Textbook Question
Draw a mechanism for the following oxidation reactions.
(c)
13. Alcohols and Carbonyl Compounds
Oxidizing Agent
Problem 106f(ix,x)
Textbook Question
Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (ix) PCC; (x) H₂CrO₄ , H₂O If no reaction occurs, write 'no reaction.'
(f) 
Verified step by step guidance1
Identify the structure of the given molecule. The image shows a tertiary alcohol, specifically 2-methyl-2-phenylpropan-2-ol.
Understand the reagents: PCC (Pyridinium chlorochromate) is a mild oxidizing agent that typically oxidizes primary alcohols to aldehydes and secondary alcohols to ketones. H₂CrO₄ (chromic acid) is a strong oxidizing agent that can oxidize primary alcohols to carboxylic acids and secondary alcohols to ketones.
Recognize that tertiary alcohols, like the one in the image, generally do not undergo oxidation with either PCC or H₂CrO₄ because there is no hydrogen atom on the carbon bearing the hydroxyl group to be removed during the oxidation process.
Predict the outcome for reaction (ix) with PCC: Since the molecule is a tertiary alcohol, no reaction will occur because PCC cannot oxidize tertiary alcohols.
Predict the outcome for reaction (x) with H₂CrO₄, H₂O: Similarly, no reaction will occur with H₂CrO₄ as it also cannot oxidize tertiary alcohols.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
PCC (Pyridinium Chlorochromate)
PCC is a mild oxidizing agent commonly used in organic chemistry to convert primary alcohols to aldehydes and secondary alcohols to ketones without over-oxidation. It is favored for its ability to selectively oxidize alcohols while minimizing side reactions, making it useful in synthetic pathways where specific functional groups need to be preserved.
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Strong oxidizing agents
H₂CrO₄ (Chromic Acid)
H₂CrO₄ is a strong oxidizing agent that can oxidize primary alcohols to carboxylic acids and secondary alcohols to ketones. Its reactivity is higher than that of PCC, which means it can lead to over-oxidation if not controlled. Understanding its reactivity is crucial for predicting the outcomes of reactions involving alcohols and other functional groups.
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Oxidation States and Functional Group Transformations
In organic chemistry, oxidation refers to the increase in oxidation state of a molecule, often involving the addition of oxygen or the removal of hydrogen. Recognizing how different reagents affect the oxidation states of functional groups is essential for predicting reaction products. This concept helps in understanding how alcohols can be transformed into aldehydes, ketones, or carboxylic acids depending on the oxidizing agent used.
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