Questions tagged [halides]

Chemical compounds that contain halogens (group 17 in the Periodic Table) as part of their chemical structure. This tag should only be applied where the halide group is one of the main focuses of the question.

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Solubility of CsCl

I was just learning in analytical chemistry about classical cation separation and in the $\ce{HCl}$ group I was wondering why $\ce{CsCl}$ is apparently easily soluble in water when $\ce{AgCl}$ ...
Selenimoon's user avatar
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Strength of Hydrohalic Acids [duplicate]

Considering three molecules $\ce{HF, HBr, HI}$ - I want to compare acidic strength of them (theoretically) $\ce{H-F}$ bond has the highest polarity so I thought this polarity would lead F to take the ...
Himalayan's user avatar
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What is the enthalpy change for elimination reactions of alkyl halide - exothermic or endothermic?

There are a few questions in thermodynamics (with unverified data) that the addition reaction of ethene to give ethyl chloride has a +ve enthalpy change, thereby elimination to give alkene must be ...
Che Mistry's user avatar
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Why is the melting point of meta-diiodobenzene higher than that of ortho-diiodobenzene?

I'm currently trying to reason for as why the melting point of meta-diiodobenzene higher than that of ortho-diiodobenzene and I'm unsure of what to say. I understand the para isomer has the highest ...
bigmannus's user avatar
-6 votes
1 answer
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Formation of carbocation on reaction with strong acid in presence of halogen [closed]

Shouldn't the carbocation be formed away from the -I effect of the Cl atom for more stability. Backbonding is achieved in a later step after hydride shift.
Meet Shah'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
2 votes
2 answers
155 views

Does ferrocenium chloride ([Fe(C5H5)2]Cl) exist as a stable compound?

I am interested in using ferrocenium chloride ($\ce{[Fe(C5H5)2]Cl}$) for a synthesis application, but I couldn't find any sources referring to its existence, even though some websites and a figure in ...
psansoldo's user avatar
6 votes
1 answer
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Whatever happened to the use of perfluoroalkanes as breathable liquids or blood substitutes?

Some liquid perfluoroalkanes have very high solubilities and carrying capacities for gases like oxygen and carbon dioxide. In the 1980s and 1990s there were experiments showing that animals could &...
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What is meant by 'as Cl2'

I feel like I'm over thinking this one, but think I need a confirmation (and quantified example) to put my confusion to bed. I'm more a mechanical than chemical background but trying my best. I really ...
Kuhrta's user avatar
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Constituents of LaI2 [closed]

An ionic solid $\ce{LaI2}$ shows electrical conduction due to presence of which anions and cations?
WATCHER's user avatar
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Why doesn’t the reaction between 3-mercaptopropionic acid and methyl iodide yield a methyl ester? [closed]

Problem Answer Question I don’t understand why 3‐methylthiopropionic acid (X) is the correct answer. Wouldn’t sulfur and carbon have similar electronegativities? As the consequence, isn’t it more ...
nmrislife's user avatar
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Solubility of fluoroalkanes [duplicate]

I know haloalkanes generally aren't soluble in water due to their inability to form hydrogen bonds in water, despite being moderately polar. I was wondering why this is the case with fluoroalkanes too ...
Baishnavi Prasad's user avatar
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Weight Ratio vs Molar Ratio - Chloramines

I'm working with a delicate experiment whilst trying to test corrosion of stainless-steels in a chloramine environment. I've run into various literature that discusses the formation of different types ...
Kuhrta's user avatar
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Chloramines & Nitrogen Trichloride vs Stainless Steel [closed]

We've recently experienced excessive corrosion on stainless steel within indoor pool environments. We believe this is due to chloramine (gasses) in the atmosphere. To test this, I plan to create a ...
Kuhrta's user avatar
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Substitution or elimination when a chloroalkene reacts with NaOH in ethanol?

NaOH + EtOH will eliminate the Cl atom forming a double bond. At least, that's what I think. 3 could also be a viable answer since the OH can also attack the said double bond (this is probably not ...
Aranya's user avatar
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Why 2-methyl-1-propene's halohydrin formation does not involve steric effect?

This concerns Marc Loudon's Organic Chemistry 6th Edition's 5.2 page 187. Consider 2-methyl-1-propene and its halohydrin formation mechanism. Usually, there will be formation of bromonium, where I ...
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How to distinguish silver chloride, bromide and iodide?

When we test for chloride, bromide and iodide ions we use the obvious silver nitrate and dilute nitric acid test. However distinguishing between the precipitates is often quite tricky. How can we tell ...
Goffried Leibniz'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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Weakness of S−I and Se−I bonds

After recent question about non-existent pnictide(V) iodides, I stumbled upon a similar issue in oxygen group. For example, $\ce{SI2}$ was reported to be found… but at the temperature as low as $\pu{9 ...
Mithoron's user avatar
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How much can we extend the Finkelstein reaction?

Finkelstein reaction explicitly entails the conversion of an alkyl chloride or alkyl bromide to alkyl iodide by treatment with sodium iodide in acetone. $$\ce{R−X + NaI→[acetone] R−I + NaX↓ }\\ \ce{(X$...
D13G's user avatar
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Does resonance stablization of carbocation increase ease of $\ce{S_N1}$ reaction or decrease it due to delocalization?

(A) (B) In both of the cases when a nucleophile approaches for $\ce{S_N1}$ reaction a carbocation is formed in place of $\ce{Cl}$ atom. I know that the rate of $\ce{S_N1}$ increases with increase in ...
AltercatingCurrent's user avatar
5 votes
1 answer
571 views

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
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+M or -I for chlorine? Major product in free radical chlorination and bromination of 2-chloropropane?

Is the +M or -I effect more dominant in when an alkyl (mono)halide is subject to free radical chlorination/bromination? For example what will be the major product in case of free radical (mono)...
Valoruz's user avatar
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Haloalkanes gives acid base reactions or SN2

Consider the following reaction: I am confused whether $SN_2$ reaction will take place or acid - base reaction. According to me: This should be an acid - base reaction since the carbonanion(On carbon ...
Shekhar Dangi's user avatar
9 votes
2 answers
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Why does potassium bifluoride exist whereas bichloride does not?

Why does the reaction \eqref{rxn:R1Q} take place, but the reaction \eqref{rxn:R2Q} does not? $$ \begin{align} \ce{HF(aq) + KF(aq) &-> KHF2(aq)}\label{rxn:R1Q}\tag{R1} \\ \ce{HCl(aq) + KCl(aq) &...
I.Bedi's user avatar
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Why is the boiling point of a iodoalkane greater than that of the corresponding fluoroalkane?

Why is the boiling point of ethyl iodide (b.p. 72 °C) higher than the boiling point of ethyl fluoride (b.p. −37 °C) even though the dipole–dipole interaction should be better in $\ce{C2H5F}?$ Is it ...
advait singh's user avatar
-1 votes
1 answer
470 views

reaction of PCl5 with alcohol [closed]

I am able to think of two possible mechanisms for alcohol+PCl5 here, SN1 and SN2. In SN1, Inversion won't occur whereas, in SN2 inversion will occur. Which of the two is correct?
NNG's user avatar
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How does KI catalyze the reaction with H2O2?

I've done a Google search regarding this question, and have found that there is no place online which answers this question to the degree that I want. Unfortunately, every site online stops at the ...
Mwoodrg's user avatar
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5 votes
1 answer
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Mechanism for a reaction of reduced fluorophenol with BF3?

In the given question, $\ce{BF3}$ will act as an electrophile. Will it form $\ce{BF4-}$ and leave a positive charge on the carbocation to which $\ce F$ was attached or react with $\ce{OH}$. It will ...
Vansh Bhardwaj's user avatar
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0 answers
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Dehalogenation of vicinial halides via Sodium Amide vs Sodium Ethoxide [duplicate]

I noticed that vicinial dihalides can undergo elimination to create two alkenes or an alkyne. These are the following reactions I've seen. From Solomons & Fryhle 10th Edition Organic Chemistry ...
chemN00b's user avatar
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3 votes
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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 ...
user73910's user avatar
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1 answer
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Why are iodine precipitates yellow? [closed]

Why do iodine precipitates appear yellow? Learning about precipitates I noticed that compounds like Lead Iodide and Silver Iodide are yellow.
hanning's user avatar
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2 votes
1 answer
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Why is Hg2Cl2 less soluble in water than HgCl2?

I learned that $\ce{Hg2Cl2}$ is almost insoluble to hot water and $\ce{NH3}$ water in my textbook, but $\ce{HgCl2}$ dissolves well in water. I wanted to know the reason and searched for it. It's ...
satoru kurita's user avatar
-1 votes
1 answer
286 views

Which Group 16 elements form stable dihalides?

My textbook says that "except oxygen, all elements of group 16 form dichlorides and dibromides", while other sources quote that only Oxygen and Sulphur form dihalides and dibromides. Whereas,...
Chem1234's user avatar
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Why can't RX add to alkenes / alkynes like HX?

With an analogous mechanism: C bonded to X has a δ+ charge and attacks the pi electrons to form a carbocation intermediate, with X- as a leaving group. X- then adds to the carbocation to neutralize it....
kvanderfluegh's user avatar
9 votes
1 answer
923 views

How does xenon react with O₂F₂?

This reaction was asked in my college entrance exam. I searched through the entire Internet, but I couldn't find any papers/sources. I suspect since O₂F₂ is a strong fluorinating agent, one of the ...
Ayush Kumar's user avatar
16 votes
1 answer
2k views

Has anyone sysnthesized perfluorocubane (AKA octafluorocubane)?

Up until now, there have been attempts at synthesizing octafluorocubane, shown below, but success has been elusive. Has there been any success, and how might the symmetry and fluorine's electron ...
DrMoishe Pippik's user avatar
6 votes
1 answer
223 views

Lithium hydride from lithium fluoride

There is a method of preparation of LiH by reacting a lithium halide (chloride, bromide, or iodide) with sodium hydride in an inert organic diluent such as tetrahydrofuran. Is it possible to replace a ...
wolfRAMM's user avatar
2 votes
0 answers
59 views

Why bromoacetone is more reactive towards SN2 than alkyl bromides? [duplicate]

Compare the rates towards SN2 reaction: I got the point that 2-bromobutane d is a secondary halide, so the steric hinderance is highest making it least reactive among the four. Both b and c are ...
Arpit Raj Choudhary's user avatar
5 votes
1 answer
369 views

Why does the 1H NMR spectrum of methacryloyl chloride show two singlets instead of two doublets for vinyl protons?

Based on what I have understood, for methacryloyl chloride there is a geminal coupling of the vinyl protons since they are not chemically equivalent. Why are two singlets observed for vinyl protons ...
Elnani's user avatar
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5 votes
1 answer
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What would be the product(s) when 2-iodobutane is heated with tertiary butoxide?

The following question from Black Book Organic Chemistry IIT JEE Advanced Level Papers [1]: Choose the correct option(s) among the following about [P]: A) Two C−H bonds in [P] are involved in ...
Ayush Shankaram's user avatar
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Why isn't formyl chloride stable? [duplicate]

I am currently studying methods of synthesising ketones and aldehydes and one of the methods is Friedel-Crafts acylation. However, my teacher told our class that we can't use this to make benzaldehyde ...
math and physics forever's user avatar
1 vote
1 answer
409 views

Does the 3D structure generated with MolView violate the wedge-dash rules of "above/below the plane"?

I've been taught that in a wedge-dash diagram, the wedge represents a bond above the plane of the paper, and the dash represents a bond below the plane. Accordingly, I expected the structure of this ...
Righter's user avatar
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4 votes
1 answer
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Has tellurium(II) iodide been properly characterized ever?

According to Wikipedia, tellurium tetraiodide decomposes on heating: $$\ce{TeI4 ->[\Delta] TeI2 + I2}$$ However, the reaction is somewhat wrong as according to this 2008 paper: Solid tellurium ...
Nilay Ghosh's user avatar
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Why is methane not called carbon tetrahydride?

If aluminium hydride, $\ce{AlH3}$, is called "hydride" because it contains elemental hydrogen and sodium chloride, $\ce{NaCl}$, is called "chloride", and calcium carbide $\ce{CaC2}$...
ielnahhal's user avatar
1 vote
0 answers
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Chlorinated hydrocarbon destruction

What's a convenient method for lab-scale destruction of chlorinated hydrocarbons? Reductive dechlorination, total oxidation are fine as well as other routes you want to point out. If specific ...
Lorenzo Lami's user avatar
4 votes
0 answers
202 views

Comparing stability of halide ions

I have to compare stability of halide ions : $\ce{F-},\ce{Cl-},\ce{Br-},\ce{I-}$ I am confused between two factors : As we go down the group , the size of given species increases which spreads the ...
Acc2's user avatar
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3 votes
1 answer
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Does red phosphorus with hydriodic acid reduce all alkyl halides?

$\ce{HI/P}$ is used for reduction of alcohols, aldehydes, ketones and acids to alkanes. As for alkyl halides, I have read that only alkyl iodides are reduced, whereas other alkyl halides do not: $$\ce{...
Ayush Shankaram's user avatar
1 vote
2 answers
1k views

Does hydrogen peroxide remove chloramine from water?

I know that a small amount of hydrogen peroxide will convert chlorine in drinking water into table salt, oxygen, and water: $$\ce{NaOCl + H2O2 → NaCl + H2O + O2}$$ What I can't find is what effect it ...
Ray Butterworth's user avatar
2 votes
0 answers
50 views

Why do silver halide crystals in suspension, develop a surface charge

This is a question related to analog photography. Photographic films have a suspension of silver halide crystals in them, and these crystals have adsorptive properties which are used in this ...
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