5. Below are structures of common aspirin substitutes. Why do ibuprofen and napr

Question

5. Below are structures of common aspirin substitutes. Why do ibuprofen and naproxen not give a positive test with 1% iron(III) chloride? Why does acetaminophen give a positive test? CH 3 CH-CH-CH3 CHs CH-COOH CH3O OH CH-COOH CH3 Acetaminopben Ibuprofen Naproxen 6. Bottles containing old aspirin tablets often smell of vinegar. The presence of what chemical causes this smel? How does this chemical form? 7. You may have observed that not all of the commercial aspirin dissolved in the added water would account for the undissolved material?

Explanation / Answer

5)Ferric chloride test is given by phenols and enols only.

Acetaminophen has a phenolic Oh group thus gives positive Fe(III) Cl3 test while the other two structures do not hvae the phenolic group thus negative FeCL3 test.

6)Aspirin is acetyl salicylic acid .with the -COOH and -OCOCH3 groups on ortho positions of benzene ring.

When it is kept for longer periods , the -OCOCH3 undergoes hydrolysis slowly giving acetic acid and -Oh groups.

The acetic acid formed is responsible for the vinegar smell.

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