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Questions tagged [halogenation]

For reactions involving the formation of a C-X bond.

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Ratio of amounts of different mono substituted alkanes (by halogenation)

My problem here is the I'm unable to use the information for reactivity of C-H bonds to calculate the amount of mono chlorides. If anyone can help me in the process, that would be great.
Heisenberg 's user avatar
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Will benzyl halides undergo SN1 or SN2 mechanism in a polar aprotic solvent?

If benzyl bromide reacts with KF in the presence of a polar aprotic solvent like DMF, will it undergo SN1 mechanism or SN2 mechanism ? I understand that polar aprotic solvents favour SN2 mechanism but ...
standardsolution's user avatar
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Can I make orthophosphoric acid from sodium dihydrogen phosphate and an acid which I can use to make ethyl iodide?

For my project I needed to di-substitute benzamide with ethyl group at N position to create DEB as a mosquito repellent. The first part of creating benzamide I was able to do, but the second part of ...
N N-DiEthyl Benzamide's user avatar
3 votes
1 answer
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Free-radical addition of bromine to alkene

If light and radical initiators are present, radical addition of $\ce{HBr}$ to alkenes takes place and outcompetes electrophilic addition of $\ce{HBr}$ to alkenes. Why isn't a similar thing same ...
Silenus's user avatar
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Why does silver have more affinity for chlorine and bromine rather than fluorine in Swarts reaction?

Why do silver and other metals used in Swarts reaction $(\ce{AgF},$ $\ce{HgF2},$ $\ce{CoF2},$ $\ce{SbF3})$ have more affinity for chlorine and bromine even though fluorine is more electronegative? $$\...
barath kumar basker rangareddy's user avatar
3 votes
2 answers
384 views

Chlorination of 2-phenylbutane [closed]

When the compound is chlorinated on the extreme carbons, there is a chiral carbon in both the resulting compounds, which gives a total of 4 stereo isomers. When compound is chlorinated on 2nd or 3rd ...
Manthan Kale's user avatar
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How to find the percentage of chloroderivatives after monochlorination of a compound

There are series of examples in my textbook to decipher the chlorination selectivity. The example was to find percentage of monohlorderviatives of n-pentane after free radical halogenation giving ...
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Halogenation of organic acid derivatives

Chloropicrin can be produced through the reaction of sodium hypochlorite with nitromethane. On the surface, this seems to me to proceed through a mechanism analogous to the haloform reaction, with one ...
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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?

There's this problem that I saw in my Organic Chemistry book: The reaction between $\ce{(CH3)3CH}$ and $\ce{Cl2}$ forms two products: $\ce{(CH3)2CHCH2Cl}$ (63%) and $\ce{(CH3)3CCl}$ (37%). Why is the ...
blair's user avatar
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What is the major product in the following reaction?

Reaction: My thought-process: According to me, this reaction is like the bromination of alkene but here instead of $\ce{CCl4}$ solvent, we have $\ce{H2O}$ as a solvent. For the first step a $3$-...
Soumil Gupta's user avatar
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Kharasch Peroxide effect with heating

From what i have learnt, kharasch Peroxide effect is only applicable for HBr. The reason for this is for the other halogens, HCl and HI the propagation steps in the radical mechanism are endothermic. ...
Sage of Seven Paths's user avatar
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Why does Fluorine react differently than other halogens during Hydrohalogenation/Halogenation and also substitution with Alkanes?

From what I understand, during halogenation with an alkene or alkyne, diatomic gaseous halogen molecules can effectively 'break' the pi bond to produce a haloalkane/haloalkene. However I discovered ...
physicsphil's user avatar
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1 answer
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Why do radical inhibitors inhibit a reaction by creating a "more stable" radical, but for monohalogenation, we WANT to form the most stable radical?

According to my notes, radical inhibitors tend to turn a more reactive radical into a less reactive radical by making it more stable. For instance, the hydroquinone reacts with a radical species, ...
BlueMagic1923's user avatar
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What is the major product of the reaction between 1‐methylcyclohex‐1‐ene and BrCl? [closed]

Would the bromine add to the more substituted carbon due to selectivity?
THISISME's user avatar
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Product of reaction between cyclohexene and bromine in methanol at 273 K

What product could we expect when we let cyclohexene react with an equivalent of bromine in methanol at 0 °C? Is it just the trans-addition of bromine (rac.) or also the SN1-susbtitution on a carbon ...
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Why is carbon tetrachloride more stable than methane?

When a mixture of methane and chlorine is exposed to ultraviolet light – typically sunlight – a substitution reaction occurs and the organic product is chloromethane. However, the reaction doesn't ...
Invisible's user avatar
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Why aren't both alpha-carbons halogenated when acetone reacts with chlorine under UV?

My book shows the following reaction: Why is only one alpha carbon halogenated? I googled, but couldn’t find anything on it.
Tahsin Choudhury's user avatar
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Number of products formed in radical chlorination on a chiral center

If an organic compound with a chiral center of a specific (R) or (S) configuration, is chlorinated on that carbon center through a radical mechanism, will one product be formed or two? Basically will ...
Ashish's user avatar
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7 votes
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Possibility of further chlorination of hexachlorocyclohexane

The reaction of benzene with excess of chlorine in the presence of sunlight produces 1,2,3,4,5,6-hexachlorocyclohexane as the major product. This is also given in the preparation section of the ...
TRC's user avatar
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Why is chlorosulfite a good leaving group?

I came across the following website article[1]: I understand the mechanism and also get the fact that this is nothing but an experimental result but why does the $\ce{ClSOO-}$ group departs ...
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Bond Polarity vs bond length's effect on reactivity of haloalkanes

My textbook says: Carbon acquires partial positive charge whereas halogen acquires partial negative charge. Halogen becomes nucleophilic in character, which can be replaced by another nucleophile on ...
Shozab Lilani's user avatar
3 votes
2 answers
610 views

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

I am supposed to perform the above shown reaction in the lab soon, but I don't really understand the mechanism behind it. I got told by my lab assistant that the mechanism is an electrophilic aromatic ...
Anni.Lin's user avatar
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What happens when tran-2-butene reacts with aqueous bromine in the presence of chloride?

$\ce{Br2-H2O}$, containing some $\ce{NaCl,AlCl3}$ ? I initially though that there would be anti addition of Br and OH to give 3-Bromobutan-2-ol but then I also got the intuition that NaCl might ...
Prajwal Tiwari's user avatar
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Does the chlorination of 4-methylcyclopentene generate two enantiomers or two diastereomers?

Does the chlorination of 4-methylcyclopentene generate two enantiomers or two diastereomers? I think it makes two enantiomers (or one pair of enantiomer) since the starting compound is achiral, but ...
Yan Qin's user avatar
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What would be the major products of this reaction?

Obviously, A would be 3-Bromoo 3-methyl cyclo hexene: as the stable free radical intermediate would be formed. But B is what I am having problems with. I read that $\ce{LiAlH4}$ forms alkenes with ...
Prajwal Tiwari's user avatar
0 votes
1 answer
137 views

Is the polarisation of halogens of higher atomic number easier because the electrons are further away from its core?

This question concerns the dihalo addition reactions. I've learned that a halogen molecule (which, of course, consists of two atoms of the respective halogen) is more easily polarised by the double ...
AlgebraicsAnonymous's user avatar
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333 views

Exception to haloform reaction

While explaining haloform reaction my teacher told me that Me3C-(C=O)-CH3 does not give haloform reaction. What is the reason behind it since it does have a CH3 group?
Singularity's user avatar
1 vote
1 answer
204 views

Halogenation by Phosphorous tribromide vs using HBr

My textbook introduced $\ce{PBr3}$ by stating that it leads to an inversion in stereochemistry since it always goes through an SN2 pathway, unlike using $\ce{HBr}$. My question is that since $\ce{Br-}$...
Tsz's user avatar
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Halogens chemical reactions with each other [closed]

https://en.wikipedia.org/wiki/Halogen Can Halogens react with each other? Examples : Chlorine + Flourine Flourine + Iodine Iodine + Bromine Chlorine + Bromine and so on. Permutations and Combinations. ...
Prashant Akerkar's user avatar
3 votes
0 answers
273 views

What makes a good chlorinating agent?

From what I know, good inorganic chlorinating agents, $\ce{SOCl2, PCl3, PCl5}$ are able to substitute a poorer leaving group (like $\ce{OH-}$) for chlorine. For example, for substitution of the ...
chematwork's user avatar
5 votes
1 answer
1k views

Safest way to conduct a reaction with bromine under reflux conditions

I am conducting an electrophilic aromatic bromination reaction according to literature. The substrate and intended substitution pattern do not matter, but the reported procedure requires the dropwise ...
Jan's user avatar
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1 vote
1 answer
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sp2 hybridisation of alkyl radicals causing formation of racemic mixture

What I know about $\ce{^{.}CR3}$ radical is that it has both $\ce{sp^2}$ and $\ce{sp^3}$ character but the $\ce{sp^2}$ character dominates and so the radical is $\ce{sp^2}$ in nature. So, suppose we ...
user avatar
1 vote
0 answers
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Problem encountered during high school unsaturated fats experiment

To get straight to the point, my chemistry experiment was looking at the amount of unsaturated fats in avocado oil with respect to temperature. I did this by testing for the $\ce{C=O}$ bonds using ...
K King's user avatar
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2 votes
0 answers
307 views

why the terminal Br/Cl is an electrophile in AlBr5/AlCl5 complex? [closed]

In halogenation of benzene, e.g. bromination, $\ce{AlBr3}$ and $\ce{Br2}$ is added in order to make $\ce{Br+}$ by forming delivery agent $\ce{AlBr5}$ (step 2 of picture). Why is the terminal (...
234ff's user avatar
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3 votes
1 answer
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Total number of isomers formed on monobromination of 2-methylbutane

What is the total number of isomers formed on monobromination of 2-methylbutane (including configurational and stereoisomers)? I tried working it out. However, I found only five: According to the ...
Vamsi Krishna's user avatar
1 vote
1 answer
80 views

Why 4‐methylidenespiro[2.4]heptane cannot be converted to 1‐chlorobicyclo[3.2.0]heptane? [closed]

According to the solution, the following reaction is not correct: But why? I have tried solving in the following steps: Forming a carbocation by breaking the double bond. Expanding the ring. ...
Manu Shukla's user avatar
2 votes
0 answers
113 views

Where will halogenation take place?

In the following halogenation reaction: At which position will halogenation take place? It is obvious that the halogenation will take place at a 3° Carbon atom (the rates of halogenation for ...
Aniruddha Deb's user avatar
1 vote
1 answer
443 views

Reaction Mechanisms: Free Radical Halogenation

In Free Radical halogenation using chlorine and sunlight, why does the chlorine-free radical get attached to the allylic carbon? Will it be correct to say that it follows the anti-Markovnikov rule? ...
Devaesh's user avatar
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-2 votes
1 answer
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Can iodine replace other halogen as well?

While reading about halogen family I encountered the reaction: $$\ce{NaClO3 + I2 -> NaIO3 + Cl2}$$ I know that that the oxidizing tendency of halogens decreases down the group, so I think that the ...
user89505's user avatar
1 vote
2 answers
1k views

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? [duplicate]

In free radical substitution of propane with a halogen (eg- chlorine), how do you know which carbon out of the three ends up with an unpaired electron after fission of C-H bond? This image shows ...
XXb8's user avatar
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-1 votes
2 answers
124 views

Does halogen addition occur without sunlight [closed]

Can this reaction occur; (2-Bromopentane) + Br2 --(300°C)--> (2,3-Dibromopentane) As far as I know, halogenation can only occur in UV or sunlight, not with just a high temperature. So how does this ...
harry's user avatar
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2 votes
1 answer
140 views

Reaction of octahydroazecine with iodine crystals [closed]

I really don’t understand why the following reaction would take place first of all. So this is a sub part of a question wherein we have to compare the basicity of the compounds formed through some ...
Muskaan's user avatar
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3 votes
2 answers
1k views

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

I am trying to derive the overall rate equation for the photocatalysed halogenation (chlorination) of an alkane that proceed via this 4 step chain reaction: $\ce{Cl2->2Cl^. \quad(1) initiation}$ $\...
S R Maiti's user avatar
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5 votes
2 answers
223 views

Halogenation of 4‐methylcyclohex‐1‐ene

My problem is with the methyl group. If it wasn't there, I had no problem. When the halonium bridge is made does the methyl group shift to give a more stable transition state or not?
Amir's user avatar
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1 answer
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What is the mechanism for trans-stilbene to stilbene dibromide?

What is the mechanism for trans-stilbene to stilbene dibromide? This is what I know: The bond between the hydrogen and bromine is broken and the bromine is given a negative charge, while the $\ce{H}$...
mk2025's user avatar
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1 answer
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Can sulfuric acid attack a hydrocarbon/paraffin? Under what conditions? [closed]

Sulfuric acid can attack benzene and other hydrocarbons (when mixed with hydrogen peroxide). Also, chlorine gas and bromine can replace hydrogen(s) in hydrocarbons like methane, ethane, propane,butane ...
Aryan Gupta's user avatar
1 vote
1 answer
743 views

Bromination of an alkene in presence of water

Bromination of an alkene in presence of water results in its mechanism in a cyclic bromonium ion and "afterwards $\ce{H2O}$ binds to the carbon atom surrounded by more electron donating groups." This ...
user208973's user avatar
1 vote
0 answers
54 views

Will a Lewis acid catalyze the reaction of HBr with primary alcohols?

It is well-established that a Lewis acid catalyst (popularly $\ce{ZnCl2})$ is necessary to form an alkyl chloride when reacting $\ce{HCl}$ with a primary alcohol. This actually changes the mechanism: ...
David Reed's user avatar
0 votes
1 answer
415 views

Mechanism of 5‐(iodomethyl)oxolan‐2‐one synthesis from 4‐pentenoic acid and iodine in acetonitrile [closed]

There is a question in my organic chemistry textbook with an answer. What it doesn't explain (and neither does my theory textbook, I checked) is the mechanism involved in the reaction. The reaction is ...
Claudio Lancia's user avatar
1 vote
1 answer
3k views

How many products does this reaction yield?

How many products can we get from the monochlorination of 2,4-dimethylpentane including stereoisomerism? I have seen someone say that it yields 3 structural isomers one of which has two enantiomers ...
ALPHAz CoC's user avatar