KCET · Chemistry · Amines

Arrange the following in the increasing order of their basic strengths \(\mathrm{CH}_{3} \mathrm{NH}_{2},\left(\mathrm{CH}_{3}\right)_{2} \mathrm{NH}\), \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{~N}, \mathrm{NH}_{3}\)

A \(\mathrm{NH}_{3} < \left(\mathrm{CH}_{3}\right)_{3} \mathrm{~N} < \left(\mathrm{CH}_{3}\right)_{2} \mathrm{NH} < \mathrm{CH}_{3} \mathrm{NH}_{2}\)
B \(\mathrm{NH}_{3} < \left(\mathrm{CH}_{3}\right)_{3} \mathrm{~N} < \mathrm{CH}_{3} \mathrm{NH}_{2} < \left(\mathrm{CH}_{3}\right)_{2} \mathrm{NH}\)
C \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{~N} < \mathrm{NH}_{3} < \mathrm{CH}_{3} \mathrm{NH}_{2} < \left(\mathrm{CH}_{3}\right)_{2} \mathrm{NH}\)
D \(\mathrm{CH}_{3} \mathrm{NH}_{2} < \left(\mathrm{CH}_{3}\right)_{2} \mathrm{NH} < \left(\mathrm{CH}_{3}\right)_{3} \mathrm{~N} < \mathrm{NH}_{3}\)

Verified Solution

Answer & Solution

Correct Answer

(B) \(\mathrm{NH}_{3} < \left(\mathrm{CH}_{3}\right)_{3} \mathrm{~N} < \mathrm{CH}_{3} \mathrm{NH}_{2} < \left(\mathrm{CH}_{3}\right)_{2} \mathrm{NH}\)

Step-by-step Solution

Detailed explanation

Aliphatic amines are more basic than \(\mathrm{NH}_{3}\) due to \(+I\) effect of alkyl groups. In aqueous medium tertiary amine is less basic than secondary amine because the cation formed by protonation of tertiary amine is less solvated as compared to the cation formed by protonation of secondary amine. Hence, the increasing order of their basic strength is as:
\[
\mathrm{NH}_{3} < \left(\mathrm{CH}_{3}\right)_{3} \mathrm{~N} < \mathrm{CH}_{3} \mathrm{NH}_{2} < \left(\mathrm{CH}_{3}\right)_{2} \mathrm{NH}
\]

Apply the relevant identity from the chapter and substitute the values established in the previous step, keeping the original constraint in view.

Use the simplified expression to isolate the unknown, then plug the result back into the question setup to confirm the working is internally consistent.

Cross-check against a boundary or limiting case. Both the dimensional balance and the qualitative behaviour at the extreme should agree with the candidate answer.

Combine the steps above to identify the correct option. The remaining choices each fail at least one of the consistency, dimensional, or boundary checks.

Same subject

Explore more questions on app

From KCET

Explore more questions on app