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13.11. Complete the following reactions:

(i) C6H5NH2+CHCl3+alc.KOH

(ii) C6H5 N2Cl+H3PO2+H2O

(iii) C6H5NH2+H2SO4(conc.)

(iv) C6H5 N2Cl+C2H5OH

(v) C6H5NH2+Br2(aq)

(vii) C6H5NH2+(CH3CO)2O
(viii)  C6H5 N2Cl
 1.HBF42.NaNO2/Cu

 

(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.H2SO4C6H5+NH3HS-O4
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(i)HBF4(ii) NaNO2/Cu,C6H5NO2+N2+NaBF4
Benzenediazonium                Nitrobenzene
chloride