Question

What is the product 'Z' in the given sequence of reactions?

• A. A phenyl ether with an ortho -OH group
• B. A phenyl ether with an ortho -COOH group
• C. A phenyl ether with a meta -OH group
• D. A phenyl ether with a para -OH group

Hint:

Remember the key reactions of phenol: - \textbf{Kolbe-Schmitt Reaction:} Phenol + NaOH, then CO\(_2\), then H\(^+\) \(\rightarrow\) Salicylic acid (o-hydroxybenzoic acid). - \textbf{Reimer-Tiemann Reaction:} Phenol + CHCl\(_3\)/NaOH \(\rightarrow\) Salicylaldehyde (o-hydroxybenzaldehyde). - \textbf{Acetylation:} Phenol + Acetic Anhydride \(\rightarrow\) Phenyl acetate. The reaction of Salicylic acid with acetic anhydride gives Aspirin.

Answer 1

The Correct Option is B

To determine the product 'Z' in the given sequence of reactions, let's analyze each step:

1. Formation of Compound X:

   Aniline reacts with NaNO₂/HCl at 273-278K to form a diazonium salt. When this is treated with water (H₂O, warm), it undergoes hydrolysis to form phenol. Hence, compound X is phenol.

2. Formation of Compound Y:

   Phenol, when reacted with NaOH followed by CO₂ and then treated with an acid (H⁺), undergoes a Kolbe-Schmitt reaction, which converts the phenolic -OH group into an ortho-carboxylic acid group. Therefore, compound Y is salicylic acid (ortho-hydroxybenzoic acid).

3. Formation of Product Z:

   Salicylic acid is then reacted with acetic anhydride (CH₃CO)₂O, where the -OH group of the salicylic acid reacts with acetic anhydride to form the ester, acetylsalicylic acid (also known as aspirin). Therefore, compound Z is a phenyl ether with an ortho -COOH group.

Thus, the final product 'Z' is a phenyl ether with an ortho -COOH group.

Correct Answer: A phenyl ether with an ortho -COOH group.