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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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2answers
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Reactivity of primary and tertiary alkyl halides

From USNCO 2004, Q58: The reaction between which pair of reactants occurs the fastest for $[\ce{OH-}] = \pu{0.010 M}$? (A) $\ce{CH3CH2CH2CH2Cl + OH-}$ (B) $\ce{(CH3)3CCl + OH-}$ (C) $...
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0answers
29 views

What is the product when 1,4,6-trifluoroazulene is treated with sodium methoxide?

My logic During substitution via Path 1 and Path 2 aromatic intermediates are formed. Via path 3 anti aromatic intermediate is formed. Therefore reaction takes place via path 1 and path 2 only. ...
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0answers
39 views

Can vicinal di-iodide get eliminated by itself?

When $\ce{CH2I-CH=CH2}$ (2-iodoprop-1-ene) reacts with $\ce{HI}$ in aqueous solution, by Markovnikov addition, $\ce{CH2I-CHI-CH3}$ (1,2-diiodopropane) is formed. In the answer by aventurin here?, it ...
4
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1answer
38 views

Why is fluoride the most nucleophilic halide in aprotic solvents? [duplicate]

I am confused on the topic of electronegative nucleophiles, and polar aprotic solvents. From my understanding, the more electronegative a nucleophile is, the weaker of a nucleophile it will be, ...
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0answers
25 views

Alkyl halide addition [closed]

For the above question....i did the usual addition of HF across double bonds and joined both of them and.i thought the answer would be option(b) but the answer is something else please help!!
2
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0answers
53 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
32 views

Production of alkyl halides [duplicate]

One of the famous reactions of production of alkyl halides is the reaction of hydrogen halide with alcohols. The synthesis of the alkyl halide is different depending upon the halogens. I was taught ...
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2answers
110 views

Is fluorine sp3 hybridized in BF3

Since BF3 has the shape of tetrahedral, and in the provided solution, Boron is sp2, why is Fluorine sp3 hybridized?
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2answers
108 views

Does carbon monoiodide (CI) exist?

Many of my students get chlorine $\ce{Cl}$, confused with carbon monoiodide $\ce{CI}$, despite my promises to use serif fonts whenever possible and to never give them carbon monoiodide in a question. ...
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1answer
42 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 ...
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1answer
33 views

What is the configuration of dimethyl[tris(trifluoromethyl)]-λ⁵-phosphane?

I know that $\ce{(CH3)2P(CF3)3}$ is geometry of trigonal bipyramid and according to Bent's rule $\ce{CH3}$ goes to axial positions and $\ce{CF3}$s remains on equatorial positions. However, as per ...
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1answer
23 views

Can methyl halide be used in Wurtz reaction?

Yields of product(alkanes) are best for 1°(60%) and least for 3°(10%) alkyl halides. Can methyl halides be used in Wurtz reaction? Would it produce a good yield?
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1answer
85 views

Stability of 3d metal fluorides and iodides in different oxidation states

I read that the fluorides of 3d metals in lower oxidation states, e.g. $\ce{VF2}$, $\ce{TiF2}$, and $\ce{CuF}$ are thermodynamically unstable. For example, $\ce{CuF}$ disproportionates to $\ce{Cu + ...
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1answer
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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 ...
2
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1answer
393 views

What happens when (+) 2-iodobutane is treated with NaI in acetone?

After treating the compound with NaI, we should follow SN2 mechanism and the product will follow an optical inversion, giving us (-)2-iodobutane, but the answer is (±)2-iodobutane. After going ...
2
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2answers
88 views

Can vicinal dihalide produce conjugated alkene in strong base?

In Klein's Organic Chemistry (3rd edition), p. 410, we learn that vicinal dihalide can produce alkyne in strong base. And on Reaxys I see many reactions of this sort. For example: However, why isn't ...
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1answer
57 views

What's the difference between FFKM and PTFE?

These two fluorocarbon polymers seem to me very similar, the only difference I see is that FFKM is elastomer while PTFE aka Teflon is more of hard type of plastic. Isn't FFKM just PTFE with lower ...
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1answer
156 views

Wurtz Reaction with acidic alkyl halides [closed]

My chemistry book says we cannot use alkyl halides containing acidic hydrogen for Wurtz reaction. Why is this so?
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0answers
35 views

Why do amides react differently with PCl5? [duplicate]

In a reaction involving $\ce{PCl5}$ and any reactant containing oxygen atom, it generally takes out the oxygen and put chlorine their due to formation of strong bond between phosphorus and oxygen. ...
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0answers
38 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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1answer
164 views

What is the reaction of pentane-2,4-dione with chlorine in presence of NaOH? [duplicate]

We know that in haloform reaction alpha acidic hydrogen are substituted by halogen atom. But in the above case we find two acidic hydrogens in between the two keto groups (due to -R effect) which are ...
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0answers
54 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 ...
7
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1answer
66 views

If liquid hydrogen fluoride autoionises, how can it be an insulator?

According to Wikipedia, one of the last major hurdles in the isolation of elemental fluorine was the need to mix hydrogen fluoride with another substance in order for its electrolysis to be possible (...
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2answers
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Why does chlorination of toluene stop at two chlorine atoms?

My instructor mentioned a reaction for preparation of benzaldehyde by chlorination of toluene in presence of sunlight to form benzal dichloride, which on hydrolysis gives benzaldehyde. However, I'm ...
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0answers
176 views

Do alkyl halides get reduced with hydrogen/nickel catalyst?

According to my textbook, alkyl halides can't be reduced to alkanes by the $\ce{H2/Ni}$ or $\ce{H2/Pd}$ reducing agents, and almost no other reducing agents other than $\ce{LiAlH4}$ reduce alkyl ...
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1answer
120 views

Does chlorine trifluoride react with candlewax?

I've run across references to chlorine trifluoride quite a lot. It pops up fairly regularly on the Worldbuilding SE, and whatever idea people have with it is usually shot down very quickly - For ...
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0answers
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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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2answers
504 views

What are the functional group names of halogenoalkanes?

The functional group name of other organic compounds is easily findable, but that of the halogenoalkanes (or haloalkanes) is not. This makes me wonder if such a name exists for the halogenoalkanes or ...
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1answer
68 views

Does the van der Waals force not affect the alkali metal 's trend of decreasing melting points down the table? [duplicate]

Melting and boiling points increase further down the halogen group, but they decrease further down the alkali metal group. I know that the former's trend has to do with the van der Waals force, but I ...
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1answer
214 views

Are SN2 reactions in equilibrium?

I'm learning about SN2-reactions, and my text book gives the following examples of these reactions: $$\ce{HO^- +CH_3Br -> CH_3OH + Br^-}\tag{1}$$ $$\ce{I^- +CH_3Br -> CH_3I + Br^-}\tag{2}$$ ...
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0answers
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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 ...
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1answer
73 views

Monobromination of napthalene derivative

How does this reaction take place? Why does the bromine attach to that one particular location? I do know that since is $\ce{FeBr3}$ is present only 1 $\ce{Br}$ will attach non-substituted areas of ...
7
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2answers
356 views

Determine minimum C-H bond length in ethane derivatives

Which of the following compound has minimum C-H bond length? ethane ethene 1,2-dibromoethene 1,2-dibromoethane How can we know the comparison of $\ce{C-H}$ bond length (not $\ce{C-C}$...
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122 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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2answers
407 views

Reactivity of meta- and para-bromo-nitrobenzene towards nucleophilic substitution

Among 1-bromo-3-nitrobenzene and 1-bromo-4-nitrobenzene, which would be more reactive towards nucleophilic substitution? From what I can infer, the answer should have been 1-bromo-3-nitrobenzene. ...
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0answers
272 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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1answer
572 views

What are the products of the reaction of methoxypropane with HBr?

The products of the reaction of methoxypropane ($\ce{CH3CH2CH2OCH3}$) with $\ce{HBr}$ are? In my opinion, the products should be: bromopropane ($\ce{CH3CH2CH2Br}$) + methanol ($\ce{CH3OH}$). The ...
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4answers
476 views

Why is fluorine the best oxidising agent, but also the most basic?

(Please note that all comparisons I have made below are with respect to halide ions only.) According to what I have learnt, the fluoride ion is the most basic ion, because it has the smallest size ...
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0answers
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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 ...
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1answer
84 views

What are the products formed when phenol is reacted with benzyl bromide? [closed]

What are the products formed when phenol is reacted with $\ce{PhCH_2Br}$ (benzyl bromide)? I can think of two ways in which the reaction would proceed. One would be the formation of an ether through ...
12
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1answer
358 views

Why does a six-membered ring contract in this SN1 reaction?

I was watching this video on Khan Academy (YouTube link) regarding SN1 mechanisms and carbocation rearrangements and came across this mechanism. At around timestamp 4:20 in the video, why does step 2 ...
3
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1answer
437 views

How to calculate the percentage yield for enantiomers in free radical halogenation?

How many mono-chlorinated products of 2-methyl butane will be formed upon chlorination in the presence of sunlight? Find the percentage of major product formed. Six products were formed: two ...
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0answers
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Why do halohydrins in base react to give epoxides rather than a substitution or elimination reaction?

The halohydrin reaction in base is well known for making epoxides. However I am confused as to why the base does not simply perform SN2 on the bromine atom, or an E1 on an adjacent carbon atom.
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1answer
533 views

Reaction of dihalides with excess of NaNH2

Gem-dihalides react with $\ce{NaNH2}$ to give terminal alkynes. Why is a terminal alkyne prefered? For example, I had thought that 2-pentyne would be preferred over 1-pentyne as it would be more ...
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1answer
273 views

Can alkyl fluorides be formed by the Hunsdiecker reaction?

We know that the Hunsdiecker reaction is $$\ce{RCOOAg + X2 ->[CCl4] RX + AgX + CO2}.$$ This reaction is successful with chlorine and bromine. Also, we know that if $\ce{X}$ is iodine, we will get ...
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4answers
86 views

Chlorinating specifically one carbon on a symmetrical alcohol

The final target molecule is 1-chloro-2-amino propane. The amination step would be simple via reductive amination of 1-chloro-iso-propanone. Obtaining 1-chloro-iso-propanone would be from ...
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0answers
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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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1answer
239 views

Mechanism of lithium-halogen exchange of primary alkyl iodide

On Clayden's page 190 this reaction is given for preparation of organometallics: What is the mechanism of this reaction? I expected the "almost carboanion" part of the $\ce{t-BuLi}$ to attack as a ...
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1answer
102 views

Why does DMSO help facilitate halohydrin reactions?

It would make sense, due to bond energy, that water molecules would have a hard time competing with $\ce{Br}$ in a bromonium ion intermediate. However, I was reading that by doing the reaction in ...
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0answers
127 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 ...