So this is my TLC from an experiment I did where I prepared Phenacetin from acet

Question

So this is my TLC from an experiment I did where I prepared Phenacetin from acetaminophen and ethyl iodide. My question is 1) what do each of these 5 spots represent. And am I missing a spot that is supposed to be there but isn't?
Question 2) Does the TLC plate indicate that acetaminophen was at least partially removed from the reaction mixture between steps 4 and 9 during the procedure?

My TLC plate: Line 1: step 4 Line 2: authentic acetaminophen Line 3: step 9
Details about the experiment:
Procedure:

Explanation / Answer

Analysis by tlc

1) Spots on tlc plate

first line : two spots, bottom spot is acetaminophen, top spot is product phenacetin

Second line : one spot, pure scetaminophen

third line : two spots, bottom spot is acetaminophen, top spot is product phenacetin

Polarity of compounds follow the order (decreasing) : acetaminophen > phenacetin > ethyl iodide

Ethyl iodide is least polar and would If present be seen close to solvent front. Since we do not see that in line 1 and line 2, we can assume no ethyl iodide is left in the reaction mixture.

2) step 4 is reaction mixture monitoring.

Aliquot of reaction mixture when spotted on the tlc plate, gave two spot and shown on line 1.

when separation of acetaminophen by phenoxide formation was done in step 8, and then organic layer from step 8 was dried in step 9 and spotted on tlc plate, we see two spots similar to as seen in line 1.

Thus we still have acetaminophen left in the mixture along with the product. However, since NaOH is a strong base, we can say some of acetaminophen is been removed by the step 8 from the mixture.

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