Practicing Success

Target Exam

CUET

Subject

Chemistry

Chapter

Organic: Alcohols, Phenols and Ethers

Question:

Answer the question on basis of passage given below:

Alcohols and phenol are formed when a hydrogen atom in a hydrocarbon, aliphatic and aromatic respectively, is replaced by -OH group. The substitution of a hydrogen atom in a hydrocarbon by an alkoxy or aryloxy group forms ethers.

Alcohols and phenol consist of two part, an alkyl/aryl group and a hydroxyl group. The properties of alcohols and phenols are primarily due to the hydroxyl group. The nature of alkyl and aryl groups simply modify these properties. Alcohol react both as nucleophiles and electrophiles whereas in phenols, the reactions that take place on the aromatic ring are electrophilic subtitution reactions.

Aspirin is an acetylation product of:

Options:

o-Dihydroxybenzoic acid

o-Hydroxybenzoic acid

m-Hydrxoybenzoic acid

p-Dihydroxybenzene

Correct Answer:

o-Hydroxybenzoic acid

Explanation:

The correct answer is option 2. o-Hydroxybenzoic acid.

Aspirin is a NSAID (non-steroidal anti-inflammatory drug), and sometimes it is synthesized from modification of other related compounds called salicylates.

It is the acetylated form of salicylic acid, with which it was first extracted from a willow bark. Willow bark had long been known to ease pain, reduce fever, and reduce inflammation, and ASA is one of the reasons.

Let us look at the mechanism of aspirin:

Salicylic acid (O-hydroxybenzoic acid) is a monohydroxybenzoic acid that is a benzoic acid with hydroxyl group at the ortho position. It contains both the organic acid and the phenolic functional groups and is capable of two different esterification reactions, depending on which functional group reacts.

With an excess of acetic anhydride in the presence of a catalyst (sulphuric acid) to produce the acetylsalicylic acid.

After the reaction takes place, water is added to destroy the excess acetic anhydride present and cause the product to crystallize.

Synthesis of Aspirin: