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  • Nitration of Toluene vs. Phenol: A Detailed Comparison
    Phenol is nitrated faster than toluene.

    Explanation:

    * Activation of the Aromatic Ring: The hydroxyl group (-OH) in phenol is a strongly activating group, meaning it increases the electron density of the aromatic ring. This makes the ring more susceptible to electrophilic attack, such as nitration.

    * Resonance Stabilization: The lone pair of electrons on the oxygen atom in phenol can delocalize into the aromatic ring, creating resonance structures. These resonance structures stabilize the intermediate carbocation formed during nitration, making the reaction more favorable.

    Mechanism of Nitration:

    Nitration involves the electrophilic attack of a nitronium ion (NO2+) on the aromatic ring. The activating nature of the hydroxyl group in phenol makes the ring more electron-rich, attracting the electrophile more readily.

    Comparison with Toluene:

    Toluene has a methyl group (-CH3), which is a weakly activating group. While the methyl group does increase the electron density of the ring, its effect is much less pronounced than that of the hydroxyl group in phenol.

    Conclusion:

    Due to the strong activating effect of the hydroxyl group and resonance stabilization, phenol is nitrated much faster than toluene.

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