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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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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 ...
Vera Maria's user avatar
8 votes
2 answers
855 views

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 ...
Nightwing's user avatar
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10 votes
2 answers
607 views

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 ...
Nightwing's user avatar
  • 408
3 votes
2 answers
76 views

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 ...
trerri's user avatar
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1 vote
0 answers
48 views

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 ...
Darshit Sharma's user avatar
-1 votes
3 answers
113 views

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, ...
Maths lover's user avatar
0 votes
0 answers
40 views

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− > ...
Eisenstein's user avatar
2 votes
0 answers
65 views

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 ...
user145034's user avatar
1 vote
1 answer
111 views

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{...
wengen's user avatar
  • 423
4 votes
0 answers
96 views

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, ...
Galerita's user avatar
  • 141
1 vote
0 answers
40 views

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 ...
rmueller's user avatar
0 votes
0 answers
71 views

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
1 vote
0 answers
82 views

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
48 views

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
1 vote
0 answers
40 views

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
226 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
109 views

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 &...
matt_black's user avatar
0 votes
2 answers
193 views

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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-3 votes
1 answer
122 views

Constituents of LaI2 [closed]

An ionic solid $\ce{LaI2}$ shows electrical conduction due to presence of which anions and cations?
WATCHER's user avatar
1 vote
1 answer
119 views

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
0 votes
0 answers
32 views

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
0 votes
0 answers
631 views

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
  • 65
2 votes
0 answers
141 views

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
  • 65
1 vote
1 answer
414 views

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
  • 13
0 votes
0 answers
36 views

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 ...
user45765's user avatar
  • 101
6 votes
4 answers
2k views

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
208 views

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
  • 41
6 votes
1 answer
389 views

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 ...
Mithoron's user avatar
  • 4,580
-2 votes
2 answers
406 views

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
  • 89
-2 votes
1 answer
237 views

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
635 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
-3 votes
1 answer
113 views

+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
  • 89
0 votes
0 answers
63 views

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
2k views

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
  • 101
1 vote
1 answer
670 views

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
566 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
  • 1
1 vote
1 answer
1k views

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
  • 11
5 votes
1 answer
442 views

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
0 votes
0 answers
30 views

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
  • 342
3 votes
0 answers
67 views

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
  • 1,264
-2 votes
1 answer
373 views

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
  • 17
2 votes
1 answer
747 views

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
425 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
0 votes
0 answers
54 views

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
1k 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
234 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
60 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
409 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
  • 83
5 votes
1 answer
458 views

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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