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Write Brief Answer · Q5

Q.Identify compounds A, B and C in the following sequences of reactions:

i) C6H5NO2 --Fe/HCl--> A --HNO2, 273 K--> B --C6H5OH--> C
ii) C6H5N2+Cl- --CuCN--> A --H2O/H+--> B --NH3--> C
iii) CH3CH2I --NaCN--> A --H3O+, partial hydrolysis--> B --NaOH + Br2--> C
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Step 1. i) C6H5NO2 + Fe/HCl reduces to A = aniline. A + HNO2 at 273 K diazotises to B = benzenediazonium chloride. B + C6H5OH (phenol, an electron-rich coupling partner) is the coupling reaction (retention of the diazo group), giving C = p-hydroxyazobenzene, an orange azo dye, coupling occurring at phenol's para position.

Step 2. ii) C6H5N2+Cl- + CuCN is the Sandmeyer reaction, replacing -N2+ with -CN to give A = cyanobenzene (benzonitrile). A + H2O/H+ is complete acid hydrolysis of the nitrile, giving B = benzoic acid. B + NH3 forms the ammonium salt directly, giving C = ammonium benzoate (the same intermediate the unit's own P2O5-dehydration route to benzonitrile would start from, closing a loop back toward the nitrile if driven further). …

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