Question

What will be the increasing order of basic strength of the following compounds: \(\text{C}_2\text{H}_5\text{NH}_2, (\text{C}_2\text{H}_5)_2\text{NH},(\text{C}_2\text{H}_5)_3\text{N},\text{C}_6\text{H}_5\text{NH}_2\)

• A. \(\text{C}_2\text{H}_5\text{NH}_2 < (\text{C}_2\text{H}_5)_2\text{NH} < (\text{C}_2\text{H}_5)_3\text{N} < \text{C}_6\text{H}_5\text{NH}_2\)
• B. \(\text{C}_6\text{H}_5\text{NH}_2 < \text{C}_2\text{H}_5\text{NH}_2 < (\text{C}_2\text{H}_5)_3\text{N} < (\text{C}_2\text{H}_5)_2\text{NH}\)
• C. \((\text{C}_2\text{H}_5)_3\text{N} < (\text{C}_2\text{H}_5)_2\text{NH} < \text{C}_6\text{H}_5\text{NH}_2 < \text{C}_2\text{H}_5\text{NH}_2\)
• D. \((\text{C}_2\text{H}_5)_2\text{NH} < (\text{C}_2\text{H}_5)_3\text{N} < \text{C}_2\text{H}_5\text{NH}_2 < \text{C}_6\text{H}_5\text{NH}_2\)

Answer 1

The Correct Option is B

To determine the increasing order of basic strength, we need to consider the factors that affect the basicity of amines:

1. Aliphatic vs. Aromatic Amines: Aliphatic amines (like C₂H₅NH₂, (C₂H₅)₂NH, (C₂H₅)₃N) are generally more basic than aromatic amines (like C₆H₅NH₂). This is because in aromatic amines, the lone pair of electrons on the nitrogen is delocalized into the benzene ring, making it less available for protonation.
2. Alkyl Groups: Alkyl groups are electron-donating, which increases the electron density on the nitrogen atom, making it more basic.
3. Steric Hindrance: In tertiary amines, the bulky alkyl groups can hinder the approach of a proton, reducing basicity.
4. Solvation Effects: In aqueous solutions, solvation of the protonated amine plays a significant role. Secondary amines are generally more solvated than tertiary amines.

 

Let's analyze the given compounds:

C₂H₅NH₂ (Ethylamine): A primary aliphatic amine.

(C₂H₅)₂NH (Diethylamine): A secondary aliphatic amine.

(C₂H₅)₃N (Triethylamine): A tertiary aliphatic amine.

C₆H₅NH₂ (Aniline): An aromatic amine.

Based on these factors:

Aniline (C₆H₅NH₂) is the least basic due to resonance delocalization.

Among the aliphatic amines, secondary amines are generally the most basic due to a combination of inductive and solvation effects.

Primary amines are less basic than secondary amines but more basic than tertiary amines due to steric hindrance in tertiary amines.

Therefore, the increasing order of basic strength is:

C₆H₅NH₂ < C₂H₅NH₂ < (C₂H₅)₃N < (C₂H₅)₂NH

 

The correct answer is:

Option 2: C₆H₅NH₂ < C₂H₅NH₂ < (C₂H₅)₃N < (C₂H₅)₂NH