Question

what alcohol would be oxidized to form the compound below? ch3 - c(ch3)(ch2ch2ch3)-c - oh ch3(ch2)5ch2oh ch3 - c(ch3)(ch2ch2ch3)-ch2 - oh ch3 - ch(ch3)-ch(ch2ch2ch3)-oh ch3 - c(oh)(ch2ch2ch3)-ch2 - ch3

Explanation:

Step1: Recall oxidation of alcohols

Primary alcohols are oxidized to aldehydes first and then to carboxylic - acids. Secondary alcohols are oxidized to ketones. Tertiary alcohols are not easily oxidized. The given compound is a carboxylic acid. So, it must be formed from the oxidation of a primary alcohol.

Step2: Analyze the structure of the carboxylic - acid

The structure of the given carboxylic acid has a carbon - chain with a specific branching. The carbonyl carbon of the carboxylic acid was the $-CH_2OH$ group in the original alcohol.

Step3: Match the structure of the alcohol

The correct alcohol should have the same carbon - skeleton as the carboxylic acid with a $-CH_2OH$ group at the end of the chain that will be oxidized to the $-COOH$ group. The alcohol $CH_3 - C(CH_3)(CH_2CH_2CH_3)-CH_2OH$ will be oxidized to the given carboxylic acid.

Answer:

The second option (the alcohol with the structure $CH_3 - C(CH_3)(CH_2CH_2CH_3)-CH_2OH$)