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Question : 34
Total: 35
(a) (I) Give reasons:
(i) Aniline on nitration gives good amount of m-nitroaniline, though -N H 2 group is o ∕ p directing in electrophilic substitution reactions.
(ii)( C H 3 ) 2 N H is more basic than ( C H 3 ) 3 N in an aqueous solution.
(iii) Ammonolysis of alkyl halides is not a good method to prepare pure primary amines.
(II) Write the reaction involved in the following:
(i) Carbyl amine test
(ii) Gabriel phthalimide synthesis
OR
(b) (I) Write the structures of A, B and C in the following reactions:
(III)Arrange the following in increasing order of their boiling point:C 2 H 5 O H , C 2 H 5 N H 2 , ( C 2 H 5 ) 3 N
(i) Aniline on nitration gives good amount of m-nitroaniline, though -
(ii)
(iii) Ammonolysis of alkyl halides is not a good method to prepare pure primary amines.
(II) Write the reaction involved in the following:
(i) Carbyl amine test
(ii) Gabriel phthalimide synthesis
OR
(b) (I) Write the structures of A, B and C in the following reactions:
(II) Why aniline does not undergo Friedal-Crafts reaction?
(III)Arrange the following in increasing order of their boiling point:
Solution: 👈: Video Solution
(a) (I) (i) Nitration is carried out in an acidic medium. In a strongly acidic medium, aniline is protonated to give anilinium ion which is metadirecting. Therefore, aniline on nitration gives a substantial amount of m-nitroaniline.
(ii)( C H 3 ) 2 N H is more basic than ( C H 3 ) 3 N in an aquous solution. As the number of methyl groups increases, the extent of hydration decreases due to steric hindrance. Greater is the extent of hydration, greater is the stability of ion and greater is the basic strength of amine.
(iii) Ammonolysis of alkyl halides leads to the formation of a mixture of primary, secondary, tertiary amines and quaternary salts which is very difficult to separate and obtain pure amine.
(II) (i) Carbyl Amine Test
+ 3 K O H →
(b) (I) (i)C 6 H 5 N 2 C l
( C 6 H 5 C O O N H 4 )
A l C l 3 being electron deficient acts as a Lewis base and attacks on the lone pair of nitrogen present in aniline to form insoluble complex which precipitates out and does not proceed.
(III) Increasing order of boiling points:
( C H 3 ) 3 N < C 2 H 5 N H 2 < C 2 H 5 O H
(ii)
(iii) Ammonolysis of alkyl halides leads to the formation of a mixture of primary, secondary, tertiary amines and quaternary salts which is very difficult to separate and obtain pure amine.
(II) (i) Carbyl Amine Test
OR
(b) (I) (i)
(II) It is due to the fact that
(III) Increasing order of boiling points:
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