a 25 mL round bottom flask, add 236 mg (1.77 mmol) of aluminum (III) chloride and
a magnetic stirrer. Cover flask with a plastic stopper.
To avoid water from the atmosphere interfering with
the reaction, all steps going forward must be done
under a nitrogen atmosphere. To do so: Fit the plastic
body of a syringe into thick-walled rubber tubing.
Secure an unfilled balloon onto the tubing with a
rubber band. Connect the syringe to a flow of nitrogen
(typically found in the fume hood) and fill the balloon
with nitrogen. To avoid loss of nitrogen to air, quickly
attach a needle to the syringe, then pierce the plastic
stopper on top of the round bottom flask.
The final set-up should appear similar to the image on
the right.
Note: the absence of water up until the point of
quenching is critical. If the balloon method was
performed incorrectly the reaction will not produce the
correct product.
Add 0.127 mL (1.79 mmol) of acetyl chloride and 2 mL
of DCM via syringe. Allow the reaction to stand and
stir at room temperature for 30 minutes.
While waiting, add 291 mg of ferrocene to a 5 mL
conical flask. Set up another balloon filled with
nitrogen (following the same method as described above) and attach to the flask. Add 2
mL of DCM via syringe. Allow reaction to sit in an ice bath for at least 10 minutes, or
until the aluminum chloride/acetyl chloride/DCM solution has stirred for 30 minutes.
Add the cold ferrocene/DCM mixture to the aluminum chloride/acetyl chloride/DCM
mixture in the round bottom flask via (the same?) needle and syringe. Allow the
reaction to stir for an hour at room temperature.
Quench the solution with 5 mL ice-cold water, then remove the balloon apparatus.
Commented [AR7]: I have made lots of comments
below. They definitely reflect my ignorance of chemistry,
so I trust your best judgement on whether they are
applicable to students in this class or not!
Commented [AR8]: Would it be helpful to have a list of
supplies/reagents necessary so you can have those
ready?
Commented [AR9]: This diagram is very helpful
because it gives students a reference with which to
compare their set-up.
Commented [AR10]: This feels a bit awkward to me.
Maybe you could rephrase to something like To avoid
interference from atmospheric water, a nitrogen
atmosphere must be established.
Commented [AR11]: This feels a little wordy to me.
Perhaps you could simplify it to Connect the syringe to a
nitrogen source
Commented [AR12]: How? Using the syringe?
Commented [AR13]: This is helpful! It shows that you
have done this experiment before and have some tips and
tricks you can share with future students. As a side note,
is there a way to tell if you have set it up correctly at this
point? Maybe not, but it would be helpful to troubleshoot
it now if possible.
Commented [AR14]: To the flask? With the same
syringe from before?
Commented [AR15]: Is this a standard abbreviation?
Will students at this level know what this is?
Commented [AR16]: Are these times supposed to be
equivalent? Is one of these optimal?
 The next step is to separate the phases using a separation Commented [AR17]: There seem to be different
funnel. To prevent spilling it is useful to use a funnel to parts/sections to this experiment. Would it be helpful to
add subheadings?
transfer solutions. Set up a standard separation funnel
Commented [AR18]: More tips! It would be neat if
with a clean beaker underneath the outlet, like the image you could find a way to section off your tips so they stood
on the left. Once the washing liquid is added, extraction out visually.
occurs by ensuring the stopcock is closed and the inverted
stopper is in place. Remove from the stand and invert the
funnel. Shake the funnel vigorously for a few seconds and
then slowly open the stopcock to vent pressure buildup.
Take care to open the stopcock facing away from you.
Shake and vent a second time.

Note: Separatory funnels separate solution phases based on

density. The low density liquid is on top and high density
liquid is on the bottom. Depending on what is being used to
wash the solution, the organic layer can alternate between
being the top or bottom layer. Commented [AR19]: Will there be a result expected for
this lab specifically?

Pour the solution into the separatory funnel and wash three times with 10 mL of DCM.
DCM is less dense than the organic layer so it will separate onto the top. After each
wash, filter out the organic layer into the beaker on the bottom. By the third wash the Commented [AR20]: How?
separatory funnel should only contain the aqueous layer. Remove this and then discard. Commented [AR21]: Which part am I discarding?

Return the organic layer to the separatory funnel, then wash with 10 mL of a saturated
K2CO3 solution. The organic layer is now on top. Filter out the K2CO3 solution. Repeat Commented [AR22]: How?
this process with 10 mL of water. Then repeat with 10 mL of brine.

Collect the organic layer in a small beaker and dry over MgSO4. After a few minutes,
remove the magnesium sulfate with vacuum filtration. You should be left with an orange
solution that contains the crude acetyl ferrocene product. Reduce the product in the
rotary evaporator and then leave overnight to fully dry.

The following morning, test the purity of the product by 1H-NMR,

IR, and TLC. Dissolve 2 mg of the product with 0.7 mL deuterated
chloroform in a 20 mL beaker. Transfer this by Pasteur pipette
into an NMR tube. Operating the complex 1H-NMR and IR
machines is not a part of this course. Ask your professor to run
perform these test. Commented [AR23]: Perhaps include this information
at the beginning of the paragraph?

To run the TLC, dissolve a minimal amount of your product (A),

known acetyl ferrocene (B), and known diacetyl ferrocene (C) into
a test tube with a few mL of DCM. Spot each solution into their
corresponding columns on the plate. Make a tentative
identification of the products by using a mixture of 1:9 ethyl
acetate:hexane as the mobile phase. Your product and the known
acetyl ferrocene should elute to the same spot.

Confirm the product with your 1H-NMR and IR results.

Dear Abigael,

I have taken a few chemistry classes as a BNS major, so I completely understand

that the protocols are not always the most helpful that they could be! While I empathize
with your commentary that the current lab protocol was not particularly helpful, I
would be cautious with your wording in your cover letter. I mentioned in my comments
that, depending on who wrote the protocol, commenting on its failures may come across
as attacking. As a student, you have a unique perspective on how best to present a lab
protocol to other students taking this course. I think you could use this to your
advantage and include your own personal tips and tricks you have learned. This could
help you establish your authority in amending a document that was written by
professors, TAs, and the original authors of the protocol without accidentally causing
offense.
I made many comments on the document itself asking for clarification on a few
steps. I hope that was not intimidating! Most of them are reflective of my lack of
chemistry knowledge, and I am sure you will use good judgement in determining which
ones are relevant to students in this course. I thought the use of images to demonstrate
proper equipment set-up was particularly useful. Words can easily be misread or
misinterpreted, so it is helpful to have a picture to refer to. You could possibly make
these images larger or use color or arrows to highlight important pieces to highlight the
most important parts. I also like how you incorporated tips, tricks, and relevant
explanations of why certain steps are important. I think you could make these notes
stand out visually (for example, offsetting them from the rest of the text) to draw more
attention to them. Finally, I suggested adding a list of supplies and reagents to the
beginning of the protocol and breaking the protocol into sections with subheadings,
which could make the document easier to use for the reader.
I hope these comments are easy to understand and are helpful to you. I am
looking forward to the finished product.

Best,
Amber