Questions tagged [halogenation]

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

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Fluoride in water leading to black lung in miners [on hold]

I was wondering if the reaction of flouride from drinking water with carbon in the coal causes black lung disease, because the resulting carbon fluorine bond is a strong bond, and thus hard to ...
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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: ...
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63 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 ...
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1answer
55 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 ...
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1answer
112 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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62 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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29 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
435 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 ...
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1answer
70 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 ...
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1answer
181 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 ...
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67 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 ...
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1answer
364 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 (...
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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 ...
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1answer
272 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 ...
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1answer
1k 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 $...
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145 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{...
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1answer
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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 ...