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Related Concept Videos

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

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.
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
Hydroboration-Oxidation of Alkenes03:08

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.
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is confirmed through isotopic...
Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule02:17

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...

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Updated: Jun 8, 2026

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
07:06

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

Published on: February 16, 2020

Alkene hydroboration: hot intermediates that react while they are cooling.

David R Glowacki1, C H Liang, Stephen P Marsden

  • 1School of Chemistry, University of Leeds, Leeds LS2 9JT, United Kingdom. david.r.glowacki@bristol.ac.uk

Journal of the American Chemical Society
|September 14, 2010
PubMed
Summary
This summary is machine-generated.

Non-statistical behavior in chemical reactions challenges traditional models. This study uses a master equation model to show that even in solution, hot intermediates can react before full thermalization, preserving statistical models.

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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
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Published on: November 30, 2022

Area of Science:

  • Physical Chemistry
  • Organic Chemistry
  • Chemical Dynamics

Background:

  • Non-statistical behavior in chemical reactions is gaining attention.
  • Departures from Transition State Theory (TST) predictions challenge standard chemical reactivity models.

Purpose of the Study:

  • To propose an alternative interpretation of experimental results for hydroboration mechanisms.
  • To investigate the role of non-statistical dynamical effects versus statistical reaction models.

Main Methods:

  • Utilized a weak collision Rice-Ramsperger-Kassel-Marcus (RRKM)-Master Equation (ME) model for calculations.
  • Applied master equation methodology to a solution-phase thermal reaction.

Main Results:

  • Demonstrated that "hot" intermediates can react during stepwise relaxation via weak collisions in solution.
  • Provided a statistical interpretation of experimental results that deviate from TST predictions.
  • Showcased the master equation as a computationally tractable model for solution-phase reactions.

Conclusions:

  • The master equation offers a viable alternative to conventional TST for explaining certain organic reaction mechanisms.
  • Stepwise collisional relaxation of intermediates may be prevalent in various polyatomic systems.
  • This work provides a new computational approach for studying chemical reaction dynamics in solution.