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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
384 views

Product of the addition of 1 eq. bromine to 1-methylcyclohexa-1,4-diene

When we add one equivalent of $\ce{Br2}$ then which double bond will get brominated? The double bond in the molecule with methyl group will be more stable as it will have more hyper conjugating ...
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0answers
41 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
52 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
519 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 ...
3
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2answers
3k views

Does isopropyl chloride undergo SN1 or SN2 with sodium acetate?

What's the reaction of isopropyl chloride with sodium acetate? (The solvent is acetic acid) Is it SN1 or SN2? My thoughts: It's not that difficult to approach isopropyl chloride's carbon, for there ...
2
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1answer
787 views

SN1, SN2 or acid-base reaction

I am asked to give the type of reaction (SN1, SN2 or acid-base reaction) for the following reactions. I know that both $\ce{MeOH}$ and $\ce{EtOH}$ polar protic solvents, so because the first is an SN2 ...
3
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1answer
2k views

Which of the following statements is true about the trend down group 7?

Which of the following statements is true about the trend down group 7 (halogens) with increase in atomic number? The reactivity increases. The atoms get smaller The boiling points ...
7
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1answer
7k views

Why does color of halogen deepens and the boiling point decreases down the group?

Why does the color of the halogens deepens as we go down the group? also why there is a change in physical state of halogens down the group? \begin{array}{c|c} \mathbf{Gas} & \mathbf{Color} \\\...
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2answers
2k 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. ...
6
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1answer
125 views

Is it possible for the iodine atom in periodate ester to be octavalent?

Recently, I was reading Clayden's Organic Chemistry (2nd ed.) and I chanced upon this diagram on p. 443 (as shown below) showing an octavalent iodine in the periodate ester. I found this rather ...
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0answers
151 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 ...
2
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1answer
599 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
333 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 ...
6
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3answers
2k views

What will be the major product of of the Wurtz reaction of 3,6-dibromocyclohexa-1,4-diene?

According to me, the answer should be (A) because that's a Wurtz reaction, but the answer given in the book is (B).
4
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1answer
6k views

What product is formed in the Wurtz reaction of 1-bromo-3-chlorocyclobutane?

I want to do Wurtz reaction of 1-bromo-3-chlorocyclobutane: Wikipedia suggests to do an intramolecular reaction. Instead, I remember reading somewhere that bromine is more reactive and hence we ...
3
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1answer
415 views

Why does this E2 reaction occur on the less substituted carbon?

In compound C it eliminates the beta hydrogen attached to the less substituted carbon, rather than attacking the beta hydrogen attached to the tertiary carbon. Why is this the case?
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2answers
3k views

What are the products of the hydrolysis of ICl3?

I have learnt that interhalogens on hydrolysis give a halic acid derived from the smaller atom and an oxoacid derived from the larger atom. For example hydrolysis of $\ce{BrF5}$ would give me $\ce{HF}$...
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1answer
625 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 ...
5
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1answer
5k views

Why do we need to add FeBr3 for bromination of anisole, but not for bromination of phenol?

I understand that we need to add $\ce{FeBr3}$ while brominating benzene in order to polarize the bromine molecule. However, we do not need to add such a Lewis Acid in the case of phenol, because it is ...
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2answers
1k 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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2answers
4k views

Is carbon tetrachloride an electrolyte?

Is $\ce{CCl_4}$ an electrolyte all by itself, or does something need to be added to it so that it becomes an electrolyte? Also, is it weak or strong?
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1answer
139 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 ...
4
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1answer
1k views

Why is only bromine used in the degradation reaction?

Why specifically is bromine used in the degradation reaction (Hoffmann bromamide)? Why can't the same be performed using chlorine or iodine? In other words, what makes bromine a more convenient ...
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4answers
3k views

What are the products of the reaction between fluorine and ammonia?

What are the products of the reaction between fluorine and ammonia? Is it the same as with chlorine and ammonia, which depend upon which reactant is taken in excess?
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1answer
6k views

Why does F replace the axial bond in PCl5?

Why does $\ce{F}$ replace an axial bond in $\ce{PCl5}$? I realize that it would be more stable there than at equatorial bond, but what is the reason of its stability? Similarly in $\ce{AB4}$ type of ...
7
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2answers
2k 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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1answer
329 views

What does the molecular orbital scheme of beryllium chloride and hydride look like?

Beryllium is a somewhat fascinating element since it is the only member of the second group that behaves somewhat non-metalish and, e.g. forms a somewhat covalent chloride and a covalent hydride. In ...
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2answers
9k views

Why does tetrachloromethane have a higher boiling point than trichloromethane?

London dispersion forces (LDF) are present in all molecules, whether polar or non-polar. Molecules also exhibiting dipole-dipole interactions (in addition to the LDF) must have stronger forces of ...
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4answers
2k 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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1answer
2k 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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1answer
304 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
634 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
863 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 ...
2
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1answer
2k 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 ...
3
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4answers
136 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 ...
3
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1answer
260 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
138 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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2answers
13k views

Why is allyl chloride more reactive towards substitution than alkyl chloride?

I can understand that the reactivity of alkyl halide is more than vinyl and aryl halides because the halogen atom in alkyl halide is connected to the sp3 carbon. Whereas in vinyl or aryl the halogen ...
4
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0answers
267 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
votes
1answer
219 views

Reaction of alkyl bromide in presence of piperidine

What are the products of this reaction? I believe there'll be E2 elimination to give the products. Not sure. Help would be greatly appreciated. The above is the product which I thought might be ...
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1answer
2k views

Which chlorine species can act as an oxidizing agent but not as a reducing agent?

Which species can act as an oxidizing agent but not as a reducing agent? (A) $\ce{Cl2}$ (B) $\ce{Cl-}$ (C) $\ce{ClO2-}$ (D) $\ce{ClO4-}$ I thought the answer was A because if $\ce{Cl}$ ...
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0answers
143 views

Mechanism for the formation of an alkyl halide from alcohol and phosphorus trihalide [duplicate]

I was reading about synthesis of alkyl halides from $\ce{PX3}$. I want to know the mechanism for this reaction. According to Solomons and Fryhle, no rearrangement takes place in case of $\ce{PBr3}$ , ...
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 ...
3
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2answers
10k views

Structure of xenon hexafluoride

The central atom has a hybridization of $\mathrm{sp^3d^3}$. Thus, its structure should be pentagonal bipyramidal. Why is it not that but a distorted octahedron?
4
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1answer
8k views

Why is fluorine more reactive than iodine despite the weaker I-I bond?

The atomic radius of halogens increases as we go down the group due to the addition of new shells. As a result, the bond length of halogen $\ce{X-X}$ increases down the group. So, less energy is ...
7
votes
1answer
254 views

Mechanism for the conversion of an unsaturated alkyl halide to an alcohol

Question: Predict the mechanism for the following reaction: Attempt: I thought it will proceed through SN1 mechanism as $\ce{H_2O}$ is involved (solvolysis). So I proceeded with the ...
5
votes
1answer
659 views

Addition reaction of hydroiodic acid to 2-bromo-3-chloro-2-butene

How can the major product of the addition reaction of 2-bromo-3-chloro-2-butene with hydroiodic acid be predicted, since Markovnikov's rule fails to distinguish it? $$\ce{H3C-C(Cl)=C(Br)-CH3~+~HI~-&...
12
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2answers
2k views

Bromination of 1,3,5-cyclooctatriene followed by nucleophilic substitution by excess dimethylamine

Write the mechanism for the following reaction (bromination of 1,3,5-cyclooctatriene followed by nucleophilic substitution by excess dimethylamine): My answer so far: I have only shown one of ...
19
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2answers
247 views

What happens chemically to 5'-radiolabeled aqueous thyroxine (thyroid prohormone) when its I-131 undergoes beta+gamma decay?

Related to this question about $\ce{^{14}C}$ beta decay in $\ce{CO2}$, what happens when the $\ce{^{131}I}$ in radiolabeled thyroxine (thyroid prohormone, or "T$_4$") undergoes beta-plus-gamma decay ...
5
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2answers
1k views

Why does rearrangement not take place in Wurtz reaction?

The Wurtz reaction is $$\ce{R-X + Na ->[ether] R-R}$$ where $\ce{R}$ is alkyl. But if we take butylchloride with $\ce{Na}$, the product is n-octane and not 3,4-dimethylhexane. I am unable to ...