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Formation of Salicylic acid from phenol ...

Formation of Salicylic acid from phenol (Kolbe's reaction) is an example of

A

Electrophilic addition reaction

B

Nucleophilic addition reaction

C

Electrophilic substitution reaction

D

Nucleophilic substitution reaction

Text Solution

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The correct Answer is:
To determine the type of reaction that describes the formation of salicylic acid from phenol via Kolbe's reaction, we can analyze the process step by step. ### Step-by-Step Solution: 1. **Identify the Reactants**: The reaction begins with phenol (C6H5OH) and sodium hydroxide (NaOH). 2. **Formation of Phenoxide Ion**: When phenol reacts with NaOH, it forms the phenoxide ion (C6H5O⁻). This occurs because the hydroxide ion (OH⁻) from NaOH deprotonates the hydroxyl group of phenol, resulting in the formation of a negatively charged ion. - **Hint**: Look for how bases can deprotonate acids to form their conjugate bases. 3. **Electrophilic Attack**: The phenoxide ion, which is resonance-stabilized, can act as a nucleophile. It attacks carbon dioxide (CO2), which acts as an electrophile. This step is crucial as it leads to the formation of a carboxylate ion. - **Hint**: Identify the roles of nucleophiles and electrophiles in a reaction. 4. **Formation of Salicylic Acid**: The product of the reaction between the phenoxide ion and CO2 is a carboxylate ion (C6H4(OH)(COO⁻)). When this carboxylate ion is treated with an acid (like H2SO4 or H3O⁺), it leads to the protonation of the carboxylate ion, forming salicylic acid (C6H4(OH)(COOH)). - **Hint**: Consider how acids can protonate negative charges to form neutral compounds. 5. **Conclusion**: The overall process is an electrophilic substitution reaction, where the phenoxide ion undergoes substitution with CO2 to form salicylic acid. ### Final Answer: The formation of salicylic acid from phenol via Kolbe's reaction is an example of **electrophilic substitution reaction**.
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