Question

Write the structural formula and IUPAC name of the alcohol having molecular formula C\(_4\)H\(_{10}\)O which does not undergo oxidation under normal condition.

Hint:

The reactivity of alcohols to oxidation is a key way to distinguish them: - \textbf{Primary (1\(^\circ\)) alcohols} oxidize to aldehydes, then to carboxylic acids. - \textbf{Secondary (2\(^\circ\)) alcohols} oxidize to ketones. - \textbf{Tertiary (3\(^\circ\)) alcohols} resist oxidation under normal conditions.

Answer 1

An alcohol that does not undergo oxidation under normal conditions must be a tertiary alcohol. This is because a tertiary alcohol has no hydrogen atom attached to the carbinol carbon (the carbon atom bonded to the -OH group).
For the molecular formula C\(_4\)H\(_{10}\)O, the tertiary alcohol is 2-methylpropan-2-ol.
Structural Formula: \[ \begin{array}{c} \phantom{\text{H}_3\text{C}-} \text{CH}_3 \\ \phantom{\text{H}_3\text{C}-} | \\ \text{H}_3\text{C} - \text{C} - \text{OH} \\ \phantom{\text{H}_3\text{C}-} | \\ \phantom{\text{H}_3\text{C}-} \text{CH}_3 \end{array} \]
IUPAC Name: The longest carbon chain containing the -OH group has three carbons (propane). The -OH group is on carbon 2, and a methyl group is also on carbon 2.
Therefore, the name is 2-methylpropan-2-ol.