See image — Alcohols Phenols and Ethers Chemistry Question

💡 Solution & Explanation

Concept: When an aryl alkyl ether is treated with HI, cleavage occurs preferentially at the alkyl-oxygen bond (not the aryl-oxygen bond) because the C(aryl)-O bond is strengthened by resonance with the aromatic ring and is much harder to cleave. This produces an alkyl iodide and a phenol. Step 1: Reaction of 1-Phenoxypropane (C6H5-O-CH2CH2CH3) with excess conc. HI at 0°C. The HI cleaves the weaker alkyl C-O bond (not the aryl C-O bond). The iodide ion acts as a nucleophile attacking the alkyl carbon (SN2), giving: - n-propyl iodide (CH3CH2CH2I) - Phenol (C6H5OH) Step 2: The mixture of products (phenol + n-propyl iodide) is then treated with thionyl chloride (SOCl2). Thionyl chloride reacts with alcohols/phenols to replace the -OH group with -Cl. However, phenol reacts with SOCl2 less readily under normal conditions compared to aliphatic alcohols, and typically phenol does not give chlorobenzene easily under mild conditions with SOCl2 (it would require harsh conditions). n-Propyl iodide does not react with SOCl2 in the same way; SOCl2 replaces -OH with -Cl, not -I with -Cl under these conditions. Wait - re-examining: The products from HI cleavage are phenol and n-propyl iodide. When SOCl2 is added to this mixture, SOCl2 reacts with phenol (an alcohol equivalent, -OH group) to give chlorobenzene... but actually phenol + SOCl2 can give chlorobenzene under forcing conditions. However, the given correct answer is B: Phenol + n-propyl iodide, meaning the thionyl chloride step does NOT change these products, OR the question implies only the HI step matters for the final answer identification. Re-reading: The answer B is "Phenol + n-propyl iodide". This means thionyl chloride does not significantly alter these products under the described conditions, or the question is testing only the ether cleavage step. Aryl ethers cleave at the alkyl-O bond with HI to give phenol and alkyl iodide. n-Propyl iodide does not react with SOCl2 (SOCl2 reacts with -OH, not C-I bonds). Phenol can react with SOCl2 but under these mild/mixed conditions the predominant identified products remain phenol and n-propyl iodide. Why other options fail: - (a) n-propanol + Chlorobenzene: HI would not give an alcohol; it gives alkyl iodide. Chlorobenzene from SOCl2 on phenol is not the primary outcome here. - (c) n-propyl chloride + Chlorobenzene: Neither product is directly obtained; HI gives iodide not chloride, and chlorobenzene formation from phenol+SOCl2 is not straightforward. - (d) n-propyl chloride + Phenol: HI gives n-propyl iodide, not chloride; SOCl2 does not convert C-I to C-Cl. The key reaction is: aryl alkyl ether + HI → phenol + n-alkyl iodide (cleavage at alkyl C-O bond). SOCl2 does not convert the iodide to chloride under normal conditions. Therefore, the correct answer is B.