Question:medium

Write the structure of zwitter ion of sulfanilic acid. Write the reaction between benzene diazonium chloride and phenol in alkaline medium.

Show Hint

Coupling with phenol happens at the para-position. If the para-position is blocked, it happens at the ortho-position.
Show Solution

Solution and Explanation

Step 1: Understanding the Concept:
A zwitterion is a dipolar ion formed by the internal transfer of a proton from an acidic group to a basic group within the same molecule.
Step 3: Detailed Explanation:
Sulfanilic acid (\(NH_2-C_6H_4-SO_3H\)) contains a basic amino group (\(-NH_2\)) and an acidic sulfonic acid group (\(-SO_3H\)).
The proton (\(H^+\)) from the \(-SO_3H\) group is transferred to the \(-NH_2\) group.
This results in a structure where the nitrogen carries a positive charge and the sulfonate group carries a negative charge.
Structure:
\[ \text{A benzene ring with } ^+NH_3 \text{ at one end and } SO_3^- \text{ at the para position.} \]
Step 4: Final Answer:
The zwitterion form of sulfanilic acid is \(^+NH_3-C_6H_4-SO_3^-\).

Step 1: Understanding the Concept:
Azo coupling is an electrophilic aromatic substitution reaction where a diazonium cation reacts with an activated aromatic ring (like phenol).
Step 3: Detailed Explanation:
Benzene diazonium chloride (\(C_6H_5N_2^+Cl^-\)) reacts with phenol in a cold, weakly alkaline medium (\(pH \approx 9-10\)).
The diazonium cation attacks the para position of the phenol ring.
The product is p-hydroxyazobenzene, which is an orange-coloured dye.
Reaction:
\[ C_6H_5-N \equiv N^+Cl^- + C_6H_5OH \xrightarrow{OH^-} C_6H_5-N=N-C_6H_4-OH + HCl \]
Step 4: Final Answer:
The reaction produces p-hydroxyazobenzene, an orange azo dye.
Was this answer helpful?
0