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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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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Percentage yeilds of the reaction between tert butyl bromide and silver nitrite

I know that, $$ \ce{R-X + AgNO2 -> R-NO2 + AgX} $$ I have been taught that here nitro alkanes are major than nitrite esters and I have also been taught that this reaction proceeds through SN1 ...
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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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2 answers
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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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4 votes
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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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2 answers
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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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1 answer
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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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2 answers
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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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Electrophilic addition when both phenyl group and alkene is present [duplicate]

Actually my doubt is that why the answer is C? I proceeded through markonikov addition, Carbocation formed on 2nd Carbon from benzene ring, did a rearrangement as the carbocation gains stability due ...
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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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Double bond or carbanion for nucleophillic attack [closed]

I came across this question: According to me the Hydride ion should take hydrogen from left (unsubstituted carbon) because carbanion will be more stable there and this carbanion will then act as a ...
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Can there be a gas-phase electrolyte?

Reading the first paragraph in Wikipedia's I found one sentence particularly interesting: Some gases, such as hydrogen chloride ($\ce{HCl}$), under conditions of high temperature or low pressure can ...
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2 answers
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Can a Grignard reagent form magnesium halide with an alkyl halide? [duplicate]

$$\ce{RMgX + R'X' -> RR' + MgXX'}$$ Is this reaction possible? I am not able find any reference to it in the books that I have. Anyone has a reference?
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Why does HCl act as a weak base in HF solvent, even though it is a stronger acid compared to HF?

I've read that $\ce{HCl}$ acts as a weak base in $\ce{HF}$ solvent, which means $\ce{HCl}$ is supposed to lose $\ce{H+}$ ion to $\ce{HF}$. $\ce{HF}$ is a weak acid compared to $\ce{HCl}$, then shouldn'...
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What is the IUPAC name for this compound containing a phenyl group attached to it?

What is the IUPAC name for the compound $\ce{(CH3)3CCH2CH(Br)C6H5}$? The answer I got myself was (1-Bromo-3,3-dimethylbutyl)benzene, but from looking online most sources list the name as 1-Bromo-3,3-...
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How is 3-bromocyclohexene converted to cyclohexane?

My attempt is illustrated below: or Which of these methods is most viable?
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SN1 reaction of alkyl halides

I was going through Peter Sykes organic chemistry where I came across a section where the author is saying: For halides that do not readily undergo SN1 attack ,this can be promoted by use of silver ...
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Does ammonolysis of primary and secondary alkyl halides proceed through SN2 mechanism?

We know that the first the ammonia acting as nucleophile attack the alkyl halide forming the substituted ammonium salt, but my question is why cannot it proceed through a typical $S_\text N2$ type, ...
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6 votes
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Analysing reaction with chair conformation of substituted cyclohexane

Why doesn't Iodine liberate in the following reaction? (A) Inadequate ring size (B) Two Bromines are in equatorial positions (C) Steric hindrance of t-butyl group towards attacking $\ce{I-}$ ...
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bromobenzene and NaOH reaction at high temperature and pressure

Find the product of the following reaction Note that the carbon marked as a star is a special labelled carbon which may be considered as a $\ce{C-14}$ isotope The given answer is (c) Why would the ...
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2 votes
2 answers
215 views

Is regioselectivity affected by steric factors during alkylation of naphthalene?

I read that Friedel Craft's alkylation of naphthalene by alkyl halides having more than 2 carbons occurs at 2-position. On the other hand, with smaller halides, it occurs at the 1-position. Does it ...
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4 votes
2 answers
319 views

What is the major product in the reaction between 4-chloropentanal and lithium aluminium hydride?

What would be the major product between 4-chloropentanal and $\ce{LiAlH4}$? After the reduction of the aldehyde, would the hydroxyl group formed at $\ce{C-1}$ attack $\ce{C-4}$ causing cyclization to ...
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3 votes
0 answers
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Why is NaCl so abundant in the ocean [closed]

Why is sodium chloride far and away the most abundant salt dissolved in ocean water. Its two constituent ions do have a very high frequency in the crust of the earth but they are far from the most ...
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2 votes
1 answer
136 views

Why is it technically inaccurate to say that the decrease in reactivity of halogens is due to decreasing electronegativity?

I came across the following information in this post. Below the infographic there is a paragraph with a disclaimer: As another disclaimer, the reactivity of the halogens decreasing down the group ...
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9 votes
1 answer
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What is the IUPAC name of perchloroisobutane?

What is the IUPAC name of $\ce{(CCl3)3CCl}?$ The answer I got was 1,1,1,2,3,3,3-heptachloro-2-(trichloromethyl)propane. But when I looked up the question online, most sources say the answer is 2-(...
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5 votes
2 answers
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Why is acylation giving the major product compared to alkylation in the reaction between benzene and chloroacetyl chloride?

Why are we getting this products as major and the other as minor ? According to my knowledge, the carbocation formed on the $\alpha$-carbon of the carbonyl chloride is more stable than the ...
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2 votes
1 answer
319 views

Can aqua regia/royal water dissolve lead? [duplicate]

As known aqua regia can't dissolve $\ce{Ag}$ because formation of $\ce{AgCl}$ precipitate. Similarly will aqua regia precipitate $\ce{Pb}$ as $\ce{PbCl2}$? OR It is not possible to observe this ...
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How are 3 center-4 electron bonds any different from 2 center-2 electron bonds? [closed]

How are the bridge bonds in $\ce{Al2Cl6}$ different from the terminal bonds? We could have just mentioned the bridge bond formed by $\ce{Cl}$ as a coordinate bond. Why introduce this extra concept? I ...
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3 votes
1 answer
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Siiloxane polymer experiment

I believe the first reaction would be a substitution of $\ce{SiMe3}$ for $\ce{I}$ and creating $\ce{SiMe3Cl}$. The second process I think would involve the $\ce{Mg}$ removing the two $\ce{Cl}$ and ...
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2 votes
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Does Copper(I) Iodide have a dimer?

A qualitative test for the iodide ion involves reacting the salt solution with copper sulphate. This is said to yield the triiodide ion and the white precipitate of $\ce{Cu2I2}$. I haven't been able ...
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8 votes
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(E)-2-bromo-1,4-difluoro-3-iodobut-2-ene or (E)-3-bromo-1,4-difluoro-2-iodobut-2-ene

I am struggling with naming this structure either (E)-2-bromo-1,4-difluoro-3-iodobut-2-ene or (E)-3-bromo-1,4-difluoro-2-iodobut-2-ene. I am aiming at the question whether there is also a ...
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-4 votes
1 answer
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Can bromo(chloro)fluoro(iodo)methane be synthesized? [closed]

Bromo(chloro)fluoro(iodo)methane is supposed to have all of the stable halogens a part of this molecule: fluorine, chlorine, bromine, and iodine. Can it really able to be synthesized and if so could ...
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6 votes
1 answer
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The reaction of Alkyl Halides with sodium nitrite in DMF

How does the reaction of Alkyl Halides with sodium nitrite in DMF proceed? I was aware of the reaction of alkyl halides with aqueous sodium nitrite which results in the formation of an alkyl nitrite ...
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9 votes
1 answer
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Can fluorine ever have a positive oxidation state?

I know fluorine is the most electronegative element but can we humans ever synthesize fluorine in a positive oxidation state like +1?
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2 votes
1 answer
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What is the difference between an Aryl Halide and a Vinyl Halide?

Are aryl halides a type of vinyl halide? From my knowledge, when a Halogen atom is directly bonded to a doubly bonded carbon atom it is a Vinyl halide. When we look at halogen atom directly bonded to ...
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3 votes
1 answer
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Determining the mechanism followed when alcohols undergo a reaction with sodium bromide and sulphuric acid

$$\ce{R-OH + NaBr + H2SO4 -> R-Br + NaHSO4 + H2O}$$ Due to sulphuric acid, the $\ce{-OH}$ group will get protonated and convert into $\ce{-H2O+}$ which is a great leaving group in comparison to the ...
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4 votes
1 answer
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Yield of alkyl chloride in the Hunsdiecker reaction

Apparently the yield of alkyl chlorides is low as compared to that of alkyl bromides when preparing alkyl halides using the Hunsdiecker reaction. Why does this occur? The only factor I can see is the ...
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3 votes
1 answer
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Products of the reaction between ethoxyethene and HI

Problem The products formed in the reaction $$\ce{CH2=CHOCH2CH3 + HI ->}$$ are (a) $\ce{CH2=CHI}$ and $\ce{CH3CH2I}$ (b) $\ce{CH2=CHI}$ and $\ce{CH3CH2OH}$ (c) $\ce{CH3CHO}$ and $\ce{CH3CH2I}$ (d) ...
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Does optical isomerism fall under the category of stereoisomerism?

I have been asked to find the total number of dichlorination products (including stereoisomers) for the following reaction: I have figured out nine possible structures out of which two are optically ...
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Solubility of Beryllium Compounds in Water [duplicate]

Why is $\ce{BeF2}$ is highly soluble in water but $\ce{Be(OH)2}$ is insoluble? Both release $\ce{Be^{2+}}$ ion so this means they both have high hydration enthalpies and can easily overcome their ...
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