13.11. Complete the following reactions:

(i) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{2}+\mathrm{CHCl}_{3}+ alc. \mathrm{KOH} \rightarrow\)

(ii) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{~N}_{2} \mathrm{Cl}+\mathrm{H}_{3} \mathrm{PO}_{2}+\mathrm{H}_{2} \mathrm{O} \rightarrow\)

(iii) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{2}+\mathrm{H}_{2} \mathrm{SO}_{4} (conc.) \rightarrow\)

(iv) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{~N}_{2} \mathrm{Cl}+\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{OH} \rightarrow\)

(v) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{2}+\mathrm{Br}_{2}(\mathrm{aq}) \rightarrow\)

(vii) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{2}+\left(\mathrm{CH}_{3} \mathrm{CO}\right)_{2} \mathrm{O} \rightarrow\)
(viii)  \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{~N}_{2} \mathrm{Cl} \)
 \(\xrightarrow[2. NaNO_{2}/Cu]{1. HBF_{4}}\)

 

(i)
The given reaction is an example of a carbylamine test.  

C6H5NH2+CHCl3+3alc. KOHCarbylamine
reaction3H2O+3KCl+C6H5-NC
Aniline                                                                                             Phenyl isocyanide

(ii)
In this reaction, benzenediazonium salt is converted into benzene as a product.

C6H5N2Cl+H3PO2+H2OC6H6+N2+H3PO3+HCl
Benzenediazonium                Benzene
chloride

(iii)
In this reaction, aniline gives acid-base reaction with conc. sulphuric acid and  form anilinium ion as a product.

C6H5NH2+conc.H2SO4C6H5N+H3HSO-4
Aniline                                 Anilinium hydrogen sulphate

(iv)

In this reaction, benzene diazonium salt reacts with ethanol and forms benzene as the main product.

C6H5N2Cl + C2H5OH  C6H6 + CH3CHO + N2 + HCl
Benzenediazonium Ethanol Benzene    Ethanal
chloride

(v)
The given reaction is an example of an electrophilic aromatic substitution reaction. The NH2 group activates the benzene ring and a bromination reaction occurs at the ortho and para positions. 

(vi)
In this reaction, aniline undergoes an acetylation reaction when reacts with acetic anhydride as follows: 

(vii)
In the reaction, benzene diazonium chloride first reacts with HBF4 , and diazonium fluoroborate is obtained as a product. 
In the next step, diazonium fluoroborate is heated with an aqueous sodium nitrite solution in the presence of copper, the diazonium group is replaced by the –NO2 group.

   C6H5N2CL(ii) NaNO2/Cu,(i)HBF4C6H5NO2+N2+NaBF4
Benzenediazonium                Nitrobenzene
chloride