Question

what alcohol would be oxidized to form the compound below? none of the reactants listed would form the compound shown.

Explanation:

Step1: Recall oxidation of alcohols

Primary alcohols are oxidized to aldehydes and then to carboxylic - acids. Secondary alcohols are oxidized to ketones. Tertiary alcohols are not easily oxidized. The given compound is a carboxylic acid. It is formed by the oxidation of a primary alcohol.

Step2: Analyze each option

• For $CH_3(CH_2)_5CH_2OH$, it is a straight - chain primary alcohol and will not form the branched - chain carboxylic acid shown.
• For

$$\begin{array}{c}CH_3\\|\\CH_3 - C - CH_2 - OH\\|\\CH_2CH_2CH_3\end{array}$$

, it is a primary alcohol. Oxidation of this primary alcohol will first form an aldehyde and then a carboxylic acid with the same carbon - chain structure as the original alcohol.

• For

$$\begin{array}{c}CH_3\\|\\CH_3 - CH - CH - OH\\|\\CH_2CH_2CH_3\end{array}$$

, it is a secondary alcohol and will be oxidized to a ketone, not a carboxylic acid.

• For

$$\begin{array}{c}OH\\|\\CH_3 - C - CH_2 - CH_3\\|\\CH_2CH_2CH_3\end{array}$$

, it is a tertiary alcohol and is not easily oxidized to a carboxylic acid.

Answer:

$$\begin{array}{c}CH_3\\|\\CH_3 - C - CH_2 - OH\\|\\CH_2CH_2CH_3\end{array}$$