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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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5
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3answers
500 views

Substitution at thionyl chloride sulfur

What is the correct way of writing the mechanism for substitution at the sulfur atom of thionyl chloride: Should one write the cleavage of the $\ce{S-O}$ π bond? The argument for the first ...
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1answer
906 views

Sodium fluoride and varying pH - HF risk [closed]

I'm looking into conducting an experiment on the adsorption of fluoride (for my International Baccalaureate Extended Essay). As I will be investigating the role of $\mathrm{pH}$ in adsorption capacity,...
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1answer
191 views

Alkyl halide reaction

In the following the reaction , According to me the product should be compound (A) due to substitution reaction. But the product formed is the compound (B) , what could be the mechanism for the ...
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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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2answers
614 views

Synthesis of bromobutane

What will be the cost efficient and high yielding method of synthesis for 1-bromobutane? I can react butanol with $\ce{HBr}$ but I am worried butanol is not present at the moment in lab. But I need ...
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2answers
8k views

Reactivity towards SN1 reaction

In the following compounds , we have to find order of compounds of their reactivity towards SN1 reaction. According to me , we should compare carbo cation stability which is formed as an ...
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1answer
66 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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1answer
8k views

What is the structure of iodide of Millon's base?

In qualitative analysis, $\ce{NH4+}$ ions are confirmed using Nessler's reagent:- $$\ce{NH4+ + 2[HgI4]^{2−} + 4OH− → HgO·Hg(NH2)I ↓ + 7I^{−} + 3H2O}$$ The brown precipitate ...
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1answer
1k views

Why does iodine have different colors in different media?

It is violet in trichloromethane, but brown in water. why? In the Shriver Atkins book, they tried to explain this using Molecular Orbital Theory which was not clear to me
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1answer
629 views

Why triiodide ion does not form ionic bond with cation having +2 charge?

In general, I found that triiodide ion generally forms ionic bond with cations having +1 charge like $\ce{NH4+I3-}$, $\ce{K+I3-}$, $\ce{Tl+I3-}$. But, I have never seen triiodide ion forming ionic ...
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1answer
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Hydrogen halide acidity

Why is it that $pK_{\ce{a-HF}} \lt pK_{\ce{a-HCl}}\lt pK_{\ce{a-HBr}}\lt pK_{\ce{a-HI}}$, although the electronegativity decreases? The more electronegative the atom accompanying hydrogen, the lower ...
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1answer
132 views

Tri-iodination of 2-methylpropane

In the reaction of tri-iodination of 2-methyl propane only five isomers can be formed, from which only the branch methyl can be iodinated if both the lateral carbond are iodinated .. Is this because ...
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1answer
2k views

Why do acetylene and chlorine react to yield carbon and HCl, but acetylene and bromine react less intensely?

In the famous "underwater fireworks" reaction we get $$\ce{C2H2 + Cl2 -> 2C + 2HCl}$$ On the other hand, when we react acetylene with bromine, we get $$\ce{CH#CH + Br2 -> CHBr=CHBr}$$ $$\ce{...
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1answer
684 views

Why is ICl5 unstable?

For the question Why is $\ce{ICl5}$ unstable? my textbook gave an answer of $\ce{ICl5}$ has too many highly electronegative chlorine atoms present on the central iodine. But how does having ...
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1answer
181 views

organic chemistry of alkyl halides and alcohols

What happens if a primary alcohol that also bears a halide substituent on the alcoholic carbon (the carbon to which the hydroxyl group is attached) when it is reacted with copper at 300 °C ? I ...
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0answers
128 views

Why is tin(IV) iodide bright orange while elemental iodine is violet? [duplicate]

Does it have anything to with iodines polarizability? Is there a way to explain this using sigma bonding or an MO diagram?
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1answer
871 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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2answers
1k views

Halogen and inductive effect

background : As proved by rate of EAS, mesomeric or simply conjugated resonance is weaker for halogens than inductive and make them electron taking, with fluorine almost doing nothing due to ...
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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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2answers
128 views

Reaction between 2 hydrogen halides

I know that hydrogen halides can react with each other to produce halogen halides. As an example here is a reaction between $\ce{HCl}$ and $\ce{HF}$: $$\ce{HCl + HF -> H2 + ClF}$$ As for the ...
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266 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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0answers
348 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
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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 ...
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1answer
2k views

Why does Iodine form Cations sometimes?

It is reported that iodine forms compounds like $\ce{(CH3COO)3I}$, $\ce{I(ClO4)3}$ and $\ce{IPO4}$ which contains $\ce{I+}$ and $\ce{I^3+}$ and are not bonded covalently as in interhalogen compounds. ...
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2answers
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How exactly does the reaction between alkyl halides and silver nitrite occur?

$$\ce{R-X + AgNO_2 -> RNO_2}$$ Now depending on the $\ce{R}$ and solvent the reaction can occur via $\mathrm{S_N1}$ or $\mathrm{S_N2}$. When the reaction proceeds via $\mathrm{S_N1}$ the product ...
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1answer
352 views

Why are alpha-carbonyl relatively less stable?

So if we have an alpha halogen ketone, why is an Sn1 type mechanism so unfavorable for that species? I don't understand. It seems like the C+ would be resonance stabilized by the carbonyl's double ...
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2answers
963 views

Grignards do transmetallation?

Grignards don't add to alkyl halides to create linear carbon extensions because Grignards do transmetallation rather than SN2 displacement of halide. Is this correct? I thought transmetallation a) ...
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1answer
555 views

Why does nucleophilic substitution of a haloalkane with ammonia produce ammonium, not a hydrogen halide?

For example, $\ce{CH3CHBrCH3}$ reacts with $\ce{:NH_3}$ to make $\ce{CH3CH(NH3^+)CH3 +:Br-}$,$$\ce{CH3CHBrCH3 \rightarrow CH3CH(NH3^+)CH3 +:Br-}$$then reacting again with $\ce{:NH_3}$ to make $\ce{...
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1answer
650 views

Basic and nucleophilic character of NaOH (aq)

Sodium Hydroxide (aq) is very effective in plucking off an acidic hydrogen. How effective will it be in substituting chlorine of an alkyl hallide (let us assume that the alkyl hallide is primary) and ...
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1answer
2k views

How would substitution reaction results differ between reacting halides with a tertiary bromoalkane vs reacting it with a primary bromoalkane?

Say, you conducted two separate reactions; in one, you combined $\mathrm{50~mmol}$ saturated $\ce{KCl}$ solution with $\mathrm{10~mmol}$ 1-bromooctane (assume heating), and in the other you combined $\...
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0answers
129 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 ...
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2answers
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How does SO2Cl2 react with alcohols?

Is the mechanism similar to the reaction of $\ce{SOCl2}$ with alcohols? If not, then how is it different? We have been taught about the latter at school but my friend quizzed me about $\ce{SO2Cl2}$. ...
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2answers
159 views

Comparision of boiling points

I was comparing boiling points of $\ce{CHCl_3}$ and $\ce{CH_3Cl}$. According to me B.P. of $\ce{CHCl_3}$ should be higher due to it's higher molecular mass than $\ce{CH_3Cl}$, but the answer is ...
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1answer
4k views

Why do halogen-metal exchanges happen?

I'm trying to understand organometallic raegents but am stuck at halogen-metal exchanges. For example if you have $\ce{PhBr + BuLi}$ you get $\ce{PhLi + BuBr}$, I don't understand why $\ce{PhBu + ...
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1answer
3k views

how to destroy excess iodomethane in reaction mixture?

I have used iodomethane to make a phenolic $\ce{OH}$ group to $\ce{OMe}$ group in Aq+Methanol medium. I have added water to precipitate the product of mine and will evaporate the solvents but I cant ...
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1answer
7k views

Why are the halogens good disinfectants?

I've been searching around the internet for a while and I know that Chlorine, Bromine and Iodine are used as disinfectants. My question is, what is the property of the halogens that make them ...
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0answers
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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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1answer
337 views

Preparation of 6-bromo-1-hexanol

I am refluxing $\ce{HBr}$ with 1,6-hexanediol for 16 hours at $80\ ^\circ\mathrm{C}$ in toluene. How can I be sure that more than $90\,\%$ of the product is brominated only at one terminal? If the ...
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2answers
959 views

Solubility of C5H11OH and C5H11Cl

Objectively, what makes the solubility of $\ce{C5H11OH}$ greater than the $\ce{C5H11Cl}$ in water?
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1answer
2k views

Orientation of halogenation

I was going through my chemistry book (RT Morrison and Boyd) and found a statement: " the collision frequency of isopropyl and n-propyl w.r.t. Chlorine atoms is the same." Is it correct because I ...
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1answer
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Which is the least stable trihalide of nitrogen?

Which is the least stable trihalide of nitrogen and why? I have two conflicting theories, one is that fluorine-fluorine electron repulsion will make $\ce{NF3}$ least stable and another is steric ...
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1answer
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Organic Chemistry - Nucleophilic Substitution Reactions

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
7k views

Why aryl halides are very less reactive towards nucleophilic substitution reactions? [duplicate]

I've often herd that aryl halides are very less reactive towards nucleophilic substitution reactions. One of the reasons for this I found was that there is resonance effect in the compound, but how is ...
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1answer
144 views

How to rationalise the difference in halogen bonding?

Can anyone explain the difference in halogen bonding to me. I understand the explanation in (c). It appears to me, that accepting that would contradict the answers to parts (a), (b), and (c). Is the ...
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2answers
730 views

Halogenation of an alpha-halogen ketone in acidic conditions

When a methyl ketone is submitted to halogenation in acidic conditions with two equivalents of a halogen, the first halogenation happens at the secondary alpha carbon atom , while the second ...
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1answer
588 views

Will I get bromine by electrolysis of the brine from the Dead Sea?

I know that electrolysis of a saturated solution of sodium chloride with an inert anode (eg., graphite) is a handy way to obtain pure chlorine. I have a sample of saturated salt solution from the Dead ...
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2answers
392 views

Formation of 2,4-Dichlorophenol by free chlorine mediated oxidation of Triclosan

I cannot find much guidance in the literature. This is the reaction between free chlorine in water and triclosan. I understand ether cleavage and electrophilic aromatic substitution (maybe) involved. ...
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2answers
4k views

How does chloroform degrade nitrile gloves?

Many of us have experienced the failure of nitrile gloves when exposed to chloroform. What's going on at a mechanistic level when this occurs? I would guess that the chloroform dissolves some of the ...
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1answer
15k views

Which silver halide is the most soluble?

Halides are group 7 elements. They generally have a low melting and boiling point. They are highly reactive. Silver chloride and silver bromide are not soluble in water. So they will be precipitates. ...