Organic Chemistry : Using Other Organic Oxidizing Agents

Study concepts, example questions & explanations for Organic Chemistry

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Example Questions

Example Question #1 : Using Other Organic Oxidizing Agents

Which of the following reagents can turn primary alcohols into a carboxylic acid?

Possible Answers:

Jones Reagent (chromic acid in acetone)

PCC

Tollen's test

Correct answer:

Jones Reagent (chromic acid in acetone)

Explanation:

The Jones reagent can convert primary alcohol to acids and secondary alcohols to ketones. The Tollen's test only converts aldehydes to carboxylic acids. PCC can only convert primary and secondary alcohol to aldehydes and ketones, respectively.  and  are reducing agents. 

Example Question #2 : Using Other Organic Oxidizing Agents

What is an appropriate reagent to convert a primary alcohol to an aldehyde? 

Possible Answers:

Correct answer:

Explanation:

To form the aldehyde, the alcohol must be oxidized. However, potassium permanganate and chromic acid are too strong and would yield a carboxylic acid. Ozonolysis works with alkenes and oxygen over platinum would not react. PCC is correct because it will oxidize the alcohol to form an aldehyde but is too weak to continue on to form the carboxylic acid.

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