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The increasing order of basicity for the following intermediates is (from weak to strong) (i) (CH3)3C⊖ (ii) H2C = CH – CH2⊖ (iii) HC ≡ C⊖ (iv) CH3⊖ (v) CN⊖

1. (v) < (iii) < (ii) < (iv) < (i)
2. (iii) < (i) < (ii) < (iv) < (v)
3. (v) < (i) < (iv) < (ii) < (iii)
4. (iii) < (iv) < (ii) < (i) < (v)

Correct answer: (iii) < (iv) < (ii) < (i) < (v)

Solution

The correct order reflects the stability of the corresponding anions; the more stable the anion, the weaker its basicity. The anion HC≡C⊖ is the least stable due to its high electronegativity and sp hybridization, while CN⊖ is the most stable due to resonance and electronegativity, making it the strongest base.

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