See image — Alcohols Phenols and Ethers Chemistry Question

💡 Solution & Explanation

Step 1: Identify the starting material. The compound is 1,2,3,4-tetrahydronaphthalen-1-ol (1-tetralol), which has a hydroxyl group at the benzylic C1 position of the tetralin ring system. Step 2: First reaction — TsCl / Pyridine. Tosyl chloride in pyridine converts the alcohol (-OH) into a tosylate (-OTs), a good leaving group, without breaking any C-O bond of the original molecule. The configuration at C1 is retained (the reaction occurs at sulfur, not carbon). Product (A) is 1-tosyloxy-1,2,3,4-tetrahydronaphthalene (the tosylate ester). Step 3: Second reaction — LiAlH4. Lithium aluminum hydride is a strong hydride reducing agent. It reduces tosylates via an SN2 mechanism: hydride (H-) acts as the nucleophile, displacing the tosylate leaving group with inversion of configuration at C1. The net result is replacement of OTs with H, effectively deoxygenating the alcohol. Product (B) is 1,2,3,4-tetrahydronaphthalene (tetralin) — the fully saturated ring fused to benzene, with no substituent at C1. Step 4: Why this is the correct answer (C). The two-step sequence (tosylation then LiAlH4 reduction) is a classic method for removing a hydroxyl group (deoxygenation via tosylate). The product is simply tetralin (1,2,3,4-tetrahydronaphthalene), which corresponds to option C in the original question set. Therefore, the correct answer is C.