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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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-1
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1answer
523 views

In Finkelstein reaction, how does precipitate formation favor forward reaction? [duplicate]

In my textbook it's stated that: $\ce{NaCl}$ and $\ce{NaBr}$ thus formed is precipitated in dry acetone. It facilitates the forward reaction according to Le Chatelier's principle. Is this related ...
2
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1answer
268 views

Can a first degree carbocation form if a methyl shift is possible?

I was going through a reference book when I stumbled upon this question Is that even possible?
4
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1answer
1k views

Elimination of tertiary alkyl halide with lithium aluminium hydride to give alkenes

I'm confused about the mechanism and thus cannot decide which alkene would be the product. Reaction with primary and secondary alkyl halides gives alkanes. What about this case?
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1answer
137 views

In halogenation of ethene using bromine for example, why does the lone pair of bromine attack the C atom?

In the presence of the electron rich (pi bond) of ethene, the bromine molecule becomes a temporary induced dipole, one end being electron deficient and acting as the electrophile. (The pi bond in) ...
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1answer
115 views

Percentage of yield reaction question

By bubbling $\ce{Cl2}$ in a solution containing $176.6~\mathrm{g}$ of $\ce{MgBr2}$ are obtained [sic!] $135~\mathrm{g}$ of $\ce{Br2}$. However, the yield of this reaction is not $100~\%$. How many ...
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0answers
462 views

Comparing acidity of p-chloro benzoic acid and p-fluoro benzoic acid [duplicate]

I am really confused about comparing the acidity of p-chloro benzoic acid and p-fluoro benzoic acid. The question here doesn't have a conclusion and the discussion here is confusing. My Try: -F and ...
3
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2answers
12k views

What is hybridisation of XeF6 in solid state?

According to the following formula: Type of hybridisation/steric no. = (no. of sigma bonds + no. of lone pairs) it should be $\ce{sp^3d^3}$, however according to my textbook it is $\ce{sp^3d^2}$ in ...
10
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1answer
572 views

Geometry of the pentachloridoindate(III) anion

According to Brown et al.,1 the crystal structure of $\ce{[NEt4]2[InCl5]}$ reveals that the pentachloridoindate(III) anion, $\ce{[InCl5]^2-}$, adopts a square pyramidal $C_\mathrm{4v}$ geometry (VSEPR ...
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1answer
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How to rationalise the planar structre of I2Cl6?

$\ce{I2Cl6}$ is a dimer of $\ce{ICl3}$. $\ce{ICl3}$ is T-shaped, with $\ce{I}$ being $\mathrm{sp^3d}$ and having two lone pairs. I read in Inorganic Reaction Mechanisms by R. K. Sharma that $\ce{...
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2answers
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Does fluorine ever form a double or triple bond?

Does fluorine ever form a double or triple bond? I wonder if seeming lack of such higher order bonds is related to the electronegativity of fluorine.
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594 views

Why is the silver nitrate chemical test more favorable than that of sodium iodide?

Two tests to determine the presence of alkyl chlorides are the silver nitrate in 1% ethanol and sodium iodide in 15% acetone tests. These two tests both produce a precipitate when added to chloride ...
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1answer
2k views

Why is CH2Br2 more polar than CH3I? [closed]

According to my textbook (A Level Chemistry a for OCR Student Book, Pages 84-5) $\ce{CH2Br2}$ is more polar than $\ce{CH3I}$. The molecules are both polar, they both contain different bonded atoms, ...
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2answers
1k views

Is there a haloalkane for astatine?

I'm studying organic chemistry, and I noticed that there are fluoro-, chloro-, bromo-, and iodoalkanes. However, there are none for Astatine. Could someone shed some light on this, and what it would ...
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3answers
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How to bleach polyester [closed]

I have a challenge. I recently bought a cotton/polyester coat with the intention of bleaching it to near-white. To my surprise, normal bleach with sodium hypochlorite had very little effect. It ...
3
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1answer
128 views

How does the use of inert gas in fluorination of saturated aliphatic hydrocarbons make it less violent?

While studying alkanes, I found this written in my book: Fluoridation can be achieved without violence when alkane is treated with fluorine diluted with an inert gas, or by the action of inorganic ...
2
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1answer
1k views

Simultaneous solubility of CaF2 and SrF2

Solubility of two electrolytes having common ion when they are dissolved in solution is called simultaneous solubility. How do I calculate the simultaneous solubility of the above mentioned salts ...
2
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1answer
1k views

Comparison of Resonance Energies of some Carbocations

We were given the following carbocations and asked to compare their resonance energies. $\ce{L-CH2+}$, where $\ce{L}$ is: $\ce{NH2}$ $\ce{OCH3}$ $\ce{Ph}$ $\ce{F}$ $\ce{Cl}$ $\ce{NO2}$ and the ...
2
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1answer
749 views

What is the major side product of the reaction between 2-bromo-2-methylpropane and hydroxide ion?

I know that one of the products will be 2-methylpropan-2-ol, arising via a $\mathrm{S_N1}$ reaction. But what else is formed? Specifically, I am looking for a side product that is gaseous.
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1answer
301 views

How do you tell whether fluorine goes to axial or equatorial position in iodine dioxide difluoride?

I need to find the $\ce{F-I-F}$ bond angle of $\ce{[IO2F2]^-}$. But the thing is I can put 2 fluorines in the equatorial or axial positions so I get 3 different answers. I'm guessing they're all ...
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0answers
102 views

Halogens and Equilibrium

Suppose 1 mol of $\ce{KI (aq)}$ is mixed with $\pu{1 mol}$ of $\ce{I_2^*}$, where $\ce{I_2^*}$ represents a di-iodine molecule which has been radioactively labelled, and the substances are allowed to ...
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1answer
2k views

What happens when a solution of sodium chlorite is acidified?

I'm told that when sodium chlorite $\ce{(NaClO2)}$ is mixed with aqueous acid, chlorine dioxide ($\ce{ClO2}$) is produced and remains mostly dissolved in water. I would like to know how the strength ...
3
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1answer
1k views

Are there stronger oxidizing agents than fluorine gas?

Are there stronger oxidizing agents than fluorine gas, so it could oxidize fluoride to fluorine? Also, in case of oxygen, fluorine gas can oxidize oxygen gas to the exotic dioxygenyl ion. Can ...
7
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1answer
434 views

Mechanism for bromoetherification of olefinic alcohol

Propose a mechanism for the following reaction showing the relevant stereochemistry of intermediates and the final product. I am confused as to what is going on here. I guess there's some sort ...
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1answer
582 views

Safest Methylating Agent

I am planning on doing some synthesis in the near future and due to safety purposes I am looking for a methylating agent that is both effective and safe. The substrate is a deprotonated amine and the ...
3
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0answers
253 views

Mechanism for conversion of gem-dihalide to carbonyl compound

How does nucleophilic substitution work in a compound consisting of two leaving groups? I understand that hydroxide ions will attack the carbon centre (which bears a partial positive charge) and ...
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221 views

Why do many organic halogen compounds smell or taste sweet?

Is it just coincidence that many organic halogen compounds (especially chlorinated ones) tend to either taste or smell sweet? Examples include dichloromethane, vinyl chloride, chloroform, and ...
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0answers
794 views

Is benzyl chloride or allyl chloride more reactive?

What compound is more reactive, benzyl chloride [(chloromethyl)benzene] or allyl chloride (3-chloroprop-1-ene)? I know that both have a higher reactivity than alkyl and aryl chlorides.
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2answers
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Why does cyclopropane react with bromine?

In my exam, I was asked why cyclopropane could decolourise bromine water (indicating that it reacted with the bromine). All I could guess was that it is related to the high angle strain in ...
16
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2answers
1k views

Gauche effect and bond length

Which of the following compounds has the longest bond length? (A) $\ce{H3C-CF3}$ (B) $\ce{FCH2-CH2F}$ (C) $\ce{F2CH-CHF2}$ (D) $\ce{F3C-CF3}$ My logic was based on the relative ...
11
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1answer
864 views

Friedel–Crafts alkylation of benzene with tetrachloromethane

There was this question in an exam at our school which asked what the major product will be when excess of benzene is reacted with tetrachloromethane in the presence of aluminium chloride. All of us ...
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1answer
5k views

Why doesn't NF₃ undergo hydrolysis?

I was reading Jan's answer to the following question-: Why can NCl3 be hydrolyzed but CCl4 cannot? Since nitrogen is less electronegative than fluorine, in NF3 the electrophilic site is the Nitrogen ...
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1answer
446 views

Why doesn't the N-Br bond dissociate quickly in NBS?

NBS is used to provide a constant, small amount of $\ce{Br2}$ which then dissociates to give $\ce{Br^.}$ free radical. Why doesn't the $\ce{N-Br}$ bond simply dissociate to give $\ce{Br}$? This ...
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1answer
1k views

Can the hydroxyl group of 4-hydroxybenzoic acid react with phosphorus pentachloride?

I learned that, a phenol will not react (or react very slowly) with $\ce{PCl5}$ due to its stabilized structure. How about the $\ce{-OH}$ group on the benzene ring of 4-hydroxybenzoic acid? Will that ...
3
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1answer
1k views

Order of citation of alkyl and halide prefixes in IUPAC names

I've been playing around with ChemDraw and found that it assigns the priorities of substituents in a way I wouldn't have expected, depending on the length of the alkyl substituent. I'm not a ...
27
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1answer
4k views

Why is fluorine a gas, but lithium isn't?

$\ce{F2}$ is a gas, but pure lithium is a solid metal. Why is this? Lithium is much lighter, just 3 protons and 3.9 neutrons (average). Fluorine is much heaver, 9 protons and 10 neutrons.
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2answers
2k views

Why does fluorine act as a leaving group in organophosphates?

C-F bond is the strongest single bond in organic chemistry with a bond energy of $\ce{453 kJ\,mol^{-1}}$. And it is very difficult to break this bond and F does not act as a leaving group. However, ...
2
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1answer
653 views

Kinetic vs thermodynamic control of HBr to 1,3-Butadiene

The author claims that the transition state leading to the formation of the 1,2 product from the allylic carbocation is lower in energy since the carbon (which is attached to Br in the 1,2 product) is ...
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1answer
1k views

Taste same but why not LiCl a substitute for NaCl (common salt)?

A clinical paper from 1949 [1] observes the toxicity of LiCl, at very low concentrations. That just went over my head... Is toxicity the only reason to avoid LiCl as a substitute for NaCl (specially ...
3
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1answer
563 views

Why is methyl iodide more dense than ethyl iodide, even though the latter has more carbon atoms?

It is understood that more carbon atoms present in a hydrocarbon, the greater the density of the hydrocarbon. But then why does $\mathrm{CH_{3}I}$ have a greater density than $\mathrm{C_{2}H_{5}I}$?
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1answer
451 views

Nucleophilic Substitution Reactions help

Which halogenoalkane reacts fastest with sodium hydroxide? A. 1-iodobutane B. 1-chlorobutane C. 2-chloro-2-methylpropane D. 2-iodo-2-methylpropane Iodine has a larger radius, thus less ...
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0answers
129 views

What is the product of the reaction of 2-bromo-1-fluoro-4-nitrobenzene with sodium methanethiolate?

In the reaction depicted below shouldn't $\ce{Br}$ be replaced by $\ce{SCH3-}$ ion as $\ce{Br-}$ is a good leaving group and the $\ce{C-F}$ bond is quite strong due to back bonding of 2pπ-2pπ orbitals?...
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1answer
2k views

Order of basicity of halides [duplicate]

The order of basicity of halides is $\ce{F- >Cl- > Br- > I-}$ My teacher explained this on the basis that the smaller is the ion, the greater is the charge/size ratio, hence it more ...
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1answer
470 views

Does chlorine in tap water usually contain traces of cornstarch (or its derivatives)? [closed]

My online research has been challenging to separate out the corn starch or corn Derivatives that are obviously in chlorine weather in tap water or pools. There is medical support backing it but I ...
3
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2answers
532 views

How would the “-COOCl” functional group be named?

I had this question that has been bouncing around for over 2 years. Basically, I imagined this molecule: This molecule, as far as my former (and current) knowledge of nomenclature goes, couldn't be ...
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2answers
6k views

Why do alkyl bromides and iodides develop colour when exposed to light?

My book says alkyl halides are colourless when pure. However, bromides and iodides develop colour when exposed to light. Why do they develop colour when exposed to light? It is important to note that ...
15
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5answers
7k views

Can fluorine act as the central atom in interhalogen compounds?

Why can't fluorine be the central atom in inter-halogen compounds? A $\ce{F-F}$ bond is weaker than a $\ce{F-X}$ bond and thus, fluorine should be happy to form inter-halogen compounds. But, why ...
0
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2answers
741 views

Between 3-chlorophenol and 3-fluorophenol, which one is more acidic?

Between 3-chlorophenol and 3-fluorophenol, which one is more acidic? In this case, I know that both F and Cl are electron-donating groups. Furthermore, I know that F is more electron-donating than ...
3
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1answer
3k views

Does SiCl2 exist and its possible structure

It's known that the elements in IVA all have valence +2 and +4. I also know there exists $\ce{GeCl2}$ and $\ce{SnCl2}$. So my question is does $\ce{SiCl2}$, or even $\ce{CCl2}$ exist? If yes, what ...
4
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1answer
293 views

Selenium oxydichloride bond angle

According to me , the $\ce{Cl—Se—Cl}$ bond angle should be greater than $\ce{Cl —Se—O}$ bond angle because since oxygen is more electronegative than $\ce{Cl}$ , the orbital directed towards $\ce{O}$ ...
5
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1answer
3k views

What is the hybridization of chlorine in vinyl chloride?

Is chlorine in vinyl chloride sp2 or sp3 hybridized? Calculating using steric number it is found to be sp3 hybridized. But according to I. L. Finar* it is sp2. *I.L. Finar: Organic chemistry Vol.1 ...