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Fundamentals of Organic ChemistryChemistryAlcohols Phenols and Ethers

Identify the major product formed in the following reaction sequence: [ (ii) Mg , Et ₂ O ] (i) Cl ₂, AlCl ₃ [ (iv) PCC ] (iii) HCHO , then H ₂ O Product

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Step-by-step solution

Benzene reacts with Cl ₂ in the presence of AlCl ₃ to undergo electrophilic aromatic substitution, forming chlorobenzene. Chlorobenzene reacts with Mg in dry ether to form the Grignard reagent, phenylmagnesium chloride ( C ₆ H ₅ MgCl ). Phenylmagnesium chloride undergoes nucleophilic addition with formaldehyde ( HCHO ) followed by hydrolysis to yield benzyl alcohol ( C ₆ H ₅ CH ₂ OH ). Benzyl alcohol, a primary alcohol, is oxidized by Pyridinium chlorochromate (PCC) to form benzaldehyde ( C ₆ H ₅ CHO ). Answer:

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