How would you carry out the following conversion? Benzyl chloride to benzyl alcohol

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Detailed Solution

Conversion: Benzyl Chloride (C₆H₅CH₂Cl) → Benzyl Alcohol (C₆H₅CH₂OH)

Convert benzyl chloride to benzyl alcohol via nucleophilic substitution (SN1/SN2 depending on conditions), replacing Cl with OH⁻.

Reaction

C₆H5CH₂Cl + NaOH → C₆H₅CH₂OH + NaCl

Method

Reagents: Aqueous NaOH (or KOH).
Conditions: Heat under reflux. The hydroxide ion attacks the benzylic carbon, displacing Cl⁻.
Workup: Isolate benzyl alcohol after completion (e.g., extraction, drying, and purification as needed).

Alternative Methods

Hydrolysis with water in the presence of base.
Moist silver oxide (Ag₂O + H₂O) to generate OH⁻ in situ and facilitate halide displacement.

Key Point: This is a straightforward benzylic halide → alcohol conversion by nucleophilic substitution where –Cl is replaced by –OH.

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