Which is the stronger base in each of the following pairs? (Note: This information will pr...

Which is the stronger base in each of the following pairs? (Note: This information will prove useful when you get to Chapter 9.)

(a) Sodium ethoxide (NaOCH₂CH₃) or sodium amide (NaNH₂)

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(b) Sodium acetylide or sodium amide (NaNH₂)

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(c) Sodium acetylide or sodium ethoxide (NaOCH₂CH₃)

Sample Solution (a) NaOCH₂CH₃ contains the ions Na⁺ and CH₃CH₂O⁻. NaNH₂ contains the ions Na⁺ and H₂N⁻. CH₃CH₂O⁻ is the conjugate base of ethanol; H₂N⁻ is the conjugate base of ammonia.

The conjugate acid of CH₃CH₂O⁻ is stronger than the conjugate acid of H₂N^–. Therefore, H₂N⁻ is a stronger base than CH₃CH₂O⁻.