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Radical Formation: Homolysis00:54

Radical Formation: Homolysis

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A bond is formed between two atoms by sharing two electrons. When this bond is broken by supplying sufficient energy, either two electrons can be taken up by one atom forming ions by the cleavage called heterolysis, or the two electrons are shared by two atoms, with one each creating radicals by the cleavage called homolysis.
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Hydroboration-Oxidation of Alkenes03:08

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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.
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Radical Formation: Elimination00:51

Radical Formation: Elimination

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Another method of radical formation is the elimination process. It is the opposite of the addition route and is driven by the instability of the radical. For example, as depicted in Figure 1, dibenzoyl peroxide yields a pair of unstable radicals upon homolysis. Given its instability, this radical spontaneously undergoes elimination via a C–C bond cleavage to form a relatively more stable phenyl radical. The mechanism involves cleavage of the bond between the α and β positions with respect...
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Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

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Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...
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Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

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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.
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Ethylene decomposition on Ir(111): initial path to graphene formation.

Holly Tetlow1, Joel Posthuma de Boer2, Ian J Ford3

  • 1Physics Department, King's College London, London, WC2R 2LS, UK. lev.kantorovitch@kcl.ac.uk.

Physical Chemistry Chemical Physics : PCCP
|October 7, 2016
PubMed
Summary
This summary is machine-generated.

This study reveals the complete mechanism of ethylene decomposition on Ir(111) for graphene growth. It details the step-by-step conversion of ethylene to carbon monomers via surface species, crucial for graphene nucleation.

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Area of Science:

  • Surface science
  • Chemical kinetics
  • Materials science

Background:

  • Graphene growth on transition metals is vital for electronic applications.
  • Understanding the initial steps of graphene formation is key to controlling its quality.
  • Ethylene (C2H4) decomposition on iridium (Ir(111)) is a critical initial step in graphene synthesis.

Purpose of the Study:

  • To elucidate the complete thermal decomposition mechanism of ethylene on Ir(111).
  • To identify and track surface species during ethylene decomposition.
  • To establish the reaction pathway from ethylene to carbon monomers for graphene nucleation.

Main Methods:

  • Combined experimental techniques, including high-resolution X-ray photoelectron spectroscopy (HRXPS).
  • Theoretical calculations using ab initio density functional theory (DFT) for energy barriers and reaction pathways.
  • Kinetic simulations based on calculated reaction parameters to model species evolution.

Main Results:

  • Identified surface species and their temperature-dependent evolution during ethylene decomposition.
  • Established a detailed reaction sequence from ethylene to C monomers and dimers.
  • Validated simulated kinetics against experimental photoemission measurements.
  • Observed key intermediates: vinylidene (CH2C), acetylene (CHCH), methylidyne (CH), and ethylidyne (CH3C).

Conclusions:

  • The study provides the first complete mechanism for ethylene thermal decomposition on Ir(111).
  • The identified pathway details the sequential dehydrogenation and C-C bond breaking leading to carbon monomers.
  • These carbon monomers are essential for the initial nucleation of graphene islands on the Ir(111) surface.