How will you distinguish between primary secondary and tertiary alphatic amines.

Account for the following
i. Aniline does not undergo Friedel – Crafts reaction
ii. Diazonium salts of aromatic amines are more stable than those of aliphatic amines
iii. pK_b of aniline is more than that of methylamine
iv. Gabriel phthalimide synthesis is preferred for synthesising primary amines.
v. Ethylamine is soluble in water whereas aniline is not
vi. Amines are more basic than amides
vii.Although amino group is o – and p – directing in aromatic electrophilic substitution reactions, aniline on nitration gives a substantial amount of m – nitroaniline.

Arrange the following
i. In increasing order of solubility in water, C₆H₅ NH₂, (C₂H₅)₂NH, C₂H₅NH₂
ii. In increasing order of basic strength
a) aniline, p- toludine and p – nitroaniline
b) C₆H₅ NH₂, C₆H₅ NHCH₃, C₆H₅NH₂, p-Cl-C₆- H₄-NH₂
iii. In decreasing order of basic strength in gas phase
(C₂H₅)NH₂, (C₂H₅)NH, (C₂H₅)₅N and NH₃
iv. In increasing order of boiling point
C₆H₅OH, (CH₃)₂NH, C₂H₅NH₂
v. In decreasing order of the pK_b values
C₂H₅NH₂, C₆H₅NHCH₃.(C₂H₅)₂ NH and CH₃NH₂
vi. Increasing order of basic strength
C₂H₅NH₂,C₆H₅N(CH₃)₂, (C₂H₅)₂ NH and CH₃NH₂
vii. In decreasing order of basic strength

How will you prepare propan – 1- amine from
i) butane nitrile
ii) propanamide
ii) 1- nitropropane

Identify A,B,and C
CH₃- NO₂ \(\overset { { L }_{ 1 }{AlH }_{ 4 } }{ \underset { {} }{ \longrightarrow } }\) A  \(\overset { { 2CH_3 }{Ch_2Br } }{ \underset { {} }{ \longrightarrow } }\) B \(\overset { {H}_{ 2 }{SO}_{ 4 } }{ \underset { {} }{ \longrightarrow } } \) C