Questions tagged [halogenation]

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

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1answer
62 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 ...
3
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2answers
54 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: $\ce{Cl2->2Cl^. \quad(1) initiation}$ ...
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2answers
73 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?
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1answer
102 views

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 $\ce{H}$...
-1
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1answer
129 views

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 ...
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1answer
66 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 ...
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0answers
23 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: ...
0
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1answer
96 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 ...
0
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1answer
214 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 ...
2
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1answer
260 views

Di-alpha-halogenation of ketones in acidic medium

I was studying alpha-halogenation of ketones from LibreTexts Chemistry, Under acidic conditions the reaction occurs through the formation of an enol which then reacts with the halogen${^1}$. 1) ...
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0answers
144 views

Does acetophenone show haloform reaction?

Although acetophenone is a methyl ketone, as it is aromatic, it is immiscible in H2O so the last step in the haloform reaction should not occur? I couldn't find any source regarding the haloform ...
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0answers
72 views

Pyridinium Tribromide and Acetic acid

When brominating trans-stilbene with pyridinium tribromide, acetic acid is required. What purpose does acetic acid serve in the reaction? Shouldn't the tribromide be sufficient?
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1answer
1k views

What happens when HCl is added to acetylene in presence of mercuric ions?

Normal addition of Hydrochloric Acid to acetylene would give me a 1,1 Dichloro product. But I read that in presence of mercuric ions only one molecule of HCl is added to give Vinyl Chloride. Why does ...
1
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1answer
205 views

Reaction between phenylamine and halogens

I understand that phenylamine is considerably more reactive than benzene, meaning that it is able to react with bromine water to give 2,3,6-tribromophenylamine. But I was then wondering why I haven't ...
3
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3answers
599 views

Mechanism with hypohalite in haloform reaction

The haloform reaction is usually done in a solution of NaOH and $\ce{I2}$ (or indeed, any halogen). Now the first part of the reaction mechanism in the wikipedia page and in the most organic books ...
4
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2answers
88 views

Finding major product when bromonium compound is acted upon by a nucleophile

The original question is:- The major product obtained in the following conversion is:- (Note that Me here means methyl group) The initial step would be the formation of a bromonium ...
1
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1answer
884 views

Which will be the major monochlorination product? [closed]

Which of these compounds represents the major monochlorination isomer formed in the following reaction? According to selectivity theory, the answer should be (c). However, the given answer is (...
4
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1answer
2k views

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

Recently, we were learning about free radical halogenation in school. A set of notes given to us wrote that the rate-determining step is the propagation step. This seems to go against my understanding ...
2
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1answer
396 views

Bromination with NBS on cyclic structures

I found this question and the answer as shown in my book. I didn't understand why the bromine particularly entered the position shown in the answer. First of all, if a free radical was generated ...
7
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1answer
2k views

Why is free radical chlorination exothermic whereas bromination is endothermic?

In the energy profile diagrams below, it can be clearly seen that the free radical chlorination of an alkane $$\ce{RH + Cl2 -> RCl + HCl}$$ is exothermic. However, the corresponding bromination $...
4
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1answer
193 views

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

$\ce{FeBr3}$ catalyzes bromination and $\ce{AlCl3}$ chlorination. I'd like to know whether bromination and chlorination can be done in sequence without changing the catalyst? So - will using the $\ce{...
5
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1answer
3k views

Products of radical bromination and mechanism

My organic chemistry final is next Tuesday, and I have worked through the practice final. The last question is the following: Give and name all the compounds resulting from the radical monobromination ...