Questions tagged [radicals]

Radicals are highly reactive species, that have one or more unpaired electrons. Whether a species has unpaired electron(s) can be experimentally determined through electron pair resonance spectroscopy. Radicals are paramagnetic. This tag should be applied to questions that involve free radicals as a species or radicals in reactions and their mechanisms.

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Bromine Homolysis Using Handheld UV Lamp

I'm trying to investigate the homolysis of bromine for an IB Chemistry (high school) Internal Assessment. To do so, I need a UV lamp capable of splitting diatomic bromine into bromine radicals. Would ...
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937 views

Radical Bromination of a 1-isopropyl-4-methylcyclohexane

I'm considering a problem whereby 1-isopropyl-4-methylcyclohexane with the indicated stereochemistry shown undergoes radical bromination at the indicated position. I understand there are other ...
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Terminology for “proton stripping”?

This is going to probably be an easy question for an organic chemist, but I am looking for the proper terminology to describe the following reaction mechanism. In particular, what is a more precise ...
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Do free radicals re-arrange? [duplicate]

For example reaction of but-1-ene in the presence of $\ce{Br2}$ and light should give 1-bromobut-2-ene which is thermodynamically more stable than 3-bromobut-1-ene on the basis of number of alpha ...
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Why won't ethene and ethyne react with halogens?

With alkanes, a free-radical halogenation (substitution) is observed. I was told that there will be no reaction in a similar situation with ethene and ethyne — and I am having trouble understanding ...
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303 views

Anti-Markovnikov Effect

We have seen that $\ce{HBr}$ shows an anti-Markovnikov effect when it reacts with alkenes in the presence of peroxides. Why does only $\ce{HBr}$ shows this effect? How about the other hydrogen halides ...
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Which C-C bond would break first, the one in ethane, or 2,2-dimethylpropane?

I have drawn the figures and determined intuitively that the larger molecule's $\ce{C-C}$ would break first. I made this assumption that ethane has the stronger $\ce{C-C}$ bond and I am correct, ...
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660 views

What is the state of the oxygen free radical in the following reaction?

$$\ce{O2(g) ->[h\nu][\nu\,<\,240~nm]2O^{.}(?)}$$ Oxygen is split by UV light below 240 nm to form oxygen radicals, which then go on to react with oxygen molecules to form ozone. Firstly, is ...
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294 views

Geometries of methyl and silyl radicals

The $\ce{.CH3}$ radical is planar but the $\ce{.SiH3}$ radical is a trigonal pyramid. Why are they different? After all, $\ce{C}$ and $\ce{Si}$ are in the same group.
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494 views

Radical Computational Calculations [closed]

I am trying to calculate the total energies for a particular organic molecule that undergoes radical decomposition. I was able to calculate the neutral molecule with the exact results of a paper I ...
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Formation of radicals from C-H and C-C bonds

Why do radical mechanisms favor the homolytic dissociation of a $\ce{C-H}$ bond over a $\ce{C-C}$ bond? The $\ce{C-H}$ bond is stronger in magnitude (and it's also slightly polarized), so why would ...
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156 views

Why don't electrons pair up in an oxygen radical?

In an oxygen radical (produced by the break down of O3 for instance), there are 2 unpaired electrons in the outermost subshell which make the molecule unstable. Why don't these electrons pair up which ...
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Formation of azobenzene from nitrosobenzene and N-hydroxyaniline

I'm trying to create a reasonable reaction mechanism for the reaction of nitrosobenzene and N-hydroxyaniline, which happens as part of the reduction of nitrobenzene to azobenzene using magnesium as ...
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Why is the methyl radical planar?

Why is the methyl radical planar? The VSEPR theory would predict an angle between 120 and 109.5 degrees, while it is actually 120 degrees.
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Why is O2 a biradical?

$\ce{O2}$ has a double bond in its normal form. That is $\ce{O=O}$. There are no unpaired electrons in this case are there since there are 2 lone pairs on each oxygen. However 1 resonance structure ...
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What exactly does it mean for the reaction of superoxide with non-radicals to be spin-forbidden?

From Wikipedia: The reaction of superoxide with non-radicals is spin forbidden. In biological systems, this means its main reactions are with itself (dismutation) or with another biological ...
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What is the functional difference between a radical anion and a nucleophile?

Radical Anions are hundreds if not thousands of times more reactive than nucleophiles (right?). A radical anion is just a molecule with an unpaired electron. Where as a normal radical is missing an ...
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169 views

Redox properties of methyl radical

The methyl radical, $\ce{.CH3}$, is a strong oxidant and a strong reductant according to Wikipedia. Why is this so? Any additional reasons to the ones below? I know that an oxidant itself is ...
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3k views

Why are radicals unstable?

Why are unpaired electrons especially reactive? Does pairing electrons decrease the reactivity of the electrons? But then doesn't forcing two electrons into the same orbital cost energy?

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