These are the experiments I did in lab today... 73 was done successfully and the

Question

These are the experiments I did in lab today... 73 was done successfully and then we used that to do the next one. When I did the second part when boiling it , it turned a darker orange / brownish color then after two hours I added the water and it turned black! My friends when boiling turned a nice light orange then stayed that way when adding the water.
ooo TFW 7:10 PM 86%, books.google.com Sign in News Gmail More Add to my library Write review Page 530 E73. p Acetamidophenol from p-Amino- phenol: Preparation of Tylenol pH-about 5 paminophenol eg- Tylenol Scale: 1.1 gram (0.010 mole) of paminophenol. Place 1.1 grams (0.010 mole) of paminophenol (Note 1) in a 50-mL Erlenmeyer flask. Tothis flask, add 10 mLof water and 0.9 mL (0.011 mole) of concentrated HCI. Swirl the flask to dissolve the amino Why does the aminophenol phenol (Note 2) Prepare a solution of 1.0 grams (0.012 mole) of anhydrous so- dium acetate (Note S) in 6 mLof water. Tothe solution of paminophenolin Ha.add ilmLO2 grams. 0012 mole) of acetic anhydride, Swirl the mixture to dissolve almost all of the acetic anhydride, add the solution of sodium acetate, swirl the mixture to mix it thoroughly, and set it aside for crystallization (Note 4). Collect the product by suction filtration, and wash it withalittle cold water. Yeld: about grams about 75%. l. Commercial paminophenol is often quite dark It can be deaned up somewhat by suspending itin about twice itsvolume ofmethanol and then recovering it by suction filtration. the solution is too highly colored. add as much decolorizing car.

Explanation / Answer

First reaction is N-acylation

and Second reaction is O-Alkylation.

In first reaction you used acetic anhydride. But in second reaction you used ethyl bromide.

It contains bromin. When you add water it is possible in the reaction some side reaction liberates Br from Ethyl bromide. Such as Ehtyl bromide and NaOH gives Ethanol and Bromine.

Other possibility is that reagent you used may be not good it continas excess dissolved bromine.

Or heating is not uniform.

The dark colouration is because of Bromine.

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