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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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
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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Why is CH2Cl2 called as methylene dichloride and not methylidene dichloride, as it's a geminal dihalide? [duplicate]
Our book, mentions that geminal dihalides, are those having 2 halides on same carbon atom, and their common name is alkylidene halides.
In that case, CH2Cl2 has 2 chlorides on same carbon atom, ...
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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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Formation of a 3c4e bond in Be2Cl4 [duplicate]
Can someone explain in simplified term what is happening in this “bridge bonding” between Be2Cl4 starting from BeCl2?
From my understanding, The Be in BeCl2 have an incomplete octet and is unstable, ...
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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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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 ...
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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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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 ...
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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 ...
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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 ...
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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 ...
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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 ...
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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}$$
However, the reaction is somewhat wrong as according to this 2008 paper:
Solid tellurium ...
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Why is methane not called carbon tetrahydride?
If aluminium hydride, $\ce{AlH3}$, is called "hydride" because it contains elemental hydrogen and sodium chloride, $\ce{NaCl}$, is called "chloride", and calcium carbide $\ce{CaC2}$...
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Chlorinated hydrocarbon destruction
What's a convenient method for lab-scale destruction of chlorinated hydrocarbons?
Reductive dechlorination, total oxidation are fine as well as other routes you want to point out. If specific ...
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Comparing stability of halide ions
I have to compare stability of halide ions : $\ce{F-},\ce{Cl-},\ce{Br-},\ce{I-}$
I am confused between two factors : As we go down the group , the size of given species increases which spreads the ...
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Does red phosphorus with hydriodic acid reduce all alkyl halides?
$\ce{HI/P}$ is used for reduction of alcohols, aldehydes, ketones and acids to alkanes. As for alkyl halides, I have read that only alkyl iodides are reduced, whereas other alkyl halides do not:
$$\ce{...
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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 ...
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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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Why do active methylene compounds give Sn2 reactions?
I dont understand why they are strong nucleophiles when the negative charge is resonance stabilised. Also it is bulky, is there any chance of elimination?
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What is the meaning of a “halide component” for Friedel–Crafts reaction? [closed]
Among the given halides, which one can be used as halide component for Friedel–Crafts reaction?
(a) Isopropyl chloride
(b) Bromobenzene
(c) Chlorobenzene
(d) Chloroethene
I don't understand what a &...
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major product formed in wurtz reaction in the given molecule[ 1,3-dibromo-2,2-di(1-bromomethyl)propane ]
This is the reactant molecule which undergoes wurtz reaction. All possible products are-
What will be the most favorable in all of these? In my opinion that the last one should not be the one because ...
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Identifying an alkyl bromide from NMR information
This question appeared on an exam and I translate it into English.
In the NMR $\ce{H^1}$ spectrum of a pure substance, with molecular formula $\ce{C4H8Br2}$, the following chemical shifts (in ppm) ...
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Why isn't there hydrofluoric acid in fluoridated water? [closed]
From what I've read, when water is fluoridated it's done so either by $\ce{NaF}$ artificially or $\ce{CaF2}$ naturally. If this is correct, shouldn't the reaction $\ce{CaF2 + H2O -> CaO + 2HF}$ ...
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Numbering of carbon chain in 3-bromo-2-methylpropene
I have a specific confusion in numbering the carbon chain for 3-bromo-2-methylpropene.
I found two carbon chains of equivalent length (three atoms) and equivalent side chains (one atom).
For both ...
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Substitution in aryl halides
I need to propose a route for the synthesis of 2-(bromomethyl)benzonitrile from 1-bromo-2-(bromomethyl)benzene. In the attached figure, the structure of the starting compound and the species to be ...
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Reaction of aqueous KOH and alcoholic KOH with alkyl halide [duplicate]
CONTEXT:
Here's reaction of alkyl halide with aqueous $\ce{KOH}$
and here's the reaction for dehydrohalogenation by alcoholic $\ce{KOH}$
Question
Initially $\ce{KOH}$ is aqueous. On reacting with ...
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Lithium Air vs Li Fluoride battery capacity [closed]
Lithium air aka lithium oxygen batteries are described as highest theoretical capacity battery possible. In wikipedia, it says lithium air has energy density 5210 Watt hour per kg, including weight of ...
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Why do different products form when alkali halide reacts with zinc in polar protic and aprotic solvents?
Let's take an alkali halide such as $\ce{CH3CH2Cl}$ the two reactions in polar protic and aprotic solvents are as follows:
$$
\begin{align}
\ce{CH3CH2Cl &->[Zn, CH3OH] CH3CH3}\tag{R1} \\
\ce{...
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