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Q6.11(iv):
How will you bring about the following conversions? (iv) Toluene to benzyl alcohol

Solution :

Given Variables & Initial Setup

The objective is to convert Toluene ($C_6H_5CH_3$) to Benzyl alcohol ($C_6H_5CH_2OH$). This transformation involves the functionalization of the side-chain methyl group of an aromatic hydrocarbon.

Step 1: Radical Halogenation of Toluene

Toluene is subjected to free-radical chlorination using chlorine gas in the presence of ultraviolet light or heat. This ensures substitution occurs at the benzylic position rather than the aromatic ring.

$C_6H_5CH_3 + Cl_2 \xrightarrow{h\nu / \Delta} C_6H_5CH_2Cl + HCl$

[Justification: Per the mechanism of free-radical substitution, the benzylic radical is stabilized by resonance with the aromatic ring, making the benzylic hydrogen highly reactive toward radical abstraction.]

Step 2: Nucleophilic Substitution (Hydrolysis)

The resulting Benzyl chloride ($C_6H_5CH_2Cl$) is treated with an aqueous alkali (such as aqueous $KOH$ or $NaOH$).

$C_6H_5CH_2Cl + KOH_{(aq)} \xrightarrow{\Delta} C_6H_5CH_2OH + KCl$

[Justification: This proceeds via an $S_N2$ mechanism. The hydroxide ion ($OH^-$) acts as a strong nucleophile, displacing the chloride ion ($Cl^-$) from the primary carbon atom.]

Visual Representation of the Reaction Pathway

Toluene CH₃ Cl₂, hv CH₂Cl aq. KOH CH₂OH

Reaction Summary Table

Step Reagents Mechanism Product
1 $Cl_2, h\nu$ Free Radical Substitution Benzyl Chloride
2 $aq. KOH$ $S_N2$ Nucleophilic Substitution Benzyl Alcohol

Final Solution: The conversion of Toluene to Benzyl alcohol is achieved in two steps: first, free-radical chlorination to form Benzyl chloride ($C_6H_5CH_2Cl$), followed by aqueous alkaline hydrolysis to yield Benzyl alcohol ($C_6H_5CH_2OH$).


More Questions from Class 12 Chemistry Haloalkanes and Haloarenes Exercises


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