Question:medium

Which of the following statements is/are true about phenoxide ions?

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Solvent polarity and hydrogen-bonding ability strongly influence whether phenoxide ions undergo O-alkylation or C-alkylation.
Updated On: Jun 5, 2026
  • Phenoxides undergo O-alkylation in ethers
  • Phenoxides undergo extensive C-alkylation in trifluoroethanol
  • Ethers make strong hydrogen bonds with the oxygen atom of phenoxide ions to improve solvation
  • C-alkylation disrupts aromatic conjugation of phenoxide ions
Show Solution

The Correct Option is A, B

Solution and Explanation

Step 1: Set up the phenoxide.
Removing a proton from phenol gives the phenoxide ion, whose negative charge is shared between the oxygen and the ring.

Step 2: Behaviour in ether.
In a weakly interacting ether solvent the oxygen stays very nucleophilic, so alkylation lands on oxygen. That is O-alkylation, making statement A true.

Step 3: Behaviour in trifluoroethanol.
This solvent donates strong hydrogen bonds and ties up the oxygen, lowering its reactivity. Now the ring carbon takes over, so C-alkylation rises and statement B is true.

Step 4: Reject C and D.
Ethers have no acidic hydrogen, so they cannot hydrogen bond strongly to the phenoxide oxygen, making C false. C-alkylation happens at ortho or para while keeping the ring aromatic, so D is false too.

Step 5: Answer.
\[ \boxed{A,\ B} \]
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