No, aniline cannot be prepared by Gabriel phthalimide reaction. This method involves the treatment of potassium phthalimide with aryl halides. But aryl halides does not undergo nucleophilic substitution under ordinary conditions.

Alkyl and aryl secondary amines react with nitrous acid to give N - nitroso amine as yellow oily liquid which is insoluble in water

This reaction is known as Libermann's nitroso test.

In simple amines the lone pair of electrons is on nitrogen and hence available for protonation. In amides, on the other hand, the electron pair on nitrogen is delocalized to the carbonyl oxygen through resonance.

Aniline decolourises bromine water with the formation of white precipitate which is 2,4,6-tribromo aniline

(i) Amines are compounds derived from ammonia by replacing one or more hydrogen atoms by alkyl or aryl group.
(ii) They are classified as primary, secondary and tertiary amines.
(a) When one of the hydrogen atoms in NH₃ is replaced by alkyl, it is primary amine CH₃NH methyl aminefl
(b) If two hydrogen atoms of amine group are replaced by alkyl groups, it is a secondary amine (CH₃)₂ NH- dimethylamine (2°).
(c) If three hydrogen atoms of amine group are replaced by alkyl groups, it is a tertiary amine. (CH₃)₃ N-trimethylamine (3°). Aromatic amine - C₆H₅NH₂ Aline

Nitrobenzene does not undergo Friedel - Crafts reactions due to the strong deactivating nature of -NO₂ group.

a) Primary and secondary nitroalkanes, having α-H, also show an equilibrium mixture of two tautomers namely nitro - and aci - form

b) Difference:

Hoffmann's bromide reaction:
When Amides are treated with bromine in the presence of aqueous or ethanolic solution of KOH, primary amines with one carbon atom less than the parent amides are obtained.
\(\underset { \quad \quad \quad amide\\ R=Alkyl(or)Aryl }{ R-\overset { \underset { || }{ O } }{ C } -{ NH }_{ 2 } } \overset { { Br }_{ 2 }/KOH }{ \longrightarrow } \underset { Primary\quad amine }{ R-{ NH }_{ 2 }+{ K }_{ 2 }{ CO }_{ 3 } } +KBr+{ H }_{ 2 }O\)
(ii) Hoffmann's ammonolysis:
When Alkyl halides (or) benzylhalides are heated with alcoholic ammonia in a sealed tube, mixtures of 1°, 2° and 3° amines and quaternary ammonium salts are obtained.
\( { CH }_{ 3 }-Br\overset { \ddot { N } { H }_{ 3 } }{ \underset { \Delta }{ \longrightarrow } } \underset { { 1 }^{ 0 }-amine }{ { CH }_{ 3 }-\ddot { N } { H }_{ 2 } } \overset { { CH }_{ 3 }-Br }{ \longrightarrow } \underset { { 3 }^{ o }-amine }{ \left( { CH }_{ 3 } \right) _{ 2 }\ddot { N } H } \overset { { CH }_{ 3 }Br }{ \longrightarrow } \underset { 3^{ o }-amine }{ \left( { { CH }_{ 3 } } \right) _{ 3 }\ddot { N } } \overset { CH_{ 3 }Br }{ \longrightarrow } \underset { Quartenary \ ammonium\ bromide }{ \left( { CH }_{ 3 } \right) _{ 4 }\overset { + }{ N } { Br }^{ - } } \) 
This is a nucleophilic substitution, the halide ion of alkyl halide is substituted by the -NH₂ group. The product primary amine so formed can also has a tendency to act as a nucleophile and hence if excess alkyl halide is taken, further nucleophilic substitution takes place leading to the formation of quarternary ammonium salt. However, if the process is carried out with excess ammonia, primary amine is obtained as the major product. The order of reactivity of alkylhalides with amines
RI > RBr > RCl
(iii) Gabriel phthalimide synthesis:
Gabriel synthesis is used for the preparation of Aliphatic primary amines. Phthalimide on treatment with ethanolic KOH forms potassium salt of phthalimide which on heating with alkyl halide followed by alkaline hydrolysis gives primary amine. Aniline cannot be prepared by this method because the arylhalides do not undergo nucleophilic substitution with the anion formed by phthalimide.

(iv) Schotten - Baumann reaction :
Aniline reacts with benzoylchloride (C₆H₅COCI) in the presence of NaOH to give N - phenyl benzamide. This reaction is known as Schotten - Baumann reaction. The acylation and benzoylation are nucleophilic substitutions.
\(\underset { Aniline }{ { C }_{ 6 }{ H }_{ 5 }-{ NH }_{ 2 } } +\underset { Benzoyl\quad chloride }{ { C }_{ 6 }{ H }_{ 5 }-\overset { \underset { || }{ O } }{ C } -Cl } \overset { Pyridine }{ \longrightarrow } \underset { N-phenyl\quad benzamide }{ { C }_{ 6 }{ H }_{ 5 }-NH-\overset { \underset { || }{ O } }{ C } -{ C }_{ 6 }{ H }_{ 5 } } +HCl\)
(v) Carbylamine reaction :
Aliphatic (or) aromatic primary amines react with: chloroform and alcoholic KOH to give isocyanides (carbylamines), which has an unpleasant smell. This reaction is known as carbylamines test. This test used to identify the primary amines.
\(\underset { Ethylamine }{ { C }_{ 2 }{ H }_{ 5 }-{ NH }_{ 2 } } +\underset { Chloroform }{ { CHCl }_{ 3 }+3KOH } \longrightarrow \underset { Ethylisocyanide }{ { C }_{ 2 }{ H }_{ 5 }-NC } +3KCl+3{ H }_{ 2 }O\)
(vi) Mustard oil reaction:
(a) When primary amines are treated with carbon disulphide (CS₂), N - alkyldithio carbonic acid is formed which on subsequent treatment with HgCI₂, gives an alkyl isothiocyanate.


(b) When aniline is treated with carbon disulphide, or heated together, S-diphenylthio urea is formed, which on boiling with strong HCI, phenyl isothiocyanate (phenyl mustard oil), is formed.

These reactions are known as Hofmann - Mustard oil reaction. This test is used to identify the primary amines.
(vii) Coupling reactions (or) p-hydroxyazobenzene, p-aminoazobenzene, 2-phenyl azo-4-methyl phenol:
Benzene diazonium chloride reacts with electron rich aromatic compounds like phenol, aniline to form brightly coloured azo compounds. Coupling generally occurs at the para position. If para position is occupied then coupling occurs at the ortho position. Coupling tendency is enhanced if an electron donating group is present at the para - position to -N₂CI- group. This is an electrophilic substitution.

Aryl fluorides and iodides cannot be prepared by direct halogenation and the cyano group cannot be introduced by nucleophilic substitution of chlorine in chlorobenzene. For introducing such a halide group. cyano group -OH, NO₂, etc.. benzenediazonium chloride is a very good intermediate Diazo compounds obtained from the coupling reactions of diazonium salts are coloured and are used as dyes.
(viii) Diazotisation :
Aniline reacts with nitrous acid at low temperature (273 - 278 K) to give benzene. Diazonium chloride which is stable for a short time and slowly decomposes even at low temperatures.This reaction is known as diazotization

(ix) Gomberg reaction :
Benzene diazonium chloride reacts with benzene in the presence of sodium hydroxide to give biphenyl. This reaction in known as the Gomberg reaction

 +CO₂

Nitrobenzene into 1,3,5 - trinitro benzene

Nitrobenzene                                 1,3,5 - trinitro benzene
ii. Nitrobenzene into o - and p - nitro phenols

iii. Nitrobenzene into m - nitro aniline
  + 6NH₃ + 2H₂O + 3S
iv. Nitrobenzene into azoxybenzene
+3H₂O
v. Nitrobenzene into hydrazobenzene

vi. Nitrobenzene into N - phenyl hydrazobenzene

vii. Nitrobenzene into aniline

i) 2 - nitro propane is boiled with HCI:

It gives acetone.
ii) Nitrobenzene on electrolytic reduction in strongly acidic medium:

It gives aniline, phenyl hydroxylamine and p - amino phenol
iii) Oxidation of text – butylamine with KMnO₄:

It gives 2 - methyl - 2- nitro propane is obtained.
iv) Oxidation of acetoneoxime with trifluoroperoxy acetic acid.

It gives 2 - nitro propane.