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Why do resorcinol and iodine react to give 2-iodobenzen-1,3-diol?

Reading this question, I realized that OP is very new to organic chemistry, and in need for learning a lot about electrophilic aromatic substitution reactions. Thus, I recommend that OP should ...
Mathew Mahindaratne's user avatar
8 votes
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The major product of radical halogenation: Why is it a halogen attached to a primary carbon and not a tertiary carbon in the given example?

The experimental relative rates of chlorination to primary, secondary, and tertiary positions are $1$, $3.8$, and $5$, respectively. In the given compound $\ce{(CH3)3CH}$, there are $9$ identical ...
Infinite's user avatar
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7 votes
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sp2 hybridisation of alkyl radicals causing formation of racemic mixture

In the first step, due to the selectivity of bromine in a free radical reaction, the tertiary carbon which has a $\ce{-CH3}$ group attached to it forms the radical. Now, since the radical is a $\ce{^{....
Safdar Faisal's user avatar
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Possibility of further chlorination of hexachlorocyclohexane

Given enough exposure time, the reaction will lead to formation of various products, even the fully chlorinated compound: dodecachlorocyclohexane. Increasing the concentration of chlorine also help in ...
Nilay Ghosh's user avatar
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6 votes
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Mechanism with hypohalite in haloform reaction

The mechanism of haloform reaction will also be almost similar in the case if we use hypohalites (here, it is $\ce{NaOCl}$). In the first step, instead of $\ce{OH-}$, the acidic $\alpha$ proton will ...
Soumik Das's user avatar
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6 votes
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Chlorination of 2-phenylbutane

First of all, welcome to ChemSE! I presume that you are a student, which I am not, and that this problem arises from a preparatory examination. Too many of these types of questions are ambiguous at ...
user55119's user avatar
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6 votes

Why does silver have more affinity for chlorine and bromine rather than fluorine in Swarts reaction?

Silver actually does prefer fluorine over heavier halogens. But this preference involves less (free) energy difference than the preference for the alkyl groups for fluorine. As a result, transfer of ...
Oscar Lanzi's user avatar
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5 votes
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Safest way to conduct a reaction with bromine under reflux conditions

Check if you may skip using elemental bromine as starting material altogether. An alternative approach may be running the bromination in a heterogenic, biphasic setup with the couple $\ce{NaBrO3/...
Buttonwood's user avatar
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5 votes
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Reaction of octahydroazecine with iodine crystals

Chlorination and bromination of alkenes are very general reactions, and mechanistic study of these reactions provides additional insight into electrophilic addition reactions of alkenes. Although much ...
Mathew Mahindaratne's user avatar
5 votes

What is the major product of the reaction between 1‐methylcyclohex‐1‐ene and BrCl?

This is not a radical process. $\ce{BrCl}$ is a source of $\ce{Br+},$ so this is the addition of $\ce{Br+}$ to the alkene followed by capture of the cation (bromonium ion) by $\ce{Cl-}$ [1]. The ...
Waylander's user avatar
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4 votes
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Bromination with NBS on cyclic structures

As a follow-up to the excellent comments provided thus far, the following thoughts are added. Electrostatic Potential Map of azulene (1a) shows that there is high electron density in the 5-membered ...
user55119's user avatar
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What is the major product in the following reaction?

Once you have the chloronium ion, you can think of it as having either of two carbocation structures, which are formed by breaking one or the other carbon-chlorine bond. Whichever carbocation is more ...
Oscar Lanzi's user avatar
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3 votes

Halogenation of 4‐methylcyclohex‐1‐ene

In order for a methyl shift to occur, there would need to be an empty orbital resulting from a carbocation intermediate for the methyl group to occupy. Note that in the bromonium intermediate shown ...
elucidium's user avatar
3 votes

How many products does this reaction yield?

The expected products of mono-chlorination of 2,4-dimethylpentane are depicted in following scheme: The substrate has 12 primary hydrogens (on 1-,1'-, 5-, and 5'-methyl groups), 2 secondary ...
Mathew Mahindaratne's user avatar
3 votes
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Bromination of an alkene in presence of water

While there is no formal carbocation intermediate, the cyclic bromonium intermediate has a few different resonance forms (reference): As you can see on the right, in the structure representing the ...
Greg D's user avatar
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3 votes

Does acetophenone show haloform reaction?

Fuson and Bull [Chem. Rev., 15, 275 (1934)] found acetophenone to give a positive iodoform test. They modified the usual procedure, adding dioxane as a cosolvent to better dissolve water-insoluble ...
Anger Density's user avatar
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Can bromine water be used to compare the reactivity of liquid 1-heptene and liquid heptane?

According to this Wikipedia article: "In electrophilic halogenation the addition of elemental bromine or chlorine to alkenes yields vicinal dibromo- and dichloroalkanes (1,2-dihalides or ...
airhuff's user avatar
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3 votes

Does the Lewis acid have to match the halogen in electrophilic halogenation of benzene

The reason you use the respective halides for halogenation is that the halogen and Lewis acid can inter-react to form a chemical equilibrium if you don't. $$\ce{FeBr3 + Cl2 <=> Cl+ + [FeBr3Cl]- ...
A.K.'s user avatar
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3 votes

What is the rate-determining step in free radical halogenation?

It does seem odd as a blanket statement. However, the bond dissociation energies (BDEs) for Cl2 and Br2 are quite low, 243 and 193 kJ/mol, respectively, while BDEs for the C-H bond in alkanes are much ...
Organic Chemistry Explained's user avatar
3 votes

Does the chlorination of 4-methylcyclopentene generate two enantiomers or two diastereomers?

For an anti addition, you get enantiomers (left two structures) in equal amounts. The enantiomers in the orientation shown are related by a mirror plane swapping left and right: For a syn addition, ...
Karsten's user avatar
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3 votes

Why do resorcinol and iodine react to give 2-iodobenzen-1,3-diol?

An electrophilic aromatic substitution reaction is one in which the aromatic ring reacts (as a nucleophile) with an electrophilic reagent. In all of the reactions that follow this naming convention, ...
Ben Norris's user avatar
3 votes

Why is carbon tetrachloride more stable than methane?

It is impossible to compare the stability of methane and carbon tetrachloride directly as the do not have a common frame of reference. At the same time you cannot claim that the dichlorine molecule is ...
Martin - マーチン's user avatar
3 votes
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Kharasch Peroxide effect with heating

If the reaction is endothermic, then it cannot be proceeded by just applying heat. $\ce{HCl}$ is a very stable acid with $\ce{H-Cl}$ much stronger than $\ce{H-Br}$ bond and hence not broken ...
Nilay Ghosh's user avatar
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2 votes
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Finding major product when bromonium compound is acted upon by a nucleophile

I'd like to point out that the ketone would actually disfavor an attack at its alpha position: Placing two positive charges on adjacent carbon atoms is much less favorable than not, especially when ...
ringo's user avatar
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2 votes

Reaction between phenylamine and halogens

Chlorination of aniline with chlorine is rapid and gives 2,4,6-trichloroaniline according to the references cited in this paper here. The earliest reference cited is 1845 by AW Hofmann so it has been ...
Waylander's user avatar
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2 votes

What is the mechanism for trans-stilbene to stilbene dibromide?

The key feature in the product that shows what is going on is the trans configuration of the two bromines. This is characteristic of the addition of elemental bromine via a brominium ion mechanism ...
Waylander's user avatar
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2 votes
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Can sulfuric acid attack a hydrocarbon/paraffin? Under what conditions?

TLDR: Sulfuric acid act as catalyst in the isomerization reaction of parafin hydrocarbons and sometimes it produce undesired sideproducts like sulfonate salts, napthenic acid, bisulfite ions etc. from ...
Nilay Ghosh's user avatar
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2 votes
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Total number of isomers formed on monobromination of 2-methylbutane

Here are the six structures that your source is probably referencing.
kskinnerx16's user avatar
2 votes

Deriving rate law from a reaction mechanism for a chain reaction using steady-state approximation

In the book that Wikipedia cites (Advanced Organic Chemistry: Reaction Mechanisms By Reinhard Bruckner, ISBN 9780080498805), they have a different set of assumptions. They are saying the formation of ...
Karsten's user avatar
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2 votes
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In free radical substitution of propane with halogens, how do you know which carbon ends up with an unpaired electron after fission of C-H bond?

This is to do with the relative stabilities of the free radicals produced. Here is a schematic diagram showing the two possibilities for propene (similar mechanism, also with two free radical ...
arevmelikyan's user avatar

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