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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5answers
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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 ...
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2answers
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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
390 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 $\ce{O}$ ...
6
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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 ...
6
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1answer
59 views

Effect of Base on E2 product

One base is bulkier than the other, that's my observation. How does it affect the product? Could someone please give proper reasoning and the product? Thanks a lot. P.S. I guess both follow E2
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1answer
494 views

Why is ammonium chloride rather than an alkylammonium chloride salt the product of nucleophilic substitution of a chloroalkane by ammonia?

My textbook said that when an excess of ethanolic ammonia is heated with a haloalkane ($\ce{R-X}$) one should give the products as being $\ce{R-NH2}$ and $\ce{NH4Cl}$ as opposed to $\ce{RNH3Cl}$. I ...
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1answer
2k views

Rules for benzene halogenation

Can anyone please show me the rule on how a halogen like bromine reacts with benzene, such as when bromine replaces hydrogen? I'm wondering what happens after the first hydrogen is replaced? Does it ...
4
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2answers
482 views

Is the 5d orbital involved in triiodide ion?

Is the $5\mathrm{d}$ orbital involved in the triiodide ion, $\ce{I3-}$? There are $5$ electron pairs around the central iodine. (Almost) all of the hypervalent compounds involve the most ...
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1answer
680 views

Chlorine Fluoride, why not Fluorine Chloride

Why is Chlorine Fluoride called "Chlorine Fluoride" rather than "Fluorine Chloride"? As I was taught in school that normally that when nonmetal combine with nonmetal then we write the compound with ...
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1answer
463 views

Displacement reactions of Halide ions

I understand that the reactivity decreases as you go down group 7. In displacement reactions the more reactive halide replaces the least reactive halide, but in this question i do not understand the ...
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1answer
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Why add acid to rid of soluble carbonate or hydroxide impurities? Will it not also react with halide I'm testing for

When identifying metal halides with silver ions, the positive ion $\ce{Ag+}$ will form $\ce{AgX}$ with halide in a solution. However, $\ce{H+}$ is added (typically in the form of an acid like $\ce{...
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1answer
747 views

Why does AsF3 boil at 60.4 Celsius and AsF5 at -52.8?

I don't understand why the boiling point of $\ce{AsF3}$ is at 60.4 degrees Celsius and $\ce{AsF5}$ boils at -52.8 degrees Celsius. I understand that it has to do with the bondings, but I can't see ...
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1answer
250 views

Why doesn't tetraiodine exist?

I've run into a question that says after doing the Lewis structure of $\ce{IF3}$, which I did, explain why $\ce{I4}$ doesn't exist. I am confused as to how it can be explained. I've thought that ...
11
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2answers
901 views

N-fluorosuccinimide: any scope?

All halogen derivatives (except fluorine) of succinimide exist and are used in various chemical processes. What makes N-fluorosuccinimde difficult to prepare? Still chemists have not been able to ...
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1answer
169 views

Why would this rearrangement happen?

So, I am a first year chemistry student and I saw this chemistry reaction on a previous year's test. I attempted to figure out the mechanism, but I'm rather confused as to how the cyclopentane somehow ...
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0answers
573 views

Why can the anion NO3- behave as a L-type ligand while BF3 can not? [closed]

The fluorine has a lone pair, and the oxygen has a lone pair. Both are donate-able, so they should both act as ligands. I know fluorine is more electronegative, but oxygen is quite electronegative ...
2
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1answer
986 views

Deciding the major product in this Wurtz reaction

Today I was told: When 2-chlorobutane is reacted with 2-chloropropane in the presence of sodium and dry ether the following products are formed: 2,3-dimethylpentane 3,4-dimethylhexane 2,3-...
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1answer
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Why does 2-chloropropane's mass spectrum have a peak at 27?

I have noticed that all halogenoalkanes of the form 2-Xpropane seem to have a mass spec peak at 27, implying that a $\ce{C2H3+}$ ion is being formed. Forming a $\ce{C2H3+}$ ion, however, would mean ...
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1answer
2k views

Why doesn't fluoride ion have highest nucleophilic power (nucleophilicity)?

As you can see from the image above, '$\ce{R3C}$' anion has 1 lone pair '$\ce{R2N}$' anion has 2 lone pairs $\ce{RO}$ anion has 3 lone pairs $\ce{F}$ anion has 4 lone pairs According to VSEPR theory,...
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2answers
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Why do XeO and XeF8 not exist?

Since Neil Bartlett's 1962 discovery that xenon was capable of forming chemical compounds, a large number of xenon compounds have been discovered and described. Almost all known xenon compounds ...
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1answer
602 views

What are the products in this reaction?

I came across this question I thought that the answer should be option (a)but the answer is given option (d) I thought that other products might be a result of the following mechanism But this ...
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1answer
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Trend in the boiling point of the hydrogen halides

The boiling points of the hydrogen halides are as follows: $$\begin{array}{cc} \hline \text{Species} & \text{Boiling point / }\mathrm{^\circ C} \\ \hline \ce{HCl} & -85.1 \\ \ce{HBr} & -...
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3answers
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Determining the product which is not possible in the reaction

This is an objective type question I encountered in a objective test. NBS (N-bromosuccinimide) is used for the allylic substitution of $\ce{Br}$ in a reaction. In this reaction, since the allylic ...
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1answer
590 views

What is the nucleophile in alkaline hydrolysis of a haloalkane?

We know that haloalkanes are able to undergo $\mathrm{S_N1}$ or $\mathrm{S_N2}$ in alkaline hydrolysis, and the hydroxide ion is the nucleophile responsible for attack. But when we talk about ...
4
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1answer
242 views

What does addition of iodine and base do this case?

I figured that the first reaction just adds a bromine to the meta position but I don't know what step ii) does. The only thing I can think of is the base gets rid of the alpha hydrogen next to the ...
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1answer
2k views

Mechanism of the reaction of an alkene with excess HI in presence of CCl4

This was the given alkene: I thought of Markovnikov's rule and wrote out what I thought the final product should look like based on it, but apparently that's wrong. I can't figure out the mechanism ...
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1answer
204 views

Oxide and chloride of a metal [closed]

I found this problem: The oxide of a metal contains 60.0% metal and the chloride of the same metal contains 25.26% metal (in mass percents). What are the possible formulas for the oxide and the ...
15
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1answer
713 views

Alphabetization rule in case of consecutively placed substituents

This is the compound: I am stuck on assigning the locants to the given halo substituents. We know that all halogens are of equal priority. So, using first point of difference, we get either an $\ce{I ...
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1answer
285 views

Redox reactions of halides in hexane

When we have two test tubes and we add: In the first test tube: hexane, aqueous solution of $\ce{NaCl}$ and aqueous solution of $\ce{I2}$ In the second test tube: hexane, aqueous solution of $\ce{...
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1answer
242 views

Reaction mechanisms for organohalides from alcohols

For the syntheses of organohalides from alcohols, what would plausible reaction mechanisms be for the three following reactions? $$ \ce{R-OH + NaBr + H2SO4 -> R-Br + NaHSO4 + H2O} $$ $$ \ce{R-OH +...
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1answer
420 views

Friedel-Crafts Alkylation and hybridization

Why must the alkyl halide be sp3 hybridized with respect to the carbon connected to the halogen for the alkylation to occur? Why, for example, can't we use acetylide with a bromine substituted for ...
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1answer
4k views

Why does water favour nucleophilic substitution over elimination?

The two broad ways a halogen can leave a haloalkane are nucleophilic substitution and elimination reactions. I was told that elimination reactions (that form a double bond as a $H^+$ is also removed) ...
7
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1answer
634 views

How can I dispose of chlorine and sodium hydroxide as table salt and water?

If I used chloralkali electrolysis of brine to produce hydrogen, and can't use the other products (or not all of them), what route(s) can I take to revert them back to brine? I figured, since I have ...
5
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2answers
618 views

Balancing complex haloform redox reaction

I just completed a haloform reaction experiment, using acetophenone and sodium hypochlorite to form benzoic acid and chloroform. My lab report has a question regarding balancing the equation of the ...
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1answer
730 views

Why isn't a polar protic solvent used in the Finkelstein reaction?

Usually, in a nucleophilic substitution reaction, a stronger nucleophile replaces a weaker nucleophile. In any polar protic solvent, the order of nucleophilicity is $\ce{F-}<\ce{Cl-}<\ce{Br-}&...
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1answer
551 views

How to determine the stereochemistry after elimination of anti-1-bromo-2-methylcyclohexane?

The question is asking for the product and the answer is C. My expected answer was E. Here's how I tried to solve it: Since Br (the leaving group) is at the equatorial position, the structure would '...
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1answer
454 views

Why does Fluorine have a high affinity for Calcium?

I keep hearing from several websites and videos that Fluorine seems to like bonding to Calcium specifically; can someone please tell me why? I can't seem to find a clear response on the internet. ...
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1answer
192 views

Indonesian Chemical Olympiad: Calculating mass from predicted reaction

This problem is taken from the Indonesian Chemical Olympiad. A sample containing barium peroxide was added to a glass full of sulfuric acid. It produced an insoluble product and its filtrate. The ...
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1answer
299 views

Preparation of a fluoride solution using CaF2

I need to prepare several solutions with different concentrations of $\ce{F-}$, in order to carry out some investigations on fluoridated water. Would this be achievable by dissolving calcium fluoride, ...
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1answer
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Titanium in HF vs HCl

So we tried the reaction between Titanium metal with hydrochloric acid and hydrofluoric acid at a similar concentration. While boiling temperatures and constant heat over a long period of time are ...
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1answer
2k views

Can chlorine form hydrogen bonds? [duplicate]

My question is simple, If chlorine ($\ce{_17Cl^35^.^5}$) and nitrogen ($\ce{_7N^14}$) have similar values of electronegativity, and chlorine has way more lone pairs than nitrogen, what prevents it ...
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1answer
2k views

Comparing the Lewis acidity of carbon tetrafluoride and silicon tetrafluoride

I've been asked to compare the relative acidity of $\ce{CF4}$ and $\ce{SiF4}$. As both atoms have noble gas configurations, neither can act as a lewis acid and so I assume the question is inferring ...
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1answer
2k views

Why are alkyl halides used as solvents for relatively non polar compounds and not polar compounds?

It is written in my textbook that : Alkyl halides are used as solvents for relatively non polar compounds. Alkyl halides are themselves polar with carbon having delta positive charge and halide ...
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1answer
910 views

Which affects acidity more, in relation to induction? (Distance vs. quantity)

I already know that the answer is III. I'm just looking for further explanation on how the others compare to each other, mainly IV vs V. I know that iodine is less electronegative than chlorine, ...
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1answer
166 views

Does mercury chloride (ii) evaporate at room temperature? [closed]

if you leave mercury chloride (ii) exposed to air in a room does it evaporate to any significant level which can cause toxicity?
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1answer
1k views

Oxidation state of Halogens

So the question is which is the most common oxidation state of halogens and I have to justify my answer. Is my following thought correct? Do I have to add something? The most common oxidation state ...
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1answer
86 views

Why are only elemental halogens used in oxidation of thiols?

I know that purpose of molecular halogen like $\ce{Br2, Cl2}$ is to take away extra electrons on sulfur so that sulfur bridge can form. But can you use any other molecule beside halogen to do the same ...
3
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0answers
51 views

Can iodine hydrocarbons be used as fire extinguishing agent? What are their properties?

In the German Wikipedia the following claim about fire extinguishing agents is made: Iodkohlenwasserstoffe haben zwar eine hervorragende Löschwirkung, erlangten wegen ihres exorbitant hohen ...
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0answers
108 views

Synthesis of para-chloroanisole using diazotisation followed by chlorination with aluminium chloride

Is this a legitimate reaction scheme to synthesise para-chloroanisole from benzene and methanol as the only organic reactants? $$\ce{C6H6 -> HNO3/H2SO4 -> H2/Pd -> HONO/{Ethanol}\\ -> {...

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