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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3
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1answer
135 views

What is the IUPAC name for this compound containing a phenyl group attached to it?

What is the IUPAC name for the compound $\ce{(CH3)3CCH2CH(Br)C6H5}$? The answer I got myself was (1-Bromo-3,3-dimethylbutyl)benzene, but from looking online most sources list the name as 1-Bromo-3,3-...
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240 views

How can I convert 3-bromocyclohexene to cyclohexane?

My attempt: or Which one of the methods seems viable?
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1answer
50 views

SN1 reaction of alkyl halides

I was going through Peter Sykes organic chemistry where I came across a section where the author is saying: For halides that do not readily undergo SN1 attack ,this can be promoted by use of silver ...
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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{I2Cl6}...
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1answer
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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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33 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, ...
6
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2answers
339 views

Darzens reaction on allylic position

Question Attempt I thought the products would be from simple darzens reaction. So I replaced the $\ce{OH}$ by $\ce{Cl}$. But the answer of mine seems way wrong. Do give some tips on what might be ...
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4answers
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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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1answer
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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2answers
56 views

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 ...
2
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1answer
192 views

How to rationalise differences in halogen bonding?

Please see the problem in this link. I understand the explanation in (c), but it appears to me, that accepting that would contradict the answers to parts (a), (b), and (c). Is the reason for part (a) ...
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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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1answer
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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1answer
121 views

Detection of NaF levels in aqueous solution also containing NaCl

Is it possible to determine the concentration of sodium fluoride, more specifically fluoride ions, in a solution that also contains sodium chloride? I have looked into using an ion-specific electrode, ...
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2answers
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Why is WF6 stable whereas CrF6 is unknown?

$\ce{F-}$ is a hard base since it is small and relatively polarizable. Both $\ce{Cr^6+}$ and $\ce{W^6+}$ are hard acids, but shouldn't $\ce{CrF6}$ be favored since it would be a smaller hard acid?
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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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1answer
325 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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1answer
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How can AuCl3 exist?

The reduction potential for $\ce{Au^3+ + 3e- -> Au}$ is $1.503 \text{ V}$. The reduction potential of $\ce{Cl2 + 2e- -> 2Cl-}$ is $1.36 \text{ V}$. So, the $E^o$ for $\ce{2Au^3+ + 6Cl- -> 2Au ...
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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 ...
5
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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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1answer
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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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1answer
62 views

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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43 views

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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2answers
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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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1answer
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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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1answer
119 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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1answer
361 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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1answer
554 views

Why does bromide not react with water when methyl ammonium bromide is dissolved in water?

In the following reaction, the salt $\ce{CH3NH3Br}$ is formed: $$\ce{CH3NH2 + HBr -> CH3NH3Br} $$ In water this dissociates completely into $\ce{CH3NH3+}$ and $\ce{Br-}$ In my chemistry book, it ...
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1answer
88 views

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 ...
6
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1answer
519 views

Is the haloform reaction possible with fluorine and pseudohalogens also?

The haloform reaction is: $$\ce{RCOCH3 +3X2 +4OH^- -> RCOO^- +CHX3 + 3X- + 3H2O}$$ where, $\ce{X}$ is $\ce{Cl}$, $\ce{Br}$, or $\ce{I}$. However, I was wondering if this reaction works with ...
2
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1answer
6k views

Predicting order of nucleophilic substitution reactivity

What order of reactivity do you predict will be observed when each alkyl halide is mixed with sodium iodide in acetone? 1-Chlorobutane 1-Bromobutane 2-Chloro-2-methylpropane Bromobenzene ...
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1answer
156 views

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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1answer
2k views

Hydrogen halide acidity

Why is it that $$\mathrm{p}K_\mathrm{a}(\ce{HF}) < \mathrm{p}K_\mathrm{a}(\ce{HCl}) < \mathrm{p}K_\mathrm{a}(\ce{HBr}) < \mathrm{p}K_\mathrm{a}(\ce{HI}),$$ even though the electronegativity ...
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1answer
150 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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40 views

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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1answer
410 views

(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 ...
3
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1answer
101 views

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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2answers
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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 ...
4
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1answer
123 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 ...
6
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1answer
30k views

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 ...
2
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1answer
74 views

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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1answer
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Why do the boiling and melting points decrease as you go down group 1 and vice versa for group 7?

I used to think that because an alkali metal needs to lose one electron to complete its outer shell, when the atom increases in size (atomic radius), the electron would be easier to lose as the ...
2
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1answer
66 views

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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3answers
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Order of Basicity of Nitrogen Trihalides

I was asked to arrange nitrogen tri-halides in order of increasing basicity. On looking up the answer online, it turned out to be the following: $\ce{NF3}$ < $\ce{NCl3}$ < $\ce{NBr3}$ < $\ce{...
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2answers
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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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1answer
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Why is fluorine more reactive than iodine despite the weaker I-I bond?

The atomic radius of halogens increases as we go down the group due to the addition of new shells. As a result, the bond length of halogen $\ce{X-X}$ increases down the group. So, less energy is ...
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Can we use phosphorous triiodide in Hell-Volhard-Zelinsky reaction?

With the help of HVZ reaction, we can get alpha-chloro or alpha-bromo carboxylic acid. But can we make alpha-iodocarboxylic acid with the help of HVZ reaction? I could not find any reference of HVZ ...

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