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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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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238 views

Convert hexane to 1,6-dibromohexane

Is it possible by any means or by using some reagents to convert hexane to 1,6-dibromohexane? The yield should also be good.
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What are the conditions for making amines from alkyl halides?

From what I understand, to make an amine from an alkyl halide you need to heat the alkyl halide with a mixture of ammonia and ethanol. I have two questions: Do both ammonia and ethanol need to be ...
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4answers
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Conversion of propane to methane [closed]

I had a question in my textbook to convert propane to methane. The basic idea was chlorination in presence of sunlight. However, two products are obtained in this case - namely 2-chloropropane and 1-...
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1answer
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The role of halogens in electrophilic aromatic substitution

I'm trying to understand what halogens do in electrophilic aromatic substitution. Consider the following. Bromobenzene is introduced to a carbocation. Bromobenzene will likely react, but at a slower ...
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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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1answer
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Hydrolysis products of chlorides of group 15

$\ce{NCl3}$ on hydrolysis produces $\ce{NH4OH}$ and $\ce{HOCl}$. $\ce{PCl_3}$ when hydrolyzed produces $\ce{P(OH)3}$ i.e. $\ce{H3PO3}$. $\ce{AsCl_3}$ when hydrolyzed produces $\ce{As(OH)3}$. ...
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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 ...
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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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759 views

Reaction of conjugated alkene with KNH2

I could not think of this reaction fitting into any of the reactions I know except the aryne mechanism. And hence I came up with the following mechanism after seeing the answer (which I've written in ...
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Why is the boiling point of alkyl iodide is more than alkyl fluoride?

As far as I know, more the polar character of the organic compound, more will be the energy required to break the bond and thus more boiling temperature. Here in this case, $\ce{R-F}$ is more polar in ...
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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? ...
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Will this beta-branched secondary alkyl halide undergo SN1 or SN2?

What is the correct mechanism here? Would SN1 occur here? I chose SN2 because we have a secondary alkyl halide with a weak base $\ce{CN-}$. However, the solution says SN1 is major. Can you explain ...
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Why is thionyl chloride preferred for preparing alkyl chlorides from alcohols?

Why is thionyl chloride ($\ce{SOCl2}$) preferred for preparing alkyl chlorides from alcohols, as opposed to say $\ce{PCl5}$ or $\ce{PCl3}$ ?
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Is a carbon-fluorine bond stronger than a carbon-chlorine bond?

In hydrolysis/nucleophilic substitution of haloalkanes, the bond enthalpy indicates the rate of hydrolysis (e.g. the $\ce {C-I}$ bond is weaker than the $\ce {C-Cl}$ bond so in hydrolysis the alkane ...
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1answer
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Is the bond dissociation enthalpy of Cl-F greater than that of Cl-Cl?

In my book, it is mentioned that $\ce{Cl-F}$ has greater bond dissociation enthalpy than $\ce{Cl-Cl}$. Is it true? I know that interhalogen molecules usually have weaker bonds than dihalogen molecules ...
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Major product monochlorination of 2-methylpropane [duplicate]

What is the major product of monochlorination of 2-methylpropane and for 2-methylbutane? My attempt: as in 3 degree position, monochlorination is favoured (due to free radical formation), so ...
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1answer
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How can aqueous KOH give alcohol by SN2 of alkyl halide?

I ask this because SN2 requires a strong nucleophile, and I have read $\ce{OH-}$ isn't a strong nucleophile in a polar protic solvent like water. So, how can $\ce{OH-}$ replace, say $\ce{I-}$ from $\...
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Relative acidity of p-chlorobenzoic acid and p-flurobenzoic acid

I want to compare the relative acidity of p-chlorobenzoic acid and p-flurobenzoic acid. Both of the facts below point to p-chlorobenzoic acid being more acidic: The carboxylic acid group is too far ...
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2answers
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Deciding E1/E2/SN1/SN2 for cyanide ion

The $K_\mathrm{a}$ for $\ce{HCN}$ is $6.17 \cdot 10^{-10}$ with a $\mathrm{p}K_\mathrm{a}$ of $9.21$ Thus, the cyanide ion is a strong base. Also, the cyanide ion is a good nucleophile. So in the ...
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1answer
906 views

Identifying covalent character in ionic compounds when varying multiple ions

By Fajans' rules, we can easily find out which compound shows covalent character. Example: Among $\ce{NaCl}$, $\ce{MgCl2}$, $\ce{AlCl3}$ which one is more covalent? Answer: There is a point in ...
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How do quaternary ammonium salts catalyse SN2 reactions?

I am asked to identify the "best catalyst" for the reaction: $$\ce{CH3(CH2)8CH2Br->[\ce{KCN}][\text{benzene}]CH3(CH2)8CH2CN}$$ The options are (A) benzyl chloride (B) aniline (C) N,N,N-...
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Why is the reactivity of primary alkyl halides with nucleophiles (SN2 mechanism) greater than secondary and tertiary alkyl halides?

For the reaction between alkyl halide and a nucleophile, following the SN2 mechanism, the reactivity of alkyl halides is in the order: primary halide > secondary halide > tertiary halide. If you ...
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1answer
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How can a methyl halide react by intramolecular SN2?

Out of the following, $\ce{CH3Br}$ doesn't react by which mechanism? SN2 SN1 E2 Intramolecular SN2 E1 My textbook gives 2, 3 and 5 as the correct answers, which means it does react ...
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445 views

Why is the effect of beta-branching neglected in this comparison of SN2 reaction rates?

Which compound would give a faster SN2 reaction? 2-bromobutane 1-bromo-2-methylpropane The answer is given (2). While I agree that the primary position is preferred as compared to the ...
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1answer
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Use of aqueous KOH and alcoholic KOH in dehydrohalogenation reactions [duplicate]

What is the difference between aqueous KOH and alcoholic KOH? How do they react differently in dehydrohalogenation?
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1answer
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Is an SN1 reaction possible in halobenzene?

Is an SN1 reaction possible in halobenzene? Will the phenyl carbocation be stabilized via resonance? Suppose the leaving group is very electronegative and the environment is protic. What then would ...
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Dehalogenation of vicinal dihalides

Why, among different metals, only zinc is favourable for the dehalogenation of vicinal dihalides?
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639 views

Why doesn't the bromide anion attack during electrophilic addition of bromine in methanol solvent?

It is known that addition of bromine (in methanol) to ethene will yield 1-bromo-2-methoxyethane. The reaction proceeds with the formation of a bromonium intermediate in the first step. In the second ...
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Origin of alkenes from Wurtz Reaction

According to Wikipedia: Also, since the reaction involves free radical species, a side reaction occurs to produce an alkene. This side-reaction becomes more significant when the alkyl halides are ...
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Why is WF6 stable whereas CrF6 is unknown?

$\ce{F-}$ is a hard base since it is small and relatively polarizable. Both $\ce{Cr^6+}$ and $\ce{W^6+}$ are hard acids, but shouldn't $\ce{CrF6}$ be favored since it would be a smaller hard acid?
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Relative importance of electronegativity and bond length for dipole moment magnitude

In this answer to the question "Why is the dipole moment of chloromethane larger than the dipole moment of fluoromethane?", the order of the dipole moments was given as $\ce{CH3Cl > CH3F > CH3Br ...
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Why is the dipole moment of chloromethane larger than the dipole moment of fluoromethane?

On the Pauling electronegativity scale, fluorine and chlorine are 3.98 and 3.16, respectively. Since the dipole moment is dependent on electronegativity, why is the dipole moment of chloromethane ...
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Why does chlorine undergo disproportionation in alkaline media?

One reaction used to form sodium hypochlorite (A type of bleach) is as follows: $\ce{2NaOH(aq) +Cl2(g)->NaOCl(aq) + NaCl(aq) + H2O(l)}$ Provided the sodium hydroxide is dissolved in some ...
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1answer
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Reaction of an alkyl halide with silver nitrite

I want to know that whether both alkyl nitrite and nito alkane are produced or if nitroalkane is the only product. There are many different (contradicting) things written in different books that is ...
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1answer
239 views

How to test for halides without ammoniacal silver nitrate solution? [closed]

If I have an halide e.g magnesium iodide, how can I test what halide the compound contains? I understand there is a method using silver nitrate and ammonia but what other methods are there?
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Elimination reaction of 1-bromo-2-phenylcyclopentane

In the following reaction, treating the trans-1-bromo-2-phenylcyclopentane with ethanolic KOH gives an alkene. But in this case, the double bond is on the left side (less substituted) instead of being ...
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Major product formed when 1,1,1-trichloropropane is treated with aqueous KOH

What are (is) the product formed when 1,1,1-trichloropropane is treated with aqueous potassium hydroxide? I think the major product should be propionic acid, but I'm not sure.
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What is the net ionic equation for rection of liquid bromide with sodium iodide crystals?

I have this problem, Liquid bromine is added to a container of sodium iodide crystals I interpreted it with this molecular formula $\ce{Br_{2(l)} + 2NaI_{(s)} \rightarrow 2NaBr_{(s)} + I_{2(g)}}$. ...
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1answer
241 views

Reaction of 1-(1-chloroethyl)-1-methylcyclobutane under E1 Conditions

What is the major product of the following reaction? $\hspace{40 mm}$ $\hspace{20 mm}$ It looks to me that the $\ce{Cl}$ group leaves then there's an alkyl shift to where the $\ce{Cl}$ ...
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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 ...
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Why does free-radical chlorination of isopropyl bromide give 1-bromo-2-chloropropane? [closed]

Source: Morrison and Boyd - Chapter Alkanes - exercise no. 15 Free-radical chlorination of either n-propyl or isopropyl bromide gives 1-bromo-2-chloropropane, and free-radical chlorination of ...
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Rates of hydrolysis in bicyclic and monocyclic compounds

Which of the following compounds, 1-bromo-1-methylcyclohexane 1 or 1-bromobicyclo[2.2.2]octane 2, hydrolyzes faster (under comparable conditions)? It may be acid catalyzed or base catalyzed hydrolysis,...
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1answer
578 views

Hydrolysis of vinyl bromide vs alkyl chloride

Which of the following compounds, 1-bromocyclopent-1-ene 1 or chlorocyclopentane 2, hydrolyses faster than the second under comparable conditions? It may be acid catalysed or base catalyzed hydrolysis ...
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1answer
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Inability of alkyl fluorides to be reduced to an alkane in the following reaction

Alkyl halides except fluorides on reduction with $\ce{Zn}$ and dil. $\ce{HCl}$ gives alkane. Example: $$\ce{CH3Cl + H2 -> CH4 + HCl}$$ Why cannot alkyl fluorides be reduced?
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Bromination of cyclohexene

Cyclohexene is reacted with bromine in carbon tetrachloride in the dark. The product of the reaction is: I know that reaction with bromine in $\ce{CCl4}$ will result in vicinal ...
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Why can't primary alcohols react with sodium bromide via an SN2 mechanism?

I was told that a primary alcohol reacts with $\ce{HBr}$ for example, but not with $\ce{NaBr}$ through the $\mathrm{S_N2}$ mechanism in the same reaction environment. Why? This reaction can occur: $$...
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1answer
803 views

What results from the reaction of 5-bromopentan-1-ol and NaOH?

In our chemistry class, we noted three molecules that result from the reaction: pentane-(1,5)-diol This one is simple to understand, simply a nucleophilic substitution between $\ce{Br^-}$ and $\ce{...
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715 views

How to get (2R,3R)-2,3-dibromobutane from but-2-yne?

What I had in mind was to form but-2-ene with $\ce{H2}$ and Lindlar's catalyst and then simply add bromine ($\ce{Br2}$). But this addition, if I'm not mistaken, is a trans-addition. So I would end up ...
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522 views

In Finkelstein reaction, how does precipitate formation favor forward reaction? [duplicate]

In my textbook it's stated that: $\ce{NaCl}$ and $\ce{NaBr}$ thus formed is precipitated in dry acetone. It facilitates the forward reaction according to Le Chatelier's principle. Is this related ...