Q26 / 150 · MHT CET 2025 (22 Apr Shift 1) · Chemistry

Identify strongest base from following.

  • A
    $\mathrm{NH}_3$
  • B
    $\mathrm{CH}_3 \mathrm{NH}_2$
  • Correct answer
    C
    $\left(\mathrm{CH}_3\right)_2 \mathrm{NH}$
  • D
    $\left(\mathrm{CH}_3\right)_3 \mathrm{~N}$

Solution

Base strength in aqueous solution depends on the balance between inductive effects, steric hindrance, and solvation stability.

Alkyl groups donate electron density through the $+I$ effect, increasing nitrogen's basicity. However, larger alkyl groups introduce steric hindrance and reduce conjugate acid solvation through hydrogen bonding.

For methyl-substituted amines: $(\mathrm{CH}_3)_2\mathrm{NH}$ provides optimal balance with strong inductive effect from two methyl groups, moderate steric hindrance, and adequate solvation of its conjugate acid $(\mathrm{CH}_3)_2\mathrm{NH}_2^+$ which forms two hydrogen bonds.

$\mathrm{CH}_3\mathrm{NH}_2$ has weaker inductive effect and $\mathrm{NH}_3$ has no alkyl groups, while $(\mathrm{CH}_3)_3\mathrm{N}$ suffers from significant steric hindrance and poor solvation of its conjugate acid.

The basicity order is secondary $>$ primary $>$ tertiary $>$ ammonia, making $(\mathrm{CH}_3)_2\mathrm{NH}$ the strongest base.

Hence, the correct answer is option: 'C'.

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