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In the reaction sequence: A --[SnCl2/HCl]--> B --[NaNO2/HCl, 0 deg C]--> C --[H2O/heat]--> C6H5OH. Identify compounds A, B, and C.

1. A = Nitrobenzene, B = Aniline, C = Benzenediazonium chloride
2. A = Benzene, B = Nitrobenzene, C = Aniline
3. A = Benzene diazonium chloride, B = Aniline, C = Nitrobenzene
4. A = Aniline, B = Nitrobenzene, C = Benzenediazonium chloride

Correct answer: A = Nitrobenzene, B = Aniline, C = Benzenediazonium chloride

Solution

Tracing the reaction backward: C6H5OH (phenol) is obtained by warming benzenediazonium chloride (C) with water (Sandmeyer/hydrolysis). Benzenediazonium chloride (C) is formed by treating aniline (B) with NaNO2/HCl at 0 deg C (diazotization). Aniline (B) is obtained by reducing nitrobenzene (A) with SnCl2/HCl (reduction of -NO2 to -NH2). Therefore A = Nitrobenzene, B = Aniline, C = Benzenediazonium chloride.

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