Skip to main content
Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination
Mullins - Organic Chemistry: A Learner Centered Approach 1st Edition
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Not the one you use?Change textbook
Chapter 12, Problem 106o(ix,x)

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.'
(o) Chemical structure of a phenol with a hydroxyl group attached to a carbon chain.

Verified step by step guidance
1
Identify the functional group present in the given molecule. The structure shows a secondary alcohol attached to a benzene ring.
Understand the role of PCC (Pyridinium chlorochromate) in organic reactions. PCC is a mild oxidizing agent that typically oxidizes primary alcohols to aldehydes and secondary alcohols to ketones.
Predict the product of the reaction with PCC. Since the molecule contains a secondary alcohol, PCC will oxidize it to a ketone. The hydroxyl group (OH) will be converted to a carbonyl group (C=O).
Consider the reaction with H₂CrO₄ and H₂O. This is a stronger oxidizing agent compared to PCC and can further oxidize primary alcohols to carboxylic acids. However, secondary alcohols are oxidized to ketones, similar to PCC.
Conclude that both PCC and H₂CrO₄ will oxidize the secondary alcohol to a ketone, resulting in the same product for this specific molecule.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above.
Was this helpful?

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 oxidize primary alcohols to aldehydes and secondary alcohols to ketones without over-oxidation. It is less aggressive than other oxidants, making it suitable for sensitive substrates. Understanding its reactivity is crucial for predicting the products of reactions involving alcohols.
Recommended video:
Guided course
05:53
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. It is more powerful than PCC and can lead to complete oxidation of alcohols. Recognizing the strength of this oxidant helps in predicting the final products of reactions involving alcohols and their oxidation states.
Recommended video:
Guided course
02:10
DIBAL-H on Esters and Nitriles

Oxidation States and Functional Group Transformations

In organic chemistry, oxidation refers to the increase in oxidation state, often involving the addition of oxygen or the removal of hydrogen. Understanding how different functional groups transform under oxidation conditions is essential for predicting reaction outcomes. This includes recognizing when no reaction occurs, particularly with tertiary alcohols, which are resistant to oxidation.
Recommended video:
Guided course
02:36
Identifying Functional Groups