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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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12
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1answer
157 views

Products formed on cleavage of epoxides using HI

There seems to be multiple forms of HI used to cleave epoxides: conc. HI, anhydrous HI, cold HI, hot HI, cold conc. HI, hot conc. HI, etc. So, does concentration of HI and temperature have any ...
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359 views

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 ...
7
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149 views

How can I solve this synthesis?

I have this task to do: My solution: Is that possible? Can you please help me with the steps 2 and 3? This is what I did, but my teacher told me I should make the diketone (compound no. 5) from ...
7
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877 views

Why does magnesium prefer to insert into C–Br bonds over C–Cl bonds?

In the formation of a Grignard reagent from a compound possessing both bromine and chlorine, magnesium preferentially inserts into the C–Br bond over the C–Cl bond. For example, the formation of a ...
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255 views

Why do chlorinated silanes have lower boiling points than their methane analogs?

The boiling points of the chlorinated silanes and methanes are given below: $$\begin{array}{ccc} \hline \text{Species} & \text{Boiling point (X = Si) / }\mathrm{^\circ C} & \text{Boiling ...
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722 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 ...
6
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1answer
647 views

Can an SN1 reaction occur in compounds with the leaving group attached to a primary carbon, which can later rearrange?

Can SN1 reactions occur in compounds where the carbocation, even though is is initially $1^\circ$, can rearrange to form a more stable carbocation? Examples cases:
5
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0answers
227 views

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 ...
5
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0answers
258 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 ...
5
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0answers
212 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 ...
5
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0answers
691 views

Why PI3 is not used in HVZ 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 ...
5
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1answer
794 views

Bromination of alkenes

In regard to the mechanism of halogen addition, consider the situation when we add a halogen (say, bromine) to an unsymmetrical alkene about the double bond (say, propene) in the presence of $\ce{CCl4}...
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248 views

Mechanism for reaction of enol ether with HBr

Please refer to the image for the question. I tried two different mechanisms for the reaction (1 and 2) and ended up with two different products. Now I can't decide which of the two mechanisms would ...
4
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0answers
1k views

What is the SNi mechanism of the reaction of moist silver oxide with a halide?

I was told by my teacher that the following reaction proceeds through SNi: Moist $\ce{Ag2O}$ is basically $\ce{AgOH}$, what role does it play in this reaction's mechanism? I think this is what ...
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386 views

Hydrogen bond strength of trichloromethane and chloromethane

Chloromethane has a larger dipole moment than trichloromethane. Does that mean that the hydrogen bond (C-H...O type) between chloromethane and acetone is stronger than that of trichloromethane and ...
4
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333 views

Textbook suggests secondary alkyl halides do not undergo SN1 reaction

The 8th edition of Organic Chemistry by Paula Bruice suggests that secondary alkyl halides do not undergo SN2 reactions. However, many other sources state the opposite. So, what is the correct answer? ...
4
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1answer
2k views

Titanium in HF vs HCl

So we tried the reaction between Titanium metal with hydrochloric acid and hydrofluoric acid at a similar concentration. While boiling temperatures and constant heat over a long period of time are ...
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187 views

Abnormal reaction of grignard reagent

My book states that: When isopropyl magnesium bromide is added to diisopropyl ketone, the expected tertiary alcohol is not obtained; instead the secondary alcohol; diisopropyl carbinol is obtained ...
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0answers
39 views

Do 2-aminoalkanes undergo iodoform test?

I was doing problems in an excercise book and they gave a list of compounds that may undergo iodoform test- which included 2-aminoalkanes. I dont find any keto methyl gps or methyl carbinol gps that ...
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553 views

Why is the silver nitrate chemical test more favorable than that of sodium iodide?

Two tests to determine the presence of alkyl chlorides are the silver nitrate in 1% ethanol and sodium iodide in 15% acetone tests. These two tests both produce a precipitate when added to chloride ...
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235 views

Mechanism for conversion of gem-dihalide to carbonyl compound

How does nucleophilic substitution work in a compound consisting of two leaving groups? I understand that hydroxide ions will attack the carbon centre (which bears a partial positive charge) and ...
3
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0answers
50 views

Can iodine hydrocarbons be used as fire extinguishing agent? What are their properties?

In the German Wikipedia the following claim about fire extinguishing agents is made: Iodkohlenwasserstoffe haben zwar eine hervorragende Löschwirkung, erlangten wegen ihres exorbitant hohen ...
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46 views

Can the directionality of an SN2 reaction depend on solvent polarity?

Because of the effects of solvation, halide ions have differing nucleophilicity in protic solvents vs aprotic solvents, iodide being the best nucleophile in protic solvents and fluoride being best in ...
3
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0answers
1k views

Gilman Reagent with vinyl chloride

What are the products formed when vinyl chloride reacts with dimethyl copper? I thought the product formed would be propene. But answer given is PolyVinylChloride. How does polymerization take place?
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40 views

Elimination with Amines

$\hspace{35 mm}$ ATTEMPT: Since $\ce{Et3N}$ is a weak base and the carbon to which $\ce{Br}$ is attached is tertiary, we can rule out $\mathrm{E2}$ and $\mathrm{S_N2}.$ As we are providing heat, the ...
3
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1answer
551 views

Why is methyl iodide more dense than ethyl iodide, even though the latter has more carbon atoms?

It is understood that more carbon atoms present in a hydrocarbon, the greater the density of the hydrocarbon. But then why does $\mathrm{CH_{3}I}$ have a greater density than $\mathrm{C_{2}H_{5}I}$?
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504 views

OF2 vs O2F2 oxidising strength

My teacher said that OF2 is the third most powerful oxidising agent after F2 and atomic O, but I think O2F2 should be even more oxidising, since it less stable than OF2. I just read on quora that O2F2 ...
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438 views

Reactivity and selectivity in free radical halogenation of alkanes

I read about the free radical halogenation of alkanes with $\ce{X2}$ and I have the following questions: Given that the first step is the homolytic breaking of the $\ce{X-X}$ bond, and the homolytic ...
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70 views

Results of mixing HSbF6 and O2F2

I'm an amateur writer and one of the topics I deal with is what happens when a slightly-mad scientist and engineer is given an opportunity to work with full-on “magic.” So there are situations where ...
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0answers
765 views

Is benzyl chloride or allyl chloride more reactive?

What compound is more reactive, benzyl chloride [(chloromethyl)benzene] or allyl chloride (3-chloroprop-1-ene)? I know that both have a higher reactivity than alkyl and aryl chlorides.
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86 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 ...
2
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0answers
56 views

Why do reactions of sodium halides with sulfuric acid produce sodium hydrogen sulfate instead of sodium sulfate?

In the reaction of sodium halides with sulfuric acid, sodium hydrogen sulfate is produced \eqref{NaHSO4}. Why would this be produced instead of sodium sulfate \eqref{Na2SO4}? \begin{align} \ce{NaX + ...
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0answers
88 views

How to perform oxidation of keto group in presence of hydroxyl group?

How to perform oxidation of keto group in presence of hydroxyl group. I fear there may be halogenation at $\ce{OH}$ group. Is there a way to protect the $\ce{OH}$ group ?
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86 views

Does acetophenone show haloform reaction?

Although acetophenone is a methyl ketone, as it is aromatic, it is immiscible in H2O so the last step in the haloform reaction should not occur? I couldn't find any source regarding the haloform ...
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0answers
83 views

Reaction of Br2/KOH with succinic anhydride

What products will be formed when $\ce{Br2/KOH}$ reacts with the following compound in water at room temperature? Here is what I think is possible: $\ce{OH-}$ will take up the acidic hydrogen. ...
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0answers
50 views

Difference between reactions of ring strained cycloalkanes and higher cycloalkanes (n>4)

Today I read two publications stating that cyclopropane's ring can be opened by reactions of it with $\ce{Cl2/Br2/HCl/HBr}$. Correct me please if I interpreted something wrong. Here are these ...
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0answers
296 views

What is the product formed when 4-chlorobut-1-ene is treated with acetic acid?

My teacher did like this forming a really unstable cyclopropyl group but this is the correct answer instead. My question is why the product will be even formed? In the mechanism that my teacher had ...
1
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0answers
123 views

Anomalous trend in formation enthalpy of alkali metal halides

I read that in alkali metal halides, the formation enthalpy for fluorides become less negative as we go down the group, whereas the reverse is true for chlorides, bromides and iodides. Why is it so? ...
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0answers
258 views

How to compare the reactivity of sec-butyl iodide and n-butyl bromide for SN2?

Steric crowding is greater for the secondary halide, and this is important as the neucleophile will attack the back lobe of carbon atom. But the relative ability to leave is more for iodide than ...
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0answers
102 views

Halogens and Equilibrium

Suppose 1 mol of $\ce{KI (aq)}$ is mixed with $\pu{1 mol}$ of $\ce{I_2^*}$, where $\ce{I_2^*}$ represents a di-iodine molecule which has been radioactively labelled, and the substances are allowed to ...
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0answers
125 views

What is the product of the reaction of 2-bromo-1-fluoro-4-nitrobenzene with sodium methanethiolate?

In the reaction depicted below shouldn't $\ce{Br}$ be replaced by $\ce{SCH3-}$ ion as $\ce{Br-}$ is a good leaving group and the $\ce{C-F}$ bond is quite strong due to back bonding of 2pπ-2pπ orbitals?...
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0answers
99 views

Synthesis of para-chloroanisole using diazotisation followed by chlorination with aluminium chloride

Is this a legitimate reaction scheme to synthesise para-chloroanisole from benzene and methanol as the only organic reactants? $$\ce{C6H6 -> HNO3/H2SO4 -> H2/Pd -> HONO/{Ethanol}\\ -> {...
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0answers
233 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 ...
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0answers
42 views

Why do electrophillic addition reactions (between hydrogen halides and alkenes) happen?

I understand that the type of solvent (protic or aprotic) may impact the rate of the reaction, but why doesn't the hydrogen just stick with the halide in the first place? I'm not sure if the reason ...
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0answers
336 views

In electrolysis, why is hydroxide oxidised in preference to anything(?) but halides?

In electrolysis of aqueous solutions, I can loosely explain what happens at the cathode in terms of reactivity - any metal more reactive than hydrogen stays in solution, effectively because they're ...
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0answers
127 views

CuCl via electrolysis of HCl

I need a solution of CuCl in HCl. Since CuCl reagent is such a pain to source and work with (because it oxidizes so quickly) I was thinking that I could create the solution simply via electrolysis of ...
1
vote
1answer
812 views

Isn't the mechanism of aqueous sodium hydroxide and 1-bromobutane involves both heterolytic bond fission and attacking by a nucleophile?

What is involved in the mechanism of the reaction between aqueous sodium hydroxide and 1-bromobutane? A. attack by a nucleophile on a carbon atom with a partial positive charge B. heterolytic bond ...
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0answers
31 views

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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0answers
40 views

Reaction rate of Mg with aryl halides

I have been thinking of the rate of reaction of aryl bromide and aryl chloride with $\ce{Mg}$ to form Grignard. When considering the electronegativities the carbon in aryl chloride is more ...
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0answers
17 views

How would one determine the yield of primary vs. secondary hydrohalogenation addition products?

For example, if I was to perform the following reaction: $\ce{CH3CHCH2 + HBr -> CH3CHBrCH3 + CH3CH2CH2Br}$ How would I quantitatively determine the relative yield of the primary and secondary ...