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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9
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1answer
948 views

Why don't hydride shifts occur with hydrohalogenation of 4-methyl-cyclohexene?

My book (see bottom) implies that hydrohalogenation of 4-methyl-cyclohexene follows this mechanism: Why not undergo consecutive hydride shifts to furnish a tertiary carbocation? I would guess that ...
5
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1answer
120 views

Degradation of sulfuryl fluoride SO2F2

Recently, the houses next to us were fumigated with "Vikane", which apparently is $\ce{SO2F2}$. To my surprise, the gas was just pumped out in the atmosphere without further ado at the end of the ...
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2answers
5k views

How to write the redox reaction of chlorate to chlorine and oxygen using half rections?

I know how to solve redox reactions, but this one is really confusing me since I can't really write half reactions for it. $$\ce{ClO3- -> Cl2 + O2}$$ The answer is apparently: $$\ce{2H+ + 2ClO3- ...
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1answer
2k views

Does Finkelstein's reaction proceed through an SN2 mechanism?

I was dealing with a question whose answer was justified only when it was assumed that the Finkelstein reaction proceeds through an $\mathrm{S_N2}$ mechanism. So, does it really follow an $\mathrm{...
8
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1answer
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Does (chloromethoxy)ethane react in a bimolecular or monomolecular mechanism?

It is known that (chloromethoxy)ethane forms stable carbonium ions based on Nobel prize Chemist George Olah research Olah's method. This would indicate that (chloromethoxy)ethane reacts through $\...
3
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2answers
118 views

Which hydrogen halides react with group 14 oxides?

$$\ce{6HF +SiO2->H2SiF6 +2H2O}$$ $\ce{HF}$ reacts with $\ce{SiO2}$ to form $\ce{H2SiF6}$. Do other hydrogen halides like $\ce{HCl}$ and $\ce{HBr}$ react with group 14 oxides in the same way?
1
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1answer
230 views

Why is the ester bond stable under Reformatsky reaction conditions?

The following reaction is a Reformatsky reaction. Why is the ester bond not attacked in the last step? Couldn’t $\ce{OR3}$ be replaced by $\ce{OH}$ or $\ce{O(molecule)}$?
5
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3answers
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Why does chloromethane have a larger dipole moment than chloroform?

Why does $\ce{CH3Cl}$, methyl chloride, have a larger dipole moment than $\ce{CHCl3}$, chloroform? Let us consider $\ce{C-Cl}$ bond moment to be $x$ and that of $\ce{C-H}$ bond to be $y$. In $\...
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1answer
2k views

Why does thallium form TlF and TlF3 but aluminium only forms AlF3?

Does this have something to do with the inert pair effect?
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1answer
49 views

Hydrolysing a compound by repeated methyl and hydride shifts

The question is to predict the major product in the following reaction. First of all the proton will abstract the bromide ion resulting in the formation of a primary carbocation which being unstable ...
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1answer
6k views

Why is the carbon-fluorine bond stronger than the other haloalkanes? [closed]

What effect makes C-F bond stronger than other halo-alkanes?
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1answer
967 views

Hydrolysis of Phosphorus Trichloride

During hydrolysis of a halide of carbon via $\mathrm{S_N2}$ mechanism, the incoming neutral water molecule attacks the partially positive carbon centre from the side opposite to the halide side and ...
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1answer
4k views

By which mechanism would azide react with alcohols or alkyl halides?

$\ce{NaN3}$ produces $\ce{N3-}$ ions. So the reaction with an alkyl halide will either be $\mathrm{S_N1}$ or $\mathrm{S_N2}$. After some reading, I found that $\ce{N3-}$ is a good nucleophile. Hence ...
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1answer
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Carbon-13 NMR for chloroform

I am slightly confused by what the spectrum would show for carbon-13 NMR of $\ce{CHCl3}$. My initial guess would be that the peak would be split by coupling to both the proton and the 3 chlorines, as ...
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3answers
612 views

Skeletal formula of methyl chloride

Recently in The Periodic Table, there was a short discussion regarding this structure: At first sight, I couldn't figure out what is the structure. After a quick google search, I came to know it is ...
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1answer
6k views

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 ...
4
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1answer
401 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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1answer
85 views

C-H bond energy in substituted methanes

What happens to the $\ce{C-H}$ bond strength in methane as the degree of halogenation is increased (e.g. from $\ce{CH4}$ to $\ce{CH3X}$ to $\ce{CH2X2}$...) Also, what is the effect of varying the ...
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2answers
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Why is caesium considered the most reactive element and not fluorine? [closed]

Some people say caesium is most reactive element. I thought it to be fluorine as it is the element that reacts with almost all elements (except couple of inert gases). But caesium won't react many of ...
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2answers
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Why do halogen substituents make molecules more lipophilic?

According to my medicinal chemistry text book, halogens increase a drug’s lipophilicty. This makes no sense to me for two reasons: Halogens are all quite electronegative and they will form a $\ce{C-X}...
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2answers
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Should carbon tetrachloride really be considered an organic compound?

Wikipedia says: Carbon tetrachloride […] is an organic compound with the chemical formula $\ce{CCl4}$. From an organic point of view, carbon tetrachloride can be called the tetrachloro ...
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2answers
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Fluorine Preparation:How can this be explained on basis of Lewis Acid-Base Reaction?

How can this be explained on basis of Lewis Acid-Base Reaction ? $\ce{2 K2MnF6 + 4 SbF5 → 4 KSbF6 + 2 MnF3 + F2↑}$ References: https://en.wikipedia.org/wiki/Fluorine#Industrial Google Books ...
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1answer
128 views

In a mass spectrum, are there peaks corresponding to a combination of 13C and bromine isotopes?

I just began studying mass spectroscopy and I don't understand why certain peaks are not represented in the mass spectrum graph. Like let's say you have methyl or ethyl bromide. Usually, there are two ...
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1answer
391 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
412 views

Why does hydroxide attack the carbon atom of methyl iodide (in an Sn2 reaction)?

As the electronegativity difference between carbon and iodine is negligible, why does $\ce{OH-}$ attack the carbon atom (in an $\mathrm{S_N2}$ mechanism) even though carbon doesn't seem to be ...
11
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1answer
968 views

In the Favorskii rearrangement, why doesn't the base grab the alpha hydrogen of the carbon bearing the halogen?

In the Favorskii rearrangement, the base (like hydroxide) always abstracts the alpha hydrogen of the carbon not bearing the halogen. But to me the hydrogens on the carbon directly connected to the ...
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0answers
241 views

Why are alkyl halides immiscible with water?

Why are alkyl halides, though polar, immiscible with water? I have tried to solve this question by myself and I believe that it's due to the large energy is needed to break the hydrogen bonds, which ...
3
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1answer
277 views

Reason for decreased boiling point of hexafluoroisoproponal?

Ethanol and isopropyl alcohol have boiling points 78.37 °C and 82.6 °C respectively. The increase in the boiling point is obvious due to increase in carbon chain length which resulted in increase in ...
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2answers
11k views

Bromination of acetanilide

Why does acetanilide gives exclusively para isomer. I know that -I of nitrogen must decrease the yield of ortho product, but still it should be made in accountable amounts. Where am I going wrong. I ...
4
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2answers
40 views

Best reagents state for air free chemistry. Choosing halide for grignard synthesis

I am planning to synthesize a grignard and I have a choice between the iodo or chloro aryl halide. The iodo is a solid and the chloro is borderline. For my previous reaction I melted the chloro and ...
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1answer
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Thermal stability of interhalogen compounds

I am striving over the question that what would be the stability order of the following interhalogen compounds : $\ce{ClF3, BrF3}$ and $\ce{IF3}$. One probable answer I got is that stability of ...
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1answer
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Iodine test for Starch

The starch and iodide test is to detect amylose, a polysaccharide. We add an iodide solution to a sample and observe a color change with the starch; it turns dark blue. While researching information ...
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2answers
183 views

Acid catalysed bond hydrolysis in 3-bromobut-1-ene

I came across this doubt while solving a problem. I can't understand to which path (1 or 2) I should give priority, as both sound equally good to me.
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3answers
945 views

Predict which hydrogen is more acidic in the following organic compounds?

Between 2-chloro-2-phenylpropionic acid and hydrogen phthalate, which is the more acidic compound? I'd say the $\ce{H}$ on the second one is more acidic as the $\ce{-COOH}$ group is directly attached ...
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1answer
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Why is it possible to form bromoalkanes but not iodoalkanes from free radical substitution?

For a free radical substitution (FRS) reaction between iodine $\ce{I2}$ with ethane and bromine $\ce{Br2}$ with ethane $\ce{CH3CH3}$: $E_\mathrm d(\ce{H-I})=299\ \mathrm{kJ\ mol^{-1}}$ $E_\mathrm d(\...
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1answer
2k views

Free radical substitution - bromination of ethane

I am new to this service so please overlook any mistakes. My question is with regards to free radical substitution. I understand the three step process of the bromination of ethane and what would ...
11
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1answer
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Why is KI oxidized by H2SO4, whereas NaBr isn't oxidised?

My textbook says that alcohols react with sodium bromide and sulphuric acid to form the corresponding alkyl bromides. At the same time they also mention that sulphuric acid mustn't be used with ...
8
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1answer
411 views

Can thionyl bromide produce alkyl bromides?

Thionyl chloride ($\ce{SOCl2}$) is used with alcohols to produce alkyl chlorides. Similarly, can thionyl bromide ($\ce{SOBr2}$) be used with alcohols to produce alkyl bromides?
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1answer
282 views

Is it possible for halogens to show oxidation states less than -1?

Halogens like $\ce{Cl,Br,I}$ generally show oxidation states between $-1$ and $+7$. However, is it possible that they can show an oxidation state beyond $-1$ (e.g. $-3$)? I was thinking of some ...
4
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1answer
2k views

Why is no bromine liberated in the reaction of potassium bromide and concentrated phosphoric acid?

$\ce{KBr}$ reacts with concentrated $\ce{H3PO4}$ to give $\ce{HBr}$ and ($\ce{KH2PO4}$ or $\ce{K3PO4}$) (not sure which one, if someone knows it, please tell). Why isn't bromine gas liberated?
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1answer
607 views

Why do the halogenations of benzene and toluene lead to different products?

The reaction of benzene with $\ce{Cl2}$ in presence of sunlight breaks the double bonds and 6 chlorine atoms attach to the ring. However, the same reaction done with toluene does not lead to ...
5
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2answers
752 views

Does the compound KFO₃ exist?

As the compound potassium chlorate exists, is there something as $\ce{KFO3}$? All the other halogenates are mentioned somewhere on the web but what about this? If no, then why?
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2answers
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Why do higher fluorine oxyanions not exist? [duplicate]

I asked this question from my teacher and he said that's because fluorine has a high electronegativity and does not form dative bond with oxygen. That's why only hypofluorite $\ce{FO-}$ exists and not ...
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0answers
87 views

What determines whether iodination or reduction will occur?

Alkyl Iodides are formed by reaction of alcohols with iodine and red phosphorus. I already am well aware that this forms $\ce{PI3}$ in situ, which acts similarly to $\ce{PBr3}$ and allows alkyl ...
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0answers
751 views

Mechanism for the decomposition of HI

I've been trying to find the mechanism for the gas phase decomposition of hydrogen iodide: $$\ce{ 2 HI (g) <=> H2 (g) + I2 (g)} $$ Anyone know of sources where I can get information on this? I ...
2
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1answer
251 views

How can weaker nucleophiles kick out stronger ones in the reaction of chloroalkanes with sodium iodide in acetone?

I have the following SN2 reaction, in an acetone: 1,4-dichlorohexane (1 mol) reacting with NaI (1 mol) to form 4-chloro-1-iodohexane and NaCl. However, chloride ions are stronger nucleophiles than ...
2
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2answers
2k views

Regioselectivity of alpha halogenation of ketones

Why does alpha halogenation of a ketone in acidic conditions happen at the more substituted alpha carbon atom, and in basic conditions at the less substituted alpha carbon atom?
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1answer
4k views

Major Product of Alkene in Bromine Water

At school, we are taught that in bromine water, the following equilibrium is present: $$\ce{Br2 + H2O \rightleftharpoons BrOH + HBr}$$ Therefore, when you add an alkene to bromine water, you don't get ...
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1answer
2k views

NaI in acetone v/s acetone and water

When NaI is in acetone and we have R-X, then I replaces X by Finklestein mechanism (Sn2 => Inversion). But when we have acetone and water, why do we get a racemic mixture?
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1answer
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What happens when potassium iodide is added to a copper (II) salt?

$$\ce{Cu^2+ + KI -> ??}$$ I thought of this reaction: $$\ce{Cu^2+ + 2KI -> CuI2 + 2K+}$$ But since $\ce{CuI2}$ doesn't exist, the $\ce{I-}$ ions must reduce $\ce{Cu^2+}$ to $\ce{CuI}$ and ...