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Oxidative Cleavage of Alkenes: Ozonolysis

Oxidative Cleavage of Alkenes: Ozonolysis

In ozonolysis, ozone is used to cleave a carbon–carbon double bond to form aldehydes and ketones, or carboxylic acids, depending on the work-up.
Ozone is a symmetrical bent molecule stabilized by a resonance structure.

Hydroboration-Oxidation of Alkenes

Hydroboration-Oxidation of Alkenes

In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.

Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation

Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation

Baeyer–Villiger oxidation converts aldehydes to carboxylic acids and ketones to esters. The reaction uses peroxy acids or peracids and is often catalyzed by acid. The reaction is named after its pioneers, Adolf von Baeyer and Victor Villiger. The reaction is achieved by a wide range of peracids such as m-chloroperoxybenzoic acid (mCPBA), perbenzoic acid (C6H5COOOH), peracetic acid (CH3COOOH), hydrogen peroxide (H2O2), and tert-butyl hydroperoxide (t-BuOOH).
The carbonyl center is...

Alkynes to Carboxylic Acids: Oxidative Cleavage

Alkynes to Carboxylic Acids: Oxidative Cleavage

Alkynes undergo oxidative cleavage in the presence of oxidizing reagents like potassium permanganate and ozone. The triple bond — one σ bond and two π bonds — is completely cleaved, and the alkyne is oxidized to carboxylic acids. When warm and basic aqueous potassium permanganate is used as an oxidizing agent, alkynes are first converted to carboxylate salts via an unstable α-diketone intermediate. Further, a mild acid treatment protonates the carboxylate anions...

Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate

Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate

Alkenes can be dihydroxylated using potassium permanganate. The method encompasses the reaction of an alkene with a cold, dilute solution of potassium permanganate under basic conditions to form a cis-diol along with a brown precipitate of manganese dioxide.

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A Toolkit to Enable Hydrocarbon Conversion in Aqueous Environments

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Published on: October 2, 2012

Structure and Function of Alkane Monooxygenase (AlkB).

John T Groves¹, Liang Feng², Rachel Narehood Austin³

¹Department of Chemistry, Princeton University, Princeton, New Jersey 08544, United States.

Accounts of Chemical Research

|November 30, 2023

Summary

Researchers investigated the structure and mechanism of alkane monooxygenase (AlkB), a key enzyme in hydrocarbon degradation. This study provides new insights into how AlkB activates and transforms liquid alkanes in the environment.

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Area of Science:

Biochemistry
Environmental Microbiology

Background:

Hydrocarbons, particularly alkanes, are abundant environmental pollutants.
Organisms transform alkanes for energy and carbon, utilizing both aerobic and anaerobic pathways.
Understanding alkane-transforming enzymes is crucial for bioremediation and the carbon cycle.

Approach:

Focuses on the alkane monooxygenase (AlkB) enzyme, responsible for aerobic liquid alkane transformation.
Reviews recent high-resolution cryo-electron microscopy (cryo-EM) structures of AlkB.
Integrates functional studies, radical clock assays, and comparative analysis with related enzymes.

Key Points:

The first structures of AlkB, a predominant aerobic alkane hydroxylase, were determined in 2023.
Functional studies of single residue variants reveal how AlkB's structure facilitates its catalytic activity.
Mechanistic studies using radical clock substrates characterize AlkB's reaction pathway.

Conclusions:

Provides a holistic understanding of AlkB by integrating structural, functional, and mechanistic data.
Highlights similarities and differences with other diiron enzymes.
Identifies outstanding questions regarding the enzyme's active site electronic structure and broader biological roles.