Match Organic Reactions with Corresponding Reaction Mechanisms

To determine the correct matching between List-I (Organic Reactions) and List-II (Reaction Mechanisms), let us analyze each reaction individually:

1. A. Williamson Synthesis:

   • Reaction: An alkyl halide reacts with an alkoxide ion to form an ether: $R-\text{X} + R'-\text{O}^- \text{Na}^+ \longrightarrow R-\text{O}-R' + \text{NaX}$
   • Mechanism: The alkoxide ion acts as a strong nucleophile and attacks the primary alkyl halide via a bimolecular nucleophilic substitution ($\text{S}_\text{N}2$) pathway.
   • Match: A $\rightarrow$ III (Nucleophilic substitution)

2. B. Friedel-Crafts Reaction:

   • Reaction: Benzene reacts with an alkyl halide or acyl halide in the presence of a Lewis acid catalyst (e.g., $\text{AlCl}_3$) to yield an alkylbenzene or acylbenzene.
   • Mechanism: The Lewis acid generates a carbocation or acylium ion (electrophile), which attacks the electron-rich aromatic ring, leading to an aromatic electrophilic substitution ($\text{S}_\text{E}\text{Ar}$).
   • Match: B $\rightarrow$ IV (Electrophilic substitution)

3. C. Bromination of vinyl benzene:

   • Reaction: Vinyl benzene (styrene, $\text{C}_6\text{H}_5-\text{CH}=\text{CH}_2$) reacts with bromine ($\text{Br}_2$).
   • Mechanism: The $\pi$-electrons of the carbon-carbon double bond ($\text{C}=\text{C}$) attack the electrophilic bromine molecule to form a bromonium ion intermediate, followed by nucleophilic attack of $\text{Br}^-$. This is a characteristic electrophilic addition reaction across an alkene double bond.
   • Match: C $\rightarrow$ I (Electrophilic addition)

4. D. Chlorination of toluene in light:

   • Reaction: Toluene reacts with chlorine gas in the presence of sunlight ($h\nu$): $\text{C}_6\text{H}_5-\text{CH}_3 + \text{Cl}_2 \xrightarrow{h\nu} \text{C}_6\text{H}_5-\text{CH}_2\text{Cl} + \text{HCl}$
   • Mechanism: Sunlight initiates the homolytic cleavage of $\text{Cl}_2$ to generate chlorine free radicals, leading to a halogenation of the side-chain methyl group via a free radical substitution mechanism.
   • Match: D $\rightarrow$ II (Free radical substitution)

---

Correct Match:

• A $\rightarrow$ III
• B $\rightarrow$ IV
• C $\rightarrow$ I
• D $\rightarrow$ II

This corresponds to Option C.