Practicing Success

Target Exam

CUET

Subject

Chemistry

Chapter

Organic: Alcohols, Phenols and Ethers

Question:

An organic compound (A) with molecular formula C6H6O gives a characteristic colour with aqueous solution. When (A) is treated with CO2 and NaOH at 410K under pressure, it gives compound (B) which upon acidification gives compound (C). Compound (C) reacts with acetyl chloride to give (D) which is a popular pain killer.  

Identify the product (D)?

Options:

Salicylic acid 

Aspirin 

Acetyl salicylate 

None of the above 

Correct Answer:

Aspirin 

Explanation:

(i) Since, compound (A) with molecular formula C6H6O gives characteristic colour with FeCl3, therefore (A) must be a phenol.
(ii) Since compound (A), i.e., phenol reacts with CO2 and NaOH under pressure (i.e., Kolbe's reaction) to give compound (B) which on acidification gives compound (C), therefore, (B) must be sodium salicylate and (C) must be salicylic acid.
(iii) Since (C) reacts with acetyl chloride to form a popular pain killer (D), therefore (D) must be aspirin.
(iv) All the above reactions may be explained as follows: