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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15
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2answers
630 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 ...
9
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0answers
190 views

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 ...
7
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0answers
194 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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0answers
1k 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 ...
7
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0answers
300 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 ...
6
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0answers
803 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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0answers
995 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 ...
6
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1answer
906 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
63 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 ...
5
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60 views

Can a per-acetylated sugar anomerize?

So I have a question concerning a reaction mechanism for the reaction below. I know for certain that I get the alfa anomer, but I can't explain it. When I draw out the mechanism it doesn't make sense ...
5
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0answers
2k 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 ...
5
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369 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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1answer
1k 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}...
4
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0answers
331 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
48 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 ...
4
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0answers
618 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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0answers
480 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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0answers
314 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 ...
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 ...
3
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0answers
376 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 ...
3
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683 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 ...
3
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0answers
54 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 ...
3
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4answers
8k 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{...
3
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0answers
65 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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42 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
859 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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0answers
106 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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0answers
59 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
52 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 ...
2
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0answers
160 views

Comparison of I-F, Br-F, and Cl-F bond strengths

From Chemistry of the Elements by Greenwood and Earnshaw [1, p. 833]: Figure 17.9 Mean bond energies of halogen fluorides. This shows the mean bond energy for $\ce{X-F}$, where $\ce{X}$ is a ...
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0answers
953 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 ...
2
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0answers
559 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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0answers
1k 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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0answers
90 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
64 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
89 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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24 views

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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0answers
49 views

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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62 views

When is a compound sterically hindered?

In a nucleophilic substitution reaction , which one of the following undergoes complete inversion of configuration ? (A) $\ce{C_6H_5CCH_3C_6H_5Br}$ (B) $\ce{C_6H_5CHCH_3Br}$ (C) $\ce{C_6H_5CHC_6H_5Br}$...
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0answers
53 views

Why London force dominates in Alkyl Halides

Why London Force is greater than dipole-dipole interactions in Alkyl Halides? As we know that most of the time London force is weaker than other forces. Then why in this case it's not so? ...
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0answers
224 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
244 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. $\ce{...
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0answers
59 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
505 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 ...
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0answers
218 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
75 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
352 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
118 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
140 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?...