Question

I am writing up a lab report on the synthesis of phenacetin from para-acetamidophenol,(using sodium ethoxide and ethyl iodide as catalyst) and in need of the following;

-Observations during the experiment(very important)

-Sources of errors

-Improvements

-Comment on the appearance of product formed.

Thank you.

Answer 1

IR assignments
1659cm-1           Amide C=O stretching vib.
837cm-1           Aromatic C-H bending vib. (2 adj H atoms)
1611,1557,1509,1447cm-1   Aromatic C=C stretching vib.
1369cm-1           Alkane C-H bending vibrations
3278cm-1           Amide N-H stretching vib.

1H NMR assignments
1.374    (t, 3H, 3H-1), 1.634 (s, 2H), 2.124 (s, 3H, 3H-6), 3.982 (q, 2H, 2H-2), 6.819 (m, 2H, 2H-4), 7.174 (m, 1H, 1H-5), 7.336 (m, 2H, 2H-3)

13C NMR assignments
15.128 (1C, R-CH3, 1), 24.554 (1C, R-CH3, 8), 63.997 (1C, R1-CH2-O-R, 7), 115.036 (2C, aromatic 1H, 4 & 5), 131.199 (1C, aromatic 0H, 3), 156.099 (1C, aromatic 0H, 6), 168.753 (1C, R-NH-(C=O)-R1, 2).

Proper care for reflux condensation and crystalisation should be followed otherwise error will arise.

Comment

It is in this writers opinion that to call acetaminophen or phenacetin a non-steroidal anti-inflammatory drug (NSAID) because it is a not an opioid analgesic is as incorrect as calling Welbutrin a selective serotonin reuptake inhibitor (SSRI) because it is not a tricylic or monoamine oxidase inhibitor (MAOI) antidepressant!