What is a Reaction that you would expect when acetylsalicylic acid (aspirin) is heated in the presence of a CONCENTRATED acid?
Thanks in advance!
I am far from an organic chemist but I would think it would hydrolyze to form salicylic acid and acetic acid. I don't know if the SA would decompose after that or not.
When acetylsalicylic acid (aspirin) is heated in the presence of a concentrated acid, such as sulfuric acid or hydrochloric acid, a reaction known as ester hydrolysis occurs. Here are the step-by-step details of the reaction:
1. The concentrated acid protonates the carbonyl oxygen atom of acetylsalicylic acid, forming a positively charged carbon (carbocation) and an acetate ion (conjugate base of the acid).
2. The carbocation undergoes nucleophilic attack by one of the lone pairs on the oxygen atom of water molecules present in the acid solution. This attack leads to the formation of a new carbon-oxygen bond.
3. The attack of water also breaks the ester bond between the carbonyl carbon and the salicylate group, resulting in the formation of salicylic acid.
4. Another water molecule can attack the positively charged carbon, leading to the formation of acetic acid.
Overall, the reaction can be summarized as follows:
Acetylsalicylic acid + Water → Salicylic acid + Acetic acid
Note that heating the reaction mixture is essential to speed up the reaction rate, and using a concentrated acid increases the acidic strength, facilitating protonation of the carbonyl oxygen and enhancing the reaction's progress.
When acetylsalicylic acid (aspirin) is heated in the presence of a concentrated acid, a reaction known as hydrolysis occurs. The concentrated acid breaks down the ester bond present in acetylsalicylic acid, resulting in the formation of salicylic acid and acetic acid as products.
To understand this reaction, it is important to know the chemical structure of acetylsalicylic acid. Acetylsalicylic acid contains an ester functional group (-COO-), which is susceptible to hydrolysis when subjected to acids. In the presence of concentrated acid, the ester bond undergoes cleavage, forming the corresponding carboxylic acid and alcohol.
To confirm this reaction, you can perform the following steps:
1. Take a small amount of acetylsalicylic acid (aspirin) and place it in a heat-resistant container, such as a test tube.
2. Add a few drops of a concentrated acid, such as sulfuric acid or hydrochloric acid, to the test tube.
3. Gently heat the mixture using a Bunsen burner or a heating source.
4. Observe any changes in the appearance or smell of the mixture.
5. After some time, compare the resulting mixture to the original acetylsalicylic acid.
You would expect to see the formation of salicylic acid and acetic acid, along with changes in the appearance and smell of the mixture. It is important to note that these reactions should be performed under appropriate laboratory conditions and precautions.