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)
(b) Sodium acetylide (NaC≡CH) or sodium amide (NaNH2)
(c) Sodium acetylide (NaC≡CH) or sodium ethoxide (NaOCH2CH3)
Sample Solution (a) NaOCH2CH3 contains the ions Na+ and CH3CH2O−. NaNH2contains the ions Na+ and H2N−. CH3CH2O− is the conjugate base of ethanol; H2N− is the conjugate base of ammonia.
Base | CH3CH2O− | H2N− |
Conjugate acid | CH3CH2OH | NH3 |
pKa of conjugate acid | 16 | 36 |
The conjugate acid of CH3CH2O− is stronger than the conjugate acid of H2N−. Therefore, H2N− is a stronger base than CH3CH2O−.
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