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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Stability of carbenes
For predicting the order of formation of carbenes from the following compounds (CHI3, CHBr3, CHF3), we can take a look at the stability of the halide anion that is formed (I- vs. Br- vs. F-) and the ...
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Major product of reaction between 1,1-dibromo-2-(pent-4-en-1-yl)cyclopropane and methyllithium
What is the major product of the reaction between 1,1-dibromo-2-(pent-4-en-1-yl)cyclopropane and methyllithium in diethyl ether?
I suppose the nucleophilic double bond will react with the ...
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It is possible to synthesize 3,3-diethylpentane ("tetraethylmethane") from carbon tetrachloride?
Compounds like tetraethyl silane or tetraethyltin can be made from their tetrachlorides using ethylating Grignards, but what about substituting carbon, would it work or steric hindrance would prevent ...
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What role does CaCl2 play in a gelation medium?
To produce sodium alginate beads coated with chitosan, following procedure was undertaken:
Sodium alginate was dissolved in distilled water at a concentration of 4% (...) The gelation medium was ...
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Why does the Wurtz-Fittig reaction occur?
In the Wurtz-Fittig reaction, an aryl halide and an alkyl halide react with sodium in the presence of dry ether to give R-Ar as the major product. Why is the coupling of R and Ar favoured? In other ...
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Why doesn't sodium form organometallic compounds with alkyl halides?
Both magnesium as well as lithium, on reaction with an alkyl halide (say chloroethane), form an organometallic compound. However, sodium and potassium do not exhibit such a reaction. Instead of ...
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What does phosphorodibromidous acid do in solution?
When tribromophosphine is used to activate an OH to enable its substitution, the leaving group is listed by PubChem as "phosphorodibromidous acid" and doesn't seem to really exist from a ...
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Selection of parent chain in a halogenated compound with double and triple bonds
We were asked to select the parent chain for naming the halogenated compound containing double and triple bonds:
My teacher told me that we choose the orange (1) one over the blue one (3) because as ...
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If LiF is ionic in nature, why can't it dissolve in water?
LiF is prominently ionic compound. I also know polar substances can be dissolved in water as "like dissolves like". Why is then LiF only weakly soluble, in comparison with LiCl, or LiBr, ...
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Explaination of order of leaving groups
In Solomons' Organic Chemistry, in a section discussing leaving groups, it is stated that$-$
Among the halogens, an iodide ion is the best leaving group and a fluoride ion is
the poorest:
$$I− > ...
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Would fluorides stabilize zirconia?
The reason for zirconia's cubic and tetragonal phases not being stable is that the cation-anion ratio is too small for proper contact between ions.
One way is to use other oxides that have a bigger ...
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1-Bromo-4-tert-butylbenzene reaction with NaNH2 [closed]
I'm struggling to grasp how the reaction would turn out. Could you help?
My idea was that the bromide atom will get replaced by the amino group of $\ce{NaNH2}$, but when I google, I read that $\ce{...
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With two reagents common on Mars, fluorite and CO2, how would I produce carbon tetrafluoride?
The hypothetical terraforming of Mars would require the heating of the atmosphere. A commonly suggested method is the in-situ production of fluorocarbons, powerful greenhouse gases.
For example, ...
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How to produce AgI nanoplates?
I'm trying to understand the procedure used to produce AgI nanoplates described in the linked paper. Specifically, I have a few questions about the following text:
When silver acetate is in ...
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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 ...
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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 ...
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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.
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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 ...
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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 ...
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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 ...
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Constituents of LaI2 [closed]
An ionic solid $\ce{LaI2}$ shows electrical conduction due to presence of which anions and cations?
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Why doesn’t the reaction between 3-mercaptopropionic acid and methyl iodide yield a methyl ester? [closed]
Problem
Answer
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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 ...
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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 ...
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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 ...
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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 ...
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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 ...
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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 ...
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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 ...
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Thermal instability of sulfur and selenium iodides
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 ...
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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$...
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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 ...
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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?
$$\...
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+M or -I for chlorine? Major product in free radical chlorination and bromination of 2-chloropropane?
Is the +M or -I effect more dominant in when an alkyl (mono)halide is subject to free radical chlorination/bromination?
For example what will be the major product in case of free radical (mono)...
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Haloalkanes gives acid base reactions or SN2
Consider the following reaction:
I am confused whether $SN_2$ reaction will take place or acid - base reaction.
According to me:
This should be an acid - base reaction since the carbonanion(On carbon ...
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Why does potassium bifluoride exist whereas bichloride does not?
Why does the reaction \eqref{rxn:R1Q} take place, but the reaction \eqref{rxn:R2Q} does not?
$$
\begin{align}
\ce{HF(aq) + KF(aq) &-> KHF2(aq)}\label{rxn:R1Q}\tag{R1} \\
\ce{HCl(aq) + KCl(aq) &...
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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 ...
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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?
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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 ...
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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 ...
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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 ...
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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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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.
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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 ...
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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,...
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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....
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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 ...
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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 ...
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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 ...
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