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(Solved) CH 338 Winter 2017 Make up lab. Acetylation of Ferrocene In this experiment, we will perform the Friedel-Crafts acetylation of ferrocene. We will be...


There are tables in question 3, I believe 3 of them. Want to use this as a guide to help me for my final but I don't know how to fill in these tables. Any help would be a great support, thank you. Question and attachment follow: 


3. Analyze the 1 H and 13C NMR spectra of the acetylferrocene product. Fill in the tables below, from high to low chemical shift. Clearly show your 1 H and 13C assignments using the structures below (use the letters/numbers from the tables)

CH 338 Winter 2017
Make up lab. Acetylation of Ferrocene In this experiment, we will perform the Friedel-Crafts acetylation of ferrocene. We will be
following the procedure on pg. 225 – 230 of the “Green Organic Chemistry” textbook (Experiment 18 –
posted on Canvas). Be sure to acquire an IR spectrum of your product before leaving lab.
O
Fe O
O H3PO4 O
Fe Pre-Lab Notebook Entries [25 points]
Follow the general format. Experimental Notebook Entries [25 points]
Follow the general format. Post-Lab Report
To be handed in: Copies of your notebook pages + your IR spectrum + answers to the Post-Lab
Questions. 1 CH 338
Post-Lab Questions Winter 2017 1. The 1H and 13C NMR spectra of ferrocene are included in this handout. Given that the two isomers
shown below are at energy minima (and are within 1 kcal / mol of each other), what do the NMR spectra
tell you about the dynamic behavior of ferrocene? Explain.
[10 points] 2. Compare the IR spectra of ferrocene and your product. Which peak(s) in the product are important for
characterization of the product? [5 points] 2 CH 338
Winter 2017
1
13
3. Analyze the H and C NMR spectra of the acetylferrocene product. Fill in the tables below, from
high to low chemical shift. Clearly show your 1H and 13C assignments using the structures below (use the
letters/numbers from the tables).
[15 points]
1
H NMR
integral a
b
c
d
13 C NMR 1
2
3
4
5
6
1 H assignments: 13 C assignments: 3 CH 338
Winter 2017
4. Instead of heating the reaction with a water bath, someone decided to find out what would happen if a
heating mantle were used instead. So instead of conducting the reaction at ~ 90 oC, this reaction was
heated at reflux (boiling point of acetic anhydride is 139 oC). From this reaction was isolated a major
product that is not acetylferrocene. Based on the IR spectrum, NMR spectra and mass spectrum (the
molecular ion is at 270) identify this compound and clearly explain how you arrived at this structure. The
NMR spectra are posted included in this handout. [10 points] 5. For the mass spectrum of the compound in #4, justify the presence and the relative intensity of the
following peaks:
(the peak at m/z = 270 has a relative intensity of 100) [10 points]
(a) m/z = 268 (relative intensity = 6.8%)
(b) m/z = 271 (relative intensity = 17.5%)
_________________
100 points total
4 1 CH 338
H NMR spectrum of Ferrocene (300 MHz, CDCl3) Winter 2017 Peak Listing: δ 4.20 5 13 CH 338
C NMR spectrum of Ferrocene (75 MHz, CDCl3) Winter 2017 Peak Listing: δ 68.21 6 1 CH 338
H NMR spectrum of Acetylferrocene (300 MHz, CDCl3) Winter 2017 Peak Listing: δ 4.76, 4.50, 4.20, 2.39 7 13 CH 338
C NMR spectrum of Acetylferrocene (75 MHz, CDCl3) Winter 2017 Peak Listing: δ 202.35, 79.46, 72.59, 70.09, 69.83, 27.69 8 1 CH 338
H NMR spectrum for Question #4 (300 MHz, CDCl3) Winter 2017 Peak Listing: δ 4.72, 4.46, 2.30 9 13 CH 338
C NMR spectrum for Question #4 (75 MHz, CDCl3) Winter 2017 Peak Listing: δ 201.31, 80.85, 73.80, 71.16, 27.86 10

 


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