Toluene is nitrated and the resulting product is reduced with tin and hydrochloric acid. The product so obtained is diazotised and then heated with cuprous bromide. The reaction mixture so formed contains
- mixture of o-and-p-bromotoluenes
- mixture of o-and p-dibromobenzene
- mixture of o-and p-bromoaniline
- mixture of o-and m-bromotoluenes
The Correct Option is A
Solution and Explanation
Top Questions on Amines
Amines have a lone pair of electrons on the nitrogen atom, due to which they behave as Lewis bases. Greater the value of \( K_b \) or smaller the value of \( pK_b \), stronger is the base. Amines are more basic than alcohols, ethers, esters, etc. The basic character of aliphatic amines should increase with the increase of alkyl substitution. However, it does not occur in a regular manner, as a secondary aliphatic amine is unexpectedly more basic than a tertiary amine in aqueous solutions. Aromatic amines are weaker bases than ammonia and aliphatic amines. Electron-releasing groups such as \( -CH_3 \), \( -NH_2 \), etc., increase the basicity, while electron-withdrawing substituents such as \( -NO_2 \), \( -CN \), halogens, etc., decrease the basicity of amines. The effect of these substituents is more pronounced at the para-position than at the meta-position.
(a) Arrange the following in increasing order of their basic character. Give reason:
\[ \includegraphics[width=0.5\linewidth]{ch29i.png} \]- Amines have a lone pair of electrons on nitrogen atom due to which they behave as Lewis base. Greater the value of \( K_b \) or smaller the value of \( pK_b \), stronger is the base. Amines are more basic than alcohols, ethers, esters, etc. The basic character of aliphatic amines should increase with the increase of alkyl substitution. But it does not occur in a regular manner as a secondary aliphatic amine is unexpectedly more basic than a tertiary amine in aqueous solutions. Aromatic amines are weaker bases than ammonia and aliphatic amines. Electron releasing groups such as \(–CH_3\), \(–NH_2\), etc., increase the basicity while electron-withdrawing substituents such as \(–NO_2\), –CN, halogens, etc., decrease the basicity of amines. The effect of these substituents is more at the p₊ than at m₋ position.
- Assertion (A): Aromatic primary amines cannot be prepared by Gabriel Phthalimide synthesis. Reason (R): Aryl halides do not undergo nucleophilic substitution reaction with the anion formed by phthalimide.
- Give plausible explanation for each of the following:
Aromatic primary amines cannot be prepared by Gabriel Phthalimide synthesis. - Give plausible explanation for each of the following:
Amides are less basic than amines.
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Concepts Used:
Amines
Amine is a type of compound which is derived from ammonia (NH3). According to Organic chemistry, they are basically classified as the functional groups of the organic nitrogen compounds that contain nitrogen atoms with a lone pair.
Amine - Types
Primary Amines:
It is formed when one hydrogen atom in ammonia is substituted by an alkyl or aromatic group. Amino acids and methyl amine are the best examples that why aromatic amines include aniline.
Secondary Amines:
Amines that have two organic substitutes either alkyl or aryl ones or both and are bound to the nitrogen together with one hydrogen are termed as secondary amines. For Example, Dimethylamine.
Tertiary Amines:
Tertiary Amines are the amines where the nitrogen consists of three organic substitutes. For example, Trimethylamine and EDTA.