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Basics of Organic Chemistry question

2023 · 25 Jan · Shift 1 · Q12
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Basics of Organic Chemistry question

2023 · 25 Jan · Shift 1 · Q12

JEE MainChemistryBasics of Organic ChemistryMCQ+4 / −1
The correct order in aqueous medium of basic strength in case of methyl substituted amines is :
  1. A
    NH3>Me3N>MeNH2>Me2NH\mathrm{NH_3 \gt Me_3N \gt MeNH_2 \gt Me_2NH}NH3​>Me3​N>MeNH2​>Me2​NH
  2. B
    Me3N>Me2NH>MeNH2>NH3\mathrm{Me_3N \gt Me_2NH \gt MeNH_2 \gt NH_3}Me3​N>Me2​NH>MeNH2​>NH3​
  3. C
    Me2NH>MeNH2>Me3N>NH3\mathrm{Me_2NH \gt MeNH_2 \gt Me_3N \gt NH_3}Me2​NH>MeNH2​>Me3​N>NH3​
  4. D
    Me2NH>Me3N>MeNH2>NH3\mathrm{Me_2NH \gt Me_3N \gt MeNH_2 \gt NH_3}Me2​NH>Me3​N>MeNH2​>NH3​
View written solutionFree

Correct answer: C

  1. Basic strength in aqueous medium depends on two main factors:

    • +I+I+I effect of alkyl groups, which increases electron density on nitrogen and tends to increase basicity.
    • Solvation of the conjugate acid in water, which stabilizes the protonated amine. Better solvation means greater basic strength in aqueous medium.
  2. For methyl-substituted amines:

    • MeNH2\mathrm{MeNH_2}MeNH2​ (primary amine)
    • Me2NH\mathrm{Me_2NH}Me2​NH (secondary amine)
    • Me3N\mathrm{Me_3N}Me3​N (tertiary amine)

    Although tertiary amine has the strongest +I+I+I effect, its protonated form is poorly solvated due to steric hindrance.

  3. In aqueous solution, the usual order of basic strength of aliphatic amines is: 2∘>1∘>3∘>NH3\mathrm{2^\circ > 1^\circ > 3^\circ > NH_3}2∘>1∘>3∘>NH3​

  4. Applying this to methyl amines: Me2NH>MeNH2>Me3N>NH3\mathrm{Me_2NH > MeNH_2 > Me_3N > NH_3}Me2​NH>MeNH2​>Me3​N>NH3​

  5. Now check the options:

    • A: NH3>Me3N>MeNH2>Me2NH\mathrm{NH_3 > Me_3N > MeNH_2 > Me_2NH}NH3​>Me3​N>MeNH2​>Me2​NH ❌ incorrect
    • B: Me3N>Me2NH>MeNH2>NH3\mathrm{Me_3N > Me_2NH > MeNH_2 > NH_3}Me3​N>Me2​NH>MeNH2​>NH3​ ❌ incorrect
    • C: Me2NH>MeNH2>Me3N>NH3\mathrm{Me_2NH > MeNH_2 > Me_3N > NH_3}Me2​NH>MeNH2​>Me3​N>NH3​ ✅ correct
    • D: Me2NH>Me3N>MeNH2>NH3\mathrm{Me_2NH > Me_3N > MeNH_2 > NH_3}Me2​NH>Me3​N>MeNH2​>NH3​ ❌ incorrect
  6. Therefore, the correct order is: Me2NH>MeNH2>Me3N>NH3\boxed{\mathrm{Me_2NH > MeNH_2 > Me_3N > NH_3}}Me2​NH>MeNH2​>Me3​N>NH3​​

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