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Baeyer-Villiger Oxidation & Rearrangement | Chemistry Optional Notes for UPSC PDF Download
| Table of contents |
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| Definition: What is Baeyer-Villiger Oxidation? |
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| Examples of Baeyer-Villiger Oxidation |
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| Mechanism of Baeyer-Villiger Oxidation |
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| Baeyer-Villiger Rearrangement |
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Definition: What is Baeyer-Villiger Oxidation?
The Baeyer-Villiger oxidation is the oxidative cleavage of a carbon-carbon bond that is adjacent to a carbonyl functional group. This reaction is used to convert ketones to esters and cyclic ketones to lactones. It can be carried out with peroxy acids (also called peracid) like MCPBA, or with hydrogen peroxide and a Lewis acid. This reaction can be viewed as the insertion of O into one of the C-C bonds adjacent to the carbonyl functional group. For non-symmetrical cyclic ketones, the more highly substituted alkyl group migrates and becomes attached to the inserted O atom.
The history of this reaction goes back to 1899 when German chemists Adolf von Baeyer and Victor Villiger reported it.
Examples of Baeyer-Villiger Oxidation
Baeyer-Villiger oxidation is used in the synthesis of caprolactone from cyclohexanone.
Mechanism of Baeyer-Villiger Oxidation
In this reaction, the ketone is oxidized, whereas the peroxy acid is reduced.
Question for Baeyer-Villiger Oxidation & RearrangementTry yourself: Which of the following is the product of Baeyer-Villiger oxidation?View Solution
Application of Baeyer-Villiger Oxidation
Baeyer-Villiger oxidation is used in the synthesis of lactones, which contribute significantly to the flavor of fruits, and unfermented and fermented dairy products. Hence, they are used for flavor and fragrance. Polycaprolactone is a biodegradable polyester from which polyurethane is made.
Baeyer-Villiger Rearrangement
The Baeyer-Villiger rearrangement is the conversion of a ketone to an ester via the insertion of an oxygen atom next to the carbonyl.
The reaction involves initial addition of a peroxide to the carbonyl carbon. The resulting adduct undergoes rearrangement to form the ester.
Solved Examples
Example: Predict the products of the following Baeyer-Villiger reactions.
Ans:
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FAQs on Baeyer-Villiger Oxidation & Rearrangement - Chemistry Optional Notes for UPSC
| 1. What is Baeyer-Villiger Oxidation? |  |
Ans. Baeyer-Villiger oxidation is a chemical reaction in which a ketone or aldehyde is converted into an ester or lactone, respectively, by the reaction with a peracid. This reaction involves the migration of an alkyl or aryl group from the carbonyl carbon to an adjacent carbon, resulting in the formation of a new C-O bond.
| 2. Can you provide examples of Baeyer-Villiger Oxidation? | |
Ans. Yes, here are some examples of Baeyer-Villiger oxidation:
- Conversion of cyclobutanone to cyclobutanone peroxide, which upon hydrolysis gives the corresponding lactone.
- Oxidation of benzaldehyde to benzoyl peroxide, which upon hydrolysis gives the corresponding ester.
- Conversion of acetophenone to phenyl acetate, which upon hydrolysis gives the corresponding ester.
| 3. What is the mechanism of Baeyer-Villiger Oxidation? | |
Ans. The mechanism of Baeyer-Villiger oxidation involves the formation of a peracid intermediate, which acts as an electrophile. The carbonyl oxygen of the ketone or aldehyde attacks the peracid, leading to the formation of an intermediate called an acylperoxyacid. This intermediate then undergoes rearrangement, involving migration of an alkyl or aryl group from the carbonyl carbon to an adjacent carbon. Finally, the rearranged intermediate is hydrolyzed to yield the ester or lactone product.
| 4. What is Baeyer-Villiger rearrangement? | |
Ans. Baeyer-Villiger rearrangement is a related reaction to Baeyer-Villiger oxidation. In this rearrangement, a cyclic ketone or aldehyde is converted into a cyclic ester or lactone, respectively. The rearrangement involves the migration of an alkyl or aryl group from the carbonyl carbon to an adjacent carbon, resulting in the formation of a new C-O bond. The rearrangement can be achieved by treating the cyclic ketone or aldehyde with a peracid or by using other oxidizing agents.
| 5. How is Baeyer-Villiger Oxidation relevant to the UPSC exam? | |
Ans. Baeyer-Villiger oxidation is a concept in organic chemistry that is relevant to the UPSC exam for candidates appearing for the chemistry paper. Understanding the mechanism and applications of Baeyer-Villiger oxidation can help in solving related questions on oxidation reactions, functional group transformations, and organic synthesis. Additionally, knowledge of Baeyer-Villiger oxidation can be useful in understanding the reactivity and transformations of carbonyl compounds, which are commonly encountered in organic chemistry.
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Nov 24, 2024 Last updated |
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