(a) Give one chemical test to distinguish between the compounds of the following pairs :

     (i) CH_{3}NH_{2} and (CH_{3})_{2}NH

    (ii) Aniline and Ethanamine

(b) Why aniline does not undergo Friedel-Crafts reaction ?

 

 

 

 
 
 
 
 

Answers (1)
S Sumit

(a) (1) CH_{3}NH_{2} and (CH_{3})_{2}NH

CH_{3}NH_{2} being a primary amine on reaction with chloroform in presence of alcoholic alkali gives bad smelling alkyl isocyanide.

CH_{3}NH_{2}+CHCl_{3}+\underset{(alc)}{3KOH}\rightarrow CH_{3}N\rightarrow C+3KCl+3H_{2}O

(2) Aniline and ethanamine 

       Aniline on coupling with benzene diazonium chloride gives a yellow dye but ethanamine does not 

(b) Aniline does not undergo priedel crafts reaction due to salt, formation between aniline and the catalyst anhydrous AlCl_{3} (lewis acid) as a result N acquires positive charge and acts as a deactivating group for further reaction.

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