Amines

An aromatic compound ‘A’ on treatment with aqueous ammonia and heating forms compound ‘B’ which on heating with Bromine and KOH forms a compound ‘C’ of molecular formula C6H7N. Write the structures and IUPAC names of compounds A, B, and C.

Compound ‘C,' with the molecular formula C6H7N, is created by heating compound ‘B' with Br2 and KOH, according to the formula. This is a decomposition of Hoffmann bromamide. As a result, compound B...

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Arrange the following:
(i) In decreasing order of basic strength in the gas phase:\[{{\mathbf{C}}_{\mathbf{2}}}{{\mathbf{H}}_{\mathbf{5}}}\mathbf{N}{{\mathbf{H}}_{\mathbf{2}}},\text{ }{{\left( {{\mathbf{C}}_{\mathbf{2}}}{{\mathbf{H}}_{\mathbf{5}}} \right)}_{\mathbf{2}}}\mathbf{NH},\text{ }{{\left( {{\mathbf{C}}_{\mathbf{2}}}{{\mathbf{H}}_{\mathbf{5}}} \right)}_{\mathbf{3}}}\mathbf{N}\text{ }\mathbf{and}\text{ }\mathbf{N}{{\mathbf{H}}_{\mathbf{3}}}\] (ii) In increasing order of boiling point:\[{{\mathbf{C}}_{\mathbf{2}}}{{\mathbf{H}}_{\mathbf{5}}}\mathbf{OH},\text{ }{{\left( \mathbf{C}{{\mathbf{H}}_{\mathbf{3}}} \right)}_{\mathbf{2}}}\mathbf{NH},\text{ }{{\mathbf{C}}_{\mathbf{2}}}{{\mathbf{H}}_{\mathbf{5}}}\mathbf{N}{{\mathbf{H}}_{\mathbf{2}}}\] (iii) In increasing order of solubility in water:\[{{\mathbf{C}}_{\mathbf{6}}}{{\mathbf{H}}_{\mathbf{5}}}\mathbf{N}{{\mathbf{H}}_{\mathbf{2}}},\text{ }{{\left( {{\mathbf{C}}_{\mathbf{2}}}{{\mathbf{H}}_{\mathbf{5}}} \right)}_{\mathbf{2}}}\mathbf{NH},\text{ }{{\mathbf{C}}_{\mathbf{2}}}{{\mathbf{H}}_{\mathbf{5}}}\mathbf{N}{{\mathbf{H}}_{\mathbf{2}}}\]

(i) There is no solvation effect in the gas phase. As a result, the + I impact is primarily responsible for the fundamental strength. The firmer the base, the larger the +I impact. In addition, the...

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Arrange the following in increasing order of basic strength:
(a) Aniline, p-nitroaniline and p-toluidine
\[\left( \mathbf{b} \right)\text{ }{{\mathbf{C}}_{\mathbf{6}}}{{\mathbf{H}}_{\mathbf{5}}}\mathbf{N}{{\mathbf{H}}_{\mathbf{2}}},\text{ }{{\mathbf{C}}_{\mathbf{6}}}{{\mathbf{H}}_{\mathbf{5}}}\mathbf{NHC}{{\mathbf{H}}_{\mathbf{3}}},\text{ }{{\mathbf{C}}_{\mathbf{6}}}{{\mathbf{H}}_{\mathbf{5}}}\mathbf{C}{{\mathbf{H}}_{\mathbf{2}}}\mathbf{N}{{\mathbf{H}}_{\mathbf{2}}}.\]

(a) The presence of the electron-donating – CH3 group in p – toluidine boosts the electron density on the N-atom. As a result, p – toluidine has higher basicity than aniline. In the case of p...

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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) Gabriel phthalimide synthesis is preferred for synthesizing primary amines

(i) Aniline does not undergo Friedel – Crafts reaction. In the presence of AlCl 3, the Friedel–Crafts reaction is carried out. However, we already know that AlCl 3 is acidic, whereas aniline is not....

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Account for the following:
(i) Methylamine in water reacts with ferric chloride to precipitate hydrated ferric oxide.
(ii) Although the amino group is o– and p– directing in aromatic electrophilic substitution reactions, aniline on nitration gives a substantial amount of m-nitroaniline.

(i) Methylamine in the water when made to react with ferric chloride, precipitates hydrated ferric oxide. Water is less basic than methylamine due to the presence of the – CH3 group and the + I...

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