Question

Which of the following compounds is aspirin?
(A) Methyl salicylate
(B) Acetyl salicylic acid
(C) Phenyl salicylate
(D) Salicylic acid

Answer 1

Hint: (1) Aspirin is an analgesic which means that it can reduce pain without causing any kind of mental confusion or disorder of the nervous system. In other words, it is a neurologically active drug.
(2) The IUPAC name of aspirin is 2-acetoxybenzoic acid.

Complete step by step answer: According to the IUPAC nomenclature of aromatic compounds, the parent hydrocarbon is benzene and when it is monosubstituted by the carboxyl functional group \[\left( {{\text{COOH}}} \right)\] , it is named as benzoic acid. Also, for disubstituted aromatic compounds, the principal group on the ring is given the number 1.

Since the IUPAC name of aspirin is 2-acetoxybenzoic acid, let us first see its structure.

From the structure of aspirin, we can see that it is an acetyl derivative of salicylic acid. It is formed when salicylic acid (2-hydroxybenzoic acid) is treated with acetic anhydride. During this reaction, the hydroxyl group of the salicylic acid$\left( {{\text{OH}}} \right)$ is converted into an ester group $\left( {{\text{OCOC}}{{\text{H}}_{\text{3}}}} \right)$. Acetic acid is a byproduct of the reaction. The formation of aspirin is shown below.

Thus, aspirin is also called acetyl salicylic acid.
So, option B is correct.
Since methyl salicylate is the methyl ester of salicylic acid, its structure will be:

Hence, it does not represent the structure of 2-acetoxybenzoic acid or aspirin. Thus, option A is not correct.
Since phenyl salicylate is the phenyl ester of salicylic acid, its structure will be:

Hence, it does not represent the structure of aspirin or 2-acetoxybenzoic acid. Thus, option C is also not correct.
Lastly, salicylic acid is 2-hydroxybenzoic acid which is used for the synthesis of aspirin. So, it cannot be aspirin itself. Its structure is shown below.

Hence, option D is also not correct.
Note: Aspirin is known to inhibit the synthesis of prostaglandins which causes pain in the tissues. It is also widely used in preventing heart attacks because of its anti-blood clotting action. However, it has some drawbacks too. It is considered to be toxic to liver and sometimes also leads to bleeding from the stomach. Because of these drawbacks, some other analgesics like ibuprofen, naproxen etc. are used as alternatives to aspirin.