Account for the following:
(i) pKb of aniline is more than that of methylamine.
(ii) Ethylamine is soluble in water whereas aniline is not.
(iii) Methylamine in water reacts with ferric chloride to precipitate hydrated ferric oxide.
(iv) Although amino group is o– and p– directing in aromatic electrophilic substitution reactions, aniline on nitration gives a substantial amount of m-nitroaniline.
(v) Aniline does not undergo Friedel-Crafts reaction.
(vi) Diazonium salts of aromatic amines are more stable than those of aliphatic amines. (vii) Gabriel phthalimide synthesis is preferred for synthesising primary amines.
Account for the following:
(i) pKb of aniline is more than that of methylamine.
(ii) Ethylamine is soluble in water whereas aniline is not.
(iii) Methylamine in water reacts with ferric chloride to precipitate hydrated ferric oxide.
(iv) Although amino group is o– and p– directing in aromatic electrophilic substitution reactions, aniline on nitration gives a substantial amount of m-nitroaniline.
(v) Aniline does not undergo Friedel-Crafts reaction.
(vi) Diazonium salts of aromatic amines are more stable than those of aliphatic amines. (vii) Gabriel phthalimide synthesis is preferred for synthesising primary amines.
Solution and Explanation
(i) pKb of aniline is more than that of methylamine:
Aniline undergoes resonance and as a result, the electrons on the N-atom are delocalized over the benzene ring. Therefore, the electrons on the N-atom are less available to donate.
On the other hand, in case of methylamine (due to the +I effect of methyl group), the electron density on the N-atom is increased. As a result, aniline is less basic than methylamine. Thus, pKb of aniline is more than that of methylamine.
(ii) Ethylamine is soluble in water whereas aniline is not: Ethylamine when added to water forms intermolecular H - bonds with water. Hence, it is soluble in water.
But aniline does not undergo H - bonding with water to a very large extent due to the presence of a large hydrophobic - C6H5 group. Hence, aniline is insoluble in water.
(iii) Methylamine in water reacts with ferric chloride to precipitate hydrated ferric oxide:
Due to the +I effect of - CH3 group, methylamine is more basic than water. Therefore, in water, methylamine produces OHions by accepting H+ ions from water.
Ferric chloride (FeCl3) dissociates in water to form Fe 3+ and Cl - ions.
Then, OHion reacts with Fe 3+ ion to form a precipitate of hydrated ferric oxide.
(iv) Although amino group is o,p - directing in aromatic electrophilic substitution reactions, aniline on nitration gives a substantial amount of m-nitroaniline: Nitration is carried out in an acidic medium. In an acidic medium, aniline is protonated to give anilinium ion (which is meta-directing).
For this reason, aniline on nitration gives a substantial amount of m-nitroaniline.
(v) Aniline does not undergo Friedel-Crafts reaction: A Friedel-Crafts reaction is carried out in the presence of AlCl3. But AlCl3 is acidic in nature, while aniline is a strong base. Thus, aniline reacts with AlCl3 to form a salt (as shown in the following equation).
Due to the positive charge on the N-atom, electrophilic substitution in the benzene ring is deactivated. Hence, aniline does not undergo the Friedel-Crafts reaction.
(vi) Diazonium salts of aromatic amines are more stable than those of aliphatic amines: The diazonium ion undergoes resonance as shown below:
This resonance accounts for the stability of the diazonium ion. Hence, diazonium salts of aromatic amines are more stable than those of aliphatic amines.
(vii) Gabriel phthalimide synthesis is preferred for synthesising primary amines: Gabriel phthalimide synthesis results in the formation of 1° amine only. 2° or 3° amines are not formed in this synthesis. Thus, a pure 1° amine can be obtained. Therefore, Gabriel phthalimide synthesis is preferred for synthesizing primary amines.
Top Questions on Amines
- Number of amine compounds from the following giving solids which are soluble in NaOH upon reaction with Hinsberg's reagent is _____.
- Number of compounds which give reaction with Hinsberg's reagent is_______.
- An amine $(\text{X})$ is prepared by ammonolysis of benzyl chloride. On adding $p$-toluenesulphonyl chloride to it, the solution remains clear.Molar mass of the amine $(\text{X})$ formed is _____ $\text{g mol}^{-1}$.(Given molar mass in $\text{g mol}^{-1}$: $\text{C} = 12, \, \text{H} = 1, \, \text{O} = 16, \, \text{N} = 14$)
- X of enthanamine was subjected to reaction with \(NaNO_2/HCl\) followed by hydrolysis to liberate \(N_2\) and HCl. The HCl generated was completely neutralised by 0.2 moles of NaOH. X is ____ g.
- Given below are two statements:
Statement (I) : All the following compounds react with p-toluenesulfonyl chloride.
$C_6H_5NH_2 \quad (C_6H_5)_2NH \quad (C_6H_5)_3N$
Statement (II) : Their products in the above reaction are soluble in aqueous NaOH.
In the light of the above statements, choose the correct answer from the options given below.
Questions Asked in CBSE CLASS XII exam
- Find the inverse of each of the matrices, if it exists. \(\begin{bmatrix} 1 & 3\\ 2 & 7\end{bmatrix}\)
- For what values of x,\(\begin{bmatrix} 1 & 2 & 1 \end{bmatrix}\)\(\begin{bmatrix} 1 & 2 & 0\\ 2 & 0 & 1 \\1&0&2 \end{bmatrix}\)\(\begin{bmatrix} 0 \\2\\x\end{bmatrix}\)=O?
- Find the inverse of each of the matrices,if it exists \(\begin{bmatrix} 2 & 1 \\ 7 & 4 \end{bmatrix}\)
What is the Planning Process?
- CBSE CLASS XII - 2023
- Planning process steps
- Find the inverse of each of the matrices,if it exists. \(\begin{bmatrix} 2 & 3\\ 5 & 7 \end{bmatrix}\)
Concepts Used:
Amines - Chemical Properties
There are many chemical properties of amines.
The primary and secondary amines, including several amine derivatives, have a direct impact on their properties due to the presence of hydrogen bonding. The compounds containing phosphorus have a lower boiling point and the compounds containing amines and alcohol have a higher boiling point. The structure of alkanols is immensely similar to that of amine except the presence of the hydroxyl group. In such a case, oxygen has a higher electronegativity than that of nitrogen, so alkanol compounds are more acidic in nature in comparison to the amines.
On account of the ability to form hydrogen bonds, the amines have tendencies of high solubility in water. The amine molecules such as Ethyl, diethyl, triethyl, and Methyl are gaseous in nature. Whereas, higher weight amines have a solid structure and alkyl amines have a liquid structure. There is an ammonia smell to gaseous amines and a fishy smell to liquid amines. The solubility of amines entirely depends upon the number of carbon atoms in the molecule.