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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32 views

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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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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127 views

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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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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271 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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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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76 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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241 views

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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225 views

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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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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Treating acetylene with excess HCl [duplicate]

Say we have been given acetylene with an excess of $\ce{HCl}$. In the first step of the reaction, $\ce{H2C=CHCl}$ is formed. But in the second step, there are two possibilities - gem-dihalide and a ...
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What is the mechanism followed in the hydrolysis of geminal dihalides using sodium hydroxide?

When a geminal dihalide is treated by alkaline $\ce{NaOH}$ we get a geminal diol which subsequently gets dehydrated to give carbonyl compounds. What type of mechanism is followed in this reaction? I ...
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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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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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(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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118 views

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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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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359 views

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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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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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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122 views

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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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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Intermediates in aqueous bromination of phenol

A question in my book asks: In the reaction: The intermediate(s) is/are? The correct answers are given as However, as per my knowledge, compound (b) does not appear in the reaction mechanism. Is ...
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149 views

Why is vicinal diiodopropane unstable, leading to deiodination?

I came across this reaction where simple electrophilic addition mechanism will result in a vic-diiodide. $$\ce{H2C=CH-CH2-I ->[HI, excess][CCl4]}$$ But the solution says that vicinal iodine groups ...
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Does KCN prefer SN2 or nucleophilic addition?

If we have a 1° halide that also contains a carbonyl group (like 5‐chloropentan‐2‐one), and we add 1 mole of KCN in DMSO to it, what will happen? Will the SN2 product by substitution of chlorine or ...
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Alkyl halides that do not undergo Wurtz reaction [duplicate]

I am aware that there are many limitations to the Wurtz reaction, notably the inability of 3° Halides to undergo SN² substitution. Instead, they undergo elimination. I came across a compound, 4-...
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Are Group 2 metal fluoride salts less soluble in organic solvents than Group 1 fluorides?

It is clear that Group 1 metal fluoride salts DO NOT readily form solutions in organic medium. The amount of solvation that can occur leading to the eventual release of a fluoride ion depends on many ...
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What qualifies to be considered as a lone pair-lone pair repulsion?

Referring to, NCERT Chemistry Part I, Textbook for Class XI[1]. Here the text puts forward three structures of $\ce{ClF3}$. My teacher said to me that (b) structure is unstable due to lone pair lone ...
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87 views

What would be the major products of this reaction?

Obviously, A would be 3-Bromoo 3-methyl cyclo hexene: as the stable free radical intermediate would be formed. But B is what I am having problems with. I read that $\ce{LiAlH4}$ forms alkenes with ...
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Adsorbable Organic Halides (AOXs) in bleach residue

I have a question regarding using household bleach, and wonder if someone knowledgeable can help, please? I have used household bleach (sodium hypochlorite, sodium hydroxide, coco alkyldimethyl, ...
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146 views

What is the IUPAC name of this organic compound? [closed]

Variety is the spice of life. I have made an organic compound myself. Can you please tell me the name? I thought that the correct answer is - 3,3-dibromo-2,4-dichloro-1,4-difluoro-2,4-diiodo-1-...
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Comparing of melting point of dibromo p-xylenes

How to compare the melting points of the above isomers? I know that melting point depends upon the packing of the molecule, more efficient the packing, higher is the melting point. Symmetry in a ...
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158 views

Why are halogens base sensitive groups (Wolff-Kishner Reduction)?

So while studying about Wolff-Kishner reduction reaction to form alkanes from carbonyl groups. I read that it is not suitable for base sensitive groups as the environment is highly basic and as an ...
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151 views

Why is the ionic radius of hydride so large?

The order of ionic radii for halides and hydride is apparently as follows: $$\ce{F-} < \ce{Cl-} < \ce{Br-} < \ce{H-} < \ce{I-}$$ Why is the hydride ion so large, even larger than bromide ...
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267 views

Which one of the following is NOT a haloalkane? [closed]

Which one of the following is NOT a haloalkane? A) Freon B) Teflon C) Iodoform D) Vinyl chloride Every compound here seems to me as a haloalkane: Freon, Teflon, iodoform, and vinyl chloride. My text ...
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Dehalogenation of vicinal dihalo alkanes

Which mechanism will the following reaction follow? Will it follow E2 mechanism? If yes, then how would 2,3-dibromobutane undergo this reaction? Does it form both cis and trans butene or is the ...
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323 views

Reaction of 1,3-dibromobutane with zinc dust upon heating

I've studied that when 1,3-dibromopropane (or in general any halogen, not just bromine) is heated with Zn dust, the electrons produced cause the halogens to break away homolytically and two free ...
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What makes a good chlorinating agent?

From what I know, good inorganic chlorinating agents, $\ce{SOCl2, PCl3, PCl5}$ are able to substitute a poorer leaving group (like $\ce{OH-}$) for chlorine. For example, for substitution of the ...
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832 views

Is HCl a lewis base?

Cl in HCl has three lone pairs of electrons. So it can donate a lone pair and thus become a lewis base. Right? Just like water is called a lewis base because oxygen has 2 lone pairs and can donate a ...
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182 views

Calcium chloride hydrolysis

I was wondering about $ \ce{CaCl2} $ hydrolysis. The most primitive answer would have been: $ \ce{Ca(OH)2} $ does not dilute that great, therefore it is not strong enough to have the $ \ce{Ca^2+} $s ...
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Why is density of chloroform greater than water?

Hydrocarbons (i.e., molecules containing carbon and hydrogen only) are generally less dense than water. Yet chloroform, which is a halogenated hydrocarbon, is more dense. Why is this? I know water ...
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Why does there need to be a planar intermediate in 2,2'-dibromobiphenyl when one of the phenyl groups rotates?

I was in class and my professor brought up the example of 2,2'-dibromobiphenyl: In her example, one of the bromines was actually pointing into the page and the two phenyl groups were not actually on ...
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Find the major products when these cyclohexenone bromides react with caustic potash in alcoholic medium:

Question: Also find the order of the rates of the given reactions. Answer: The answer of this question is given as option 'D' ie. all products are identical, however I am getting the answer as ...
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Lucas test in the presence of EWG like -CN

Does the given compound give Lucas test? My teacher says due to the presence of a strong electron withdrawing group the carbocation formed is unstable. But I say if it undergoes $\mathrm{S_N2}$ ...
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73 views

Contradiction of general rules of bond character [closed]

The rules the ionic character of metal halides of halogens is given in order $\ce{MF > MCl > MBr > MI}$. While judging polarisability we say that a compound that has large cation and small ...
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212 views

Reaction (or lack thereof) between oxygen and halogen gas

I understand that oxygen and halogens are both very electronegative elements and it would makes sense that they don't want to associate with each other at all. However, I know that oxides of halogens (...
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64 views

Predict the species formed by the reaction of mercury(II) chloride and iodine

$\ce{HgCl2}$ and $\ce{I2}$ both when dissolved in water containing $\ce{I-}$ ions the pair of species formed is A. $\ce{HgI2, I3-}$ B. $\ce{HgI2, I-}$ C. $\ce{HgI4^2-, I3-}$ D. $\ce{Hg2I2, I-}$ ...

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