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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5
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1answer
744 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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What is the mechanism of amination of aryl halide using cuprous oxide catalyst? [closed]

The simplified version of the reaction is $$\ce{Ph-Cl + 2 NH3 + Cu2O ->[\pu{200 °C}, \pu{150 atm}] Ph-NH2 + CuCl2 + H2O}.$$ I want to know its mechanism and the role of copper catalysis, and also ...
57
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1answer
8k views

Why does F replace the axial bond in PCl5?

Why does $\ce{F}$ replace an axial bond in $\ce{PCl5}$? I realize that it would be more stable there than at equatorial bond, but what is the reason of its stability? Similarly in $\ce{AB4}$ type of ...
4
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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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1answer
82 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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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 ...
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2answers
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Does fluorine ever form a double or triple bond?

Does fluorine ever form a double or triple bond? I wonder if seeming lack of such higher order bonds is related to the electronegativity of fluorine.
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2answers
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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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2answers
137 views

Why is density of chloroform greater than water? [closed]

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 ...
4
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1answer
260 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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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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The Action of Nitrogen Iodide on Methyl Ketones

I recently encountered two old publications on action of nitrogen iodide on various compounds (Ref.1 and Ref.2). Between them, Ref.1 described the idoform formation by methyl ketones upon treatment of ...
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2answers
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Products formed on cleavage of epoxides using HI

There seems to be multiple forms of $\ce{HI}$ used to cleave epoxides: conc. $\ce{HI}$, anhydrous $\ce{HI}$, cold $\ce{HI}$, hot $\ce{HI}$, cold conc. $\ce{HI}$, hot conc. $\ce{HI}$, etc. So, does ...
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Enthalpies of formation of alkali metal halides

Shriver and Atkins's Inorganic Chemistry has this graph: How can I explain the different direction of the trends for fluorides and chlorides? I know that the decreasing lattice energy (as M goes from ...
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3answers
215 views

Stability of α-chlorocarbocations

I'm trying to compare the relative stability of two carbocations: $$\ce{CH3-\overset{+}{C}H-Cl}\quad\text{vs}\quad\ce{CH3-\overset{+}{C}H2}$$ Does the $\ce{Cl}$ exert a +M effect to stabilise the ...
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0answers
35 views

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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1answer
600 views

In the Lewis structure for barium fluoride, why does barium lose its valence electrons?

I searched for $\ce{BaF2}$ Lewis structure, and found out that the Barium atom loses its 2 valence electrons to form $\ce{F- Ba^2+F-}$. Before seeing it I thought each of $\ce{Ba}$'s valence electrons ...
3
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4answers
7k views

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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1answer
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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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2answers
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Why are two three-membered rings preferred to a single five-membered ring in the reaction of a dihalide with alcoholic KOH?

The given answer is 1,1-dicyclopropylmethanone: Step 1 is abstraction of acidic H by the strong base. Then, there's surely going to be anchimeric assistance. But there can be two places where the ...
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1answer
162 views

Wittig reaction with an alkyl dibromide

Recently, I have come across a problem, in which a ketone needs to be converted into an alkene. However, in the alkene product, there is also another bromide functional group, at the end of the alkyl ...
5
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1answer
6k views

Why doesn't NF₃ undergo hydrolysis?

I was reading Jan's answer to the following question-: Why can NCl3 be hydrolyzed but CCl4 cannot?. Since nitrogen is less electronegative than fluorine in $\ce{NF3}$, the electrophilic site is the ...
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1answer
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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 (...
4
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1answer
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Structure of xenon hexafluoride

The central atom has a hybridization of $\mathrm{sp^3d^3}$. Thus, its structure should be pentagonal bipyramidal. Why is it not that but a distorted octahedron?
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2answers
263 views

Mechansim of reaction between 1‐bromo‐2‐fluorobenzene and furan in the presence of Li/Hg

Problem From FITJEE AITS test series: What is the mechanism of the following reaction? Solution My approach It looks like Birch reduction with $\ce{Li}$ converting to $\ce{Li+}.$ But I can't make ...
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4answers
356 views

Most favorable position of attack of an electrophile on 4-trifluoromethyl-1,2-diphenylbenzene

Problem This problem is from a FIITJEE AITS paper Which position is most favorable for the attack of an electrophile? Answer My attempt The more favorable position for attack should be the on the ...
11
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4answers
3k views

Reasons for negative iodoform test

Why does 2',6'-dimethylacetophenone not give iodoform test?
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1answer
45 views

Will a reverse osmosis membrane exclude perfluorobutanoic acid?

I recently did a water quality test and it showed a detectable level of perfluorobutanoic acid, a potentially dangerous carboxylate PFC. Will a reverse osmosis water purification system exclude this ...
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1answer
47 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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0answers
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Preparing Hypochlorous acid from salt water

I am a school student and I want help with a project My aim: Preparing Hypochlorous Acid (Suitable for sanitation). I searched across the internet and found an article at https://www.hypochlorousacid....
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7answers
24k views

The solubility of haloalkanes in water

Haloalkanes aren't very soluble in water because they can't form hydrogen bonds, and the energy required to break hydrogen bonds in water etc is higher than the energy released when new bonds between ...
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1answer
114 views

Reaction of 2,3-dichlorobutanoate with a decarboxylating agent followed by hydrochloric acid and then aq. potassium hydroxide

Question $$\ce{CH3-CH(Cl)-CH(Cl)-COO- ->[-CO2]A->[HCl]B->[aq KOH]C}$$ Product C is: a) $\ce{CH3-CH2-CHO}$ b) $\ce{CH3-CH(OH)-CH2-CH2-OH}$ c) $\ce{CH3-CHO}$ d)$\ce{CH3-C(=O)-CH3}$ Answer My ...
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1answer
63 views

Why is polonium tetrafluoride non-existent?

I learnt that the group 16 elements can form halides, but with the exception that polonium cannot form a tetrahalide with fluorine. However, I thought that it was possible. This is because the ...
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0answers
89 views

What is the correct formula for iodonium ion?

Previously, I have made a comment on user @Maurice's response to a question where he enquired about the existence of $\ce{I3+}$. I cited a paper1 which said that $\ce{I3+}$ is (apparently?) called ...
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1answer
75 views

Relative reactivity of alkyl and aryl halides in nucleophilic-substitution reactions

In case of alkyl halides, the order for relative rates of reactions is $\ce{RI > RBr > RCl}$. The reason is clear that $\ce{I-}$ is a better lg because of negative charge stabilisation and also $...
2
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1answer
171 views

Reaction of alc. KOH with alkyl halide

The following question was given in FIITJEE study material: At first, I thought it should be elimination. But, soon I realized that there is no heating, plus a primary alkyl halide is used. So, "...
0
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1answer
74 views

Why HCl is used in Lucas test?

In Lucas test $\ce{HCl}$ is used for acid-base reaction between $\ce{Zn(OH)Cl}$ to give $\ce{ZnCl2}$ and $\ce{H2O}$ which is kind of good because $\ce{ZnCl2}$ is formed again and used in first step ...
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1answer
44 views

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 ...
5
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1answer
499 views

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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2answers
121 views

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- ...
5
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1answer
359 views

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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2answers
719 views

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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0answers
49 views

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 ...
2
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0answers
49 views

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 ...
3
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2answers
65 views

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 $\mathrm{S_N2}$...
6
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1answer
27k 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 ...
1
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1answer
216 views

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 ...
5
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3answers
339 views

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 ...
4
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1answer
2k views

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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