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Why tertiary alcohol reacts with metallic sodium less rapidly than primary alcohol?
Wiki User
∙ 11y ago
Tertiary acids are less acidic than primary alcohols (which are, themselves, not usually all that acidic).
This is because of increased electron density on the oxygen atom of the tertiary alcohol, and also steric hindrance for solvation of the resultant alkoxide ion.
The net effect is that tertiary alcohols generally tend to "hold on" to their alcoholic hydrogen more tightly than primary alcohols.
Wiki User
∙ 11y ago
Tertiary alcohols have a bulky alkyl group bonded to the carbon atom that carries the hydroxyl group. This bulky group hinders the approach of the sodium atom, making the reaction less rapid. In contrast, primary alcohols have a smaller alkyl group and allow for easier access and reaction with metallic sodium.
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