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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Ring expansion in cyclo compounds

In the following reaction, why does ring expansion not take place? Mechanism that was the correct one: In the second step when there is a protonated carbon the ring should expand to become 6 ...
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Trichloride ion (c.f. triiodide ion)

While triiodide ion is commonly known, why is that trichloride ion (and its salts) almost unheard of? While it does exist according to literature, why is the stability of trichloride ion in aqueous ...
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Stability of F- Cl- Br- I-? In aqueous state [closed]

If we talk about hydrolysis F- will be more heavily hydrolysed so it should be more stable in aqueous state. But I know that HI is a stronger acid than HF. So the stability of conjugate acid ie I- ...
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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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What is the structural formula of alkali hypohalite: MOX or MXO?

There seems to be an inconsistency in the formula. Somewhere it is written as MOX and in some places, it is written as MXO. This is what Google gives when you search sodium hypochlorite: I think the ...
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Reaction of Alkyl Halide with Ag2S / Na2S

What does alkyl halides give on reaction with $\ce{Ag2S / Na2S}$? In my book, it is given as $\ce{R-S-R}$ but I am not quite sure as alkyl halide react with moist $\ce{Ag2O}$ to gives $\ce{R-OH}$ and ...
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Order of boiling point of group 14 halides

Find out the species having lowest boiling point: (A) $\ce{SnCl4}$ (B) $\ce{GeCl4}$ (C) $\ce{SiCl4}$ (D) $\ce{CCl4}$ I have considered the inert pair effect of $\ce{Sn}$ here which will make the ...
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Can Ethanol be used to carry out SN1 reaction?

My book says that the reaction of $$\ce{Cl-CH2-O-CH2-CH3}$$ with ethanol to form $$\ce{CH3-CH2-O-CH2-O-CH2-CH3}$$ occurs through $\mathrm{S_N1}$ mechanism, but shouldn't it actually be $\mathrm{S_N2}$...
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Reaction of an alkyl halide with silver nitrite

I want to know that whether both alkyl nitrite and nito alkane are produced or if nitroalkane is the only product. There are many different (contradicting) things written in different books that is ...
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Stability of CI4 and PbI4

I have read in my textbook that $\ce{CI4}$ is more stable than $\ce{PbI4}$ due to inert pair effect. But shouldn't we also consider the effect of steric repulsions? In $\ce{CI4}$, four large iodine ...
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Why benzenediazonium bromide and iodide are not important?

When we think of aryldiazonium compounds, the first compound that comes to mind is benzenediazonium chloride. Sure thing, the compound is versatile and has been used to make a vast array of organic ...
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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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Boron trihalides acidity

A boron trihalide ($\ce {BX3}$) is a Lewis acid, because it can accept an electron pair, as per Gilbert N. Lewis' definition. Now my question is- Arrange $\ce {BF3}$, $\ce {BCl3}$, $\ce {BBr3}$ ...
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Conversion of propane to methane [closed]

I had a question in my textbook to convert propane to methane. The basic idea was chlorination in presence of sunlight. However, two products are obtained in this case - namely 2-chloropropane and 1-...
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Darzens reaction on allylic position

Question Attempt I thought the products would be from simple darzens reaction. So I replaced the OH by Cl. But the answer of mine seems way wrong. Do give some tips on what might be happening in ...
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Which site would NaCN attacks (SN2)?

Question Attempt I thought that the bromine atom farther from the ring would be substituted because of less hindrance, but the book says opposite, why?
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Can Cyanide ion substitute methoxide? [closed]

Question Attempt Since CN is better nucleophile than both OMe and Cl, I believe that it should replace both. But none of the options match my answer. Where am I wrong? Please help.
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Comparing between nucleophilic and basic strength of acetylene ion [closed]

Question In this question I understand that 2 reactions- Substitution and elimination- will occur. But which will be major?
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847 views

Reaction between anisole and concentrated HI in excess

Question: My Attempt: In most of the ethers reaction of HI in excess yields alkane iodide products. But in case of anisole two scenarios are possible, I believe: The HI breaks bond between methyl ...
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Comparing between SN2 and E2

Question I am confused between the questions B. And C. The earlier is SN2 and later is E2. But what makes the difference?
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What is the effect of polar protic solvent on nucleophilicty? [closed]

Question Attempt: I could figure out the answer correctly using simple rules governing nucleophilicity . But my doubt is how does polar protic solvent affect nucleophicity. And what would be the ...
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What would the following NGP reaction yield?

Question Attempt I believe that in first reaction there would be simple Sn2. In the second reaction there Should be NGP. Hence i think the products should be diastereomers. But answer is (A)they are ...
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What kind of conjugation occurs in in intermediate formed during SN2 reaction of allylic system?

I had read about the good reactivity of allylic systems towards SN2s. In SN1 there is stabilisation of intermediate carbocation through resonance. What kind of conjugation occurs in SN2?
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Dipole moment difference between ch2f2 and ch3f [duplicate]

In CH3F and CH2F2 the net dipole moment increases from 1.82 to 1.97 while in all other halogen substituted carbon atoms the dipole moment decreases. In the case of CH3Cl and CH3F the chlorine ...
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When is a compound sterically hindered?

In a nucleophilic substitution reaction , which one of the following undergoes complete inversion of configuration ? (A) $\ce{C_6H_5CCH_3C_6H_5Br}$ (B) $\ce{C_6H_5CHCH_3Br}$ (C) $\ce{C_6H_5CHC_6H_5Br}$...
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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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Why is phosphorus trifluoride the strongest Lewis acid among the phosphorus trihalides?

I had read that for the trihalides of boron, boron trifluoride is the weakest Lewis acid due to backbonding. The order I had seen was - $\ce{BI3 > BBr3 > BCl3 > BF3}\$ $$\ce{}$ $- order of ...
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Why does treatment of a geminal dihalide with sodium amide lead to an alkyne and not an allene?

I've come across the following problem in Klein's Organic Chemistry, 2nd edition: However, I'm a little bit confused about why the terminal alkyne is produced. I believe that an allene should be ...
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Comparison of boiling points

I was comparing boiling points of $\ce{CHCl_3}$ and $\ce{CH_3Cl}$. According to me B.P. of $\ce{CHCl_3}$ should be higher due to it's higher molecular mass than $\ce{CH_3Cl}$, but the answer is ...
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Is HF the least acidic hydrogen halide?

Fluorine is the most electronegative halogen and therefore, there is larger difference in electronegativity between the atoms of $\ce{HF}$ than any other hydrogen halide, which means the positive ...
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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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Comparison of I-F, Br-F, and Cl-F bond strengths

From Chemistry of the Elements by Greenwood and Earnshaw [1, p. 833]: Figure 17.9 Mean bond energies of halogen fluorides. This shows the mean bond energy for $\ce{X-F}$, where $\ce{X}$ is a ...
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Lewis acidity comparison of boron and aluminium trichlorides

Lewis acidity is a function of electron deficiency on the acceptor atom, which in this case is $\ce{B}$ and $\ce{Al}$ respectively. Back donation is better as is the case of $\ce{B}$, due to better ...
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Are the reaction rates of these equations equal? [closed]

$$\ce{CH3CH2CH2Br + OH- -> CH3CH2CH2OH + Br-}$$ $$\mathrm{rate} = k[\ce{CH3CH2CH2Br}][\ce{OH-}]$$ If I change the $\ce{Br}$ with any element from halogens (without changing concentration, volume, ...
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Mechanism for Chromyl Chloride Formation

This is the very famous chromyl chloride test, used for detection of chloride ion in solution - $$\ce{K2Cr2O7 + 4NaCl + 6H2SO4 -> 2CrO2Cl2 + 2KHSO4 + 4NaHSO4 +3H2O}$$ When a mixture containing ...
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What product is formed in the Wurtz reaction of 1-bromo-3-chlorocyclobutane?

I want to do Wurtz reaction of 1-bromo-3-chlorocyclobutane: Wikipedia suggests to do an intramolecular reaction. Instead, I remember reading somewhere that bromine is more reactive and hence we ...
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Can a per-acetylated sugar anomerize?

So I have a question concerning a reaction mechanism for the reaction below. I know for certain that I get the alfa anomer, but I can't explain it. When I draw out the mechanism it doesn't make sense ...
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How do we predict the order of melting points of group 1 and group 2 halides?

I get really confused by this: The order of melting points of group 2 chlorides is: $$\ce{BaCl2 > SrCl2 > CaCl2 > MgCl2 > BeCl2}$$ This is completely understandable by Fajan's Rules. But,...
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Why London force dominates in Alkyl Halides

Why London Force is greater than dipole-dipole interactions in Alkyl Halides? As we know that most of the time London force is weaker than other forces. Then why in this case it's not so? ...
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Why is 1,2-diiodoethane unstable? [duplicate]

Diiodoethane is a product of the reaction between glycol and $\ce{PI3}$. Why is 1,2-diiodoethane unstable?
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Why does alcoholic KOH prefer elimination whereas aqueous KOH prefers substitution?

What is the basic difference between aqueous and alcoholic $\ce{KOH}$? Why does alcoholic $\ce{KOH}$ prefer elimination whereas aqueous $\ce{KOH}$ prefers substitution?
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Do alcohols react with alkyl halides?

I wonder if alkyl halides react with alcohols or not. I searched on Google but could only find reaction of alcohols with hydrogen halides
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Attack of ethoxide on epichlorohydrin

I eliminated the possibility of the first two options since they included an alcohol and the solvent has not been specified so we do not know whether it is polar protic or polar aprotic. As for the ...
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Which has one monochlorination possibility?

Which would have one monochlorination possibility? 2,2-dimethylpropane: or 2-methylpropane: It seems I'm missing something because I thought both would only have one monochlorination possibility. ...
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Does chlorine trifluoride react with candlewax?

I've run across references to chlorine trifluoride quite a lot. It pops up fairly regularly on the Worldbuilding SE, and whatever idea people have with it is usually shot down very quickly - For ...
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Will Chlorodifluoromethane (R22 refrigerant) react with calcium metal?

I am attempting to recycle or find a use for chlorodifluoromethane, however I do not want to risk venting it into the atmosphere or exposing myself to hydrofluoric acid. Ideally, I would like to ...
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Why is sulfur hexafluoride more stable than selenium or tellurium hexafluoride?

I was just reading about p Block elements from two different books. Both books say that $\ce{SF6}$ is extremely stable in 16th group due to steric reasons but my question is why is it more stable than ...
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Can you give examples for a halide ion reacting with interhalogen compound to give polyhalides?

Interhalogen compounds are formed when two halogens $(\ce{F},$ $\ce{Cl},$ $\ce{Br},$ $\ce{I})$ react together. They are represented by $\ce{XX'_n},$ where $\ce{X}$ is halogen of larger size and $\ce{X'...
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Why is the dipole moment of ethyl chloride larger than that of vinyl chloride?

The dipole moment of ethyl chloride is 2.10 D (J. Mol. Struct. 1990, 216, 9–26), and that of vinyl chloride is 1.42 D (J. Chem. Phys. 1960, 32 (1), 205–209). Why is this the case? I would have ...
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Why do we use hydrochloric in the test for sulfate ions but nitric acid for halide ions?

Recently, I have learnt about testing for ions in qualitative analysis (BBC Bitesize). The link above which I used for reference mentions that for the test for sulfate anions, hydrochloric acid $(\ce{...

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