MCQEasyJEE 2023Amines (Classification & Properties)

JEE Chemistry 2023 Question with Solution

The correct order in aqueous medium of basic strength in case of methyl-substituted amines is:

  • A

    Me2NH>MeNH2>Me3N>NH3\mathrm{Me}_2\mathrm{NH} > \mathrm{MeNH}_2 > \mathrm{Me}_3\mathrm{N} > \mathrm{NH}_3

  • B

    Me2N>Me3NH>MeNH2>NH3\mathrm{Me}_2\mathrm{N} > \mathrm{Me}_3\mathrm{NH} > \mathrm{MeNH}_2 > \mathrm{NH}_3

  • C

    NH3>Me3N>MeNH2>Me2NH\mathrm{NH}_3 > \mathrm{Me}_3\mathrm{N} > \mathrm{MeNH}_2 > \mathrm{Me}_2\mathrm{NH}

  • D

    Me3N>Me2NH>MeNH2>NH3\mathrm{Me}_3\mathrm{N} > \mathrm{Me}_2\mathrm{NH} > \mathrm{MeNH}_2 > \mathrm{NH}_3

Answer

Correct answer:A

Step-by-step solution

Standard Method

Given: The order of basic strength in aqueous medium for methyl-substituted amines is to be identified.

Find: The correct order among the given options.

In aqueous medium, the basic strength of amines depends on:

  1. Electron density on the nitrogen atom due to the inductive effect of methyl groups.
  2. Solvation effect, which stabilizes the conjugate acid after accepting a proton.
  • Dimethylamine Me2NH\mathrm{Me}_2\mathrm{NH}: The best combination of inductive effect and solvation, making it the most basic.
  • Methylamine MeNH2\mathrm{MeNH}_2: Slightly less basic due to less inductive effect but better solvation.
  • Trimethylamine Me3N\mathrm{Me}_3\mathrm{N}: Weaker basicity because bulky groups hinder solvation.
  • Ammonia NH3\mathrm{NH}_3: Lowest basicity due to the absence of inductive effect.

Therefore, the order is

Me2NH>MeNH2>Me3N>NH3\mathrm{Me}_2\mathrm{NH} > \mathrm{MeNH}_2 > \mathrm{Me}_3\mathrm{N} > \mathrm{NH}_3

So, the correct option according to the extracted working is A.

Note: The solution says "The Correct Option is C", but the worked explanation clearly concludes the order matching Option A. Hence the worked solution is taken as authoritative.

Common mistakes

  • Assuming stronger +I effect alone decides basicity in water is incorrect. In aqueous medium, solvation of the conjugate acid also matters. Always consider both inductive effect and solvation together.

  • Placing Me3N\mathrm{Me}_3\mathrm{N} above MeNH2\mathrm{MeNH}_2 only because it has more methyl groups is wrong. Steric hindrance reduces solvation of the protonated species. Account for poor solvation of tertiary amines in water.

  • Treating gaseous-phase basicity and aqueous basicity as the same leads to error. The aqueous order is strongly affected by solvation, so do not use gas-phase intuition directly.

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