Questions tagged [reaction-mechanism]

The detailed (and as complete as possible) description of plausible or observable pathways leading from reactants to products of a chemical process. This tag should be applied to questions about these processes. It may be applied to hypothetical and/or proposed mechanisms.

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Formation of compounds and lewis structure

I want to know whether its correct that the Lewis structure represent the most likely compound structure to be formed according to the octect rule? I see that if you take Nitrogen which has 5 valence ...
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Why 9BBN's rings don't migrate during hydroboration-oxidation?

My organic chemistry textbook (Clayden, Warren, Greeves) says this: If we use the $\ce{HBR2}$ reagent $\ce{9-BBN}$, then only the non-cyclic substituent formed in the hydroboration reaction will ...
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What will be the product of reaction of aniline with chromic acid?

I was trying to figure out what will be the the product on reaction of aniline with chromic acid. Answer: I know that $\ce{-NH2}$ will be protonated in acidic medium but I am unable to understand ...
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What Mechanism is followed when alcohols are reacted with sodium Bromide, Sulphuric acid

$\ce{R-OH + NaBr + H2SO4->R-Br + NaHSO4 + H2O}$ Due to sulphuric acid, the ${\ce-OH}$ group will get protonated and convert into $\ce{-H2O+}$ which is a great leaving group in comparison to the ...
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Why lactols being tetrahedral complexes do not break?

The answer given is (D) but I think (B) should be the answer as the concerned benzylic carbon in option (D) is an unstable tetrahedral complex and it should break. Besides, the medium is acidic so it ...
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Decide major product for first order elimination reaction

This is my own question which may come in intermediate step of aldol condensation in acidic medium (but I don't got a molecule whose aldol condensation represent my doubt exactly). Information is ...
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Evaluating inductive effects in cyclic compounds

I was required to find the products on heating the hydroxide of; Now it's easy enough to find the answer; Hoffman elimination isn't going to happen from the methyl, and the n-propyl doesn't have $\...
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Meta-directing nature of anilinium cations

The comments on this answer seem to detail a trend in which $\ce{NR3+, NHR2+, NH2R+}$ all show meta-directing nature towards electrophilic substitution, with the slightly stronger para-direction of $\...
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Is considering HVO3 + n ROH = HVO3(ROH)n as an endothermic reaction logical?

Here is an article on vanadium solvent extraction with 2-ethyl-1-hexanol: Separation and Purification Technology 2017, 188, 358-366 The suggested extraction reaction is HVO3 + n ROH = HVO3(ROH)n, ...
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Radical Chain Reaction, termination steps

In the termination step of radical chain reaction, we often neglect the recombination of hydrogen atom radicals and it will not be included in the mechanism. Let say the reaction is between $\ce{H2}$ ...
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Why do resorcinol and iodine react to give 2-iodobenzen-1,3-diol?

I am supposed to perform the above shown reaction in the lab soon, but I don't really understand the mechanism behind it. I got told by my lab assistant that the mechanism is an electrophilic aromatic ...
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Cyanide hydrolysis; could it yield an oxime?

The mechanisms for both acid and base catalyzed hydrolysis of nitriles are clear; (With the subsequent deprotonation from the hydroxyl) and (Source) In both cases, the hydroxyl adds to the carbon ...
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Yield of alkyl chloride in the Hunsdiecker reaction

Apparently the yield of alkyl chlorides is low as compared to that of alkyl bromides when preparing alkyl halides using the Hunsdiecker reaction. Why does this occur? The only factor I can see is the ...
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Why are we not getting the most stable product in Aldol condensation?

The picture above is from my class notes. I am familiar with the mechanism of both acid and base catalysed Aldol condensation. I also understand the reason why KCP was told as the major product in ...
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Proton removal during benzyne formation in substituted haloarenes

I encountered the following question in an organic chemistry paper - The reaction follows benzyne mechanism. My answer was B. However, the answer given in the test solutions was D. The mechanism ...
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Regarding Hard and Soft nucleophiles

In the above reaction, I was told that the reason organocadmium reacts only with aryl chloride segment is because it is very less reactive and reacts only with most reactive sites. This was consistent ...
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Why negative charge delocalises away from electronegative atoms

In the mechanism for the Wolff-Kishner reduction, after the $\ce{OH-}$ abstracts a proton, the resulting negative charge delocalises away from the nitrogen atom to the carbon, and the subsequent ...
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Is Chromium (VI) fluoride possible?

Chromium (VI) fluoride, also known as chromium hexafluoride is a possible chemical compound with a chromium atom attached to 6 fluorine atoms. It has been unsuccessfully synthesized a number of times ...
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Products of the reaction between ethoxyethene and HI

Problem The products formed in the reaction $$\ce{CH2=CHOCH2CH3 + HI ->}$$ are (a) $\ce{CH2=CHI}$ and $\ce{CH3CH2I}$ (b) $\ce{CH2=CHI}$ and $\ce{CH3CH2OH}$ (c) $\ce{CH3CHO}$ and $\ce{CH3CH2I}$ (d) ...
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On the molybdenum(III) oxide-catalysed oxidation of alkanes to carbonyls

The following reaction is specified in my notes; $$\ce{CH4 ->[Mo2O3, \Delta]HCHO}$$ The intermediate steps involve the dehydration of an alcohol to yield the final product. Wouldn't this only work ...
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Manganese(IV) oxide oxidation of carbocations

As I understand it, $\ce{MnO2}$ selectively oxidises benzylic and allylic alcohols to carbonyls. But this also works for making alcohols out of carbocations, apparently. I found the following ...
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Mechanism of formaldehyde / phenol condensation

The production of bakelite using this method, but with an acid as the catalyst is simple enough; a protonation of the carbonyl oxygen, followed by an electrophilic substitution to the ring. The ...
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Stability of radical ions [closed]

Which will be more stable- Radical anion or Radical cation. This is in context to Tollen's Test Mechanism. I think that the radical anion would be more stable due to resonance; however, there may also ...
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list of chemical kinetics software [closed]

Is there a list available for free chemical kinetics/chemical reaction software (that preferably can model combustion)? I've searched but I can't find anything.
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First step in a reaction between an acyl chloride and sodium acetate in acetic acid

What would the first step be in a reaction between acyl chloride and sodium acetate in the presence of acetic acid? I'm a bit confused because I'm not quite sure which step would occur first. I was ...
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On which side is the intermediate carbocation formed during acid-catalyzed opening of epoxide?

I found an organic chemistry question which asked the major product of the following reaction - The mechanism for the same in the answer was - My questions regarding this are as follows - The ...
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Periodic acid oxidation of carbonyls?

The following reaction seem to be valid; $\ce{CH2OH-CHOH-CH2OH ->[HIO4]CH2O + HCOOH + CH2O + 2H2O}$ Apparently, there are similar reactions by 2,3-dihydroxypropanal, and also by the straight chain ...
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Lindemann-HInshelwood mechanism difference between high and low concentration

I have a gas reaction which follows the Lindemann-Hinshelwood mechanism and want to calculate the rate constant at low and at high concentrations of the gas but I find myself stuck at what my next ...
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What is the reaction mechanism between boric acid and 2-ethyl-1-hexanol

Here is a photo from an article, Hydrometallurgy 2016, 160, 129–136 This indicates the reaction mechanism as esterification. However, the written reaction equation ($\ce{H3BO3 + nROH -> H3BO3.nROH}...
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Which oxygen is favored for protonation when hydrolysis of an acetal occurs?

My question is about which oxygen is favored for protonation in acidic conditions. So, R1 and R2 are different in the following diagram (for example, one is propyl but the other is ethyl). I looked up ...
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Why does (2-methoxyethyl)benzene undergo nitration at the ortho position (major product)?

This is an option in a question in which we needed to mark all the correct reactions: According to the answer key, this is a correct option. As an alkyl group is directly bounded to the benzene ring, ...
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On the use of hexane in the organic reduction by DIBAL-H

In some variations of the organic reduction by DIBAL-H, I've seen hexane used, as in this equation from this website; I've looked it up, but I haven't seen any explanation for why hexane's used there....
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What reagents are used to selectively reduce 2,2,3‐trimethyloxirane to secondary and tertiary alcohols?

Problem Answer Questions I know $\ce {LiAlH4}$ is a reducing agent because it gives four $\ce{H-}$ and will attack on our reactant on carbon with less substituents, i.e. in this case on $\ce{-CH-}$ ...
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On the relative ease of E2 dehydration

Concerning alcohol dehydration, I get that it's E1 in secondary and tertiary alcohols, that it's E2 in primary alcohols, and also why E1 reaction is easier for tertiary alcohols as compared to ...
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Calculate equilibrium constant from Arrhenius [closed]

Is there a way to calculate the equilibrium constant from the Arrhenius equation. Say, I am given that A = $4.21 *10^{-13} s^{-1}$ and $E_a = 99.0$ kJ/mol for a Lindemann-Hinshelwood gas reaction. How ...
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Lindemann–Hinshelwood mechanism for a gas reaction

The effective rate constant for a gaseous reaction which proceeds by a Lindemann–Hinshelwood mechanism is $\pu{1.01E-5 s^-1}$ at a concentration of $\pu{4.6E-6 M}$ and $\pu{2.21E-5 s^-1}$ at a ...
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Difference between Tishchenko reaction and Meerwein-Ponndorf-Verley reduction

For the Tishchenko reaction, Al(OEt)3 is used as reagent where an aldehyde is oxidized as well as reduced, so it's a redox reaction. Whereas in Meerwein-Ponndorf-Verley reduction, an aldehyde is ...
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What is the literature value of the activation energy of the reaction between iodate and bisulfite?

I explored the Arrhenius equation using the reaction between potassium iodate (containing the IO3- iodate ion) and sodium metabisulfite (bisulfite ion), however I can't find a literature value to draw ...
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Acid catalyst decarboxylation of 1-carboxyl-tryptoline

One of my labs had the following reaction: I understand the Pictet Spengler mechanism. However, I am confused about the decarboxylation. I cannot come up with a way in which this decarboxylation ...
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Why does citrulline have two pka values?

Can someone explain to me why citrulline has two pka values? It has a carboxy group that could donate a proton, but where would the second proton come from? Should the amide group not be more basic ...
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How is this Cope Reaction forming Ethene as major product?

I have been asked to find the major product of the reaction: As this a case of pyrolysis of $3^{\circ}$ Amine Oxide (or, in other words, Cope Reaction), I figured there are two possible products ...
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Determine reaction order and reaction rate

In a solution of $\ce{Fe^3+}$ the concentration was measured to be: $$\begin{array}{c|c} t/\pu{min} & \ce{[Fe^3+]}/\pu{\mu M} \\ \hline 10\ & 238\\ 20 & 227\\ 40\ & 206\\ 60\ & ...
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Stabilization of multiple bonds through inductive effects

In the conversion of m-chloroanisole to m-anisidine using $\ce{NaNH2}$ and liquid $\ce{NH3}$, apparently the reason the $\ce{NH2-}$ goes for the meta- position instead of the para position is that, in ...
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How can i remove rust from tinplate without damaging further the paint?

Some of my steelbooks, made of tinplate, as far i know, is starting to rust, how can i remove that rust without damaging the surronding paint? In case there is any option, should I apply only to the ...
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Where do I find data on 'molecular membership' sequences?

Techniques such as isotopic labeling allow for radioactive tracing of an element through a sequence of molecules. Using analytical instruments (such as LC-MS) we can then find out where labelled atoms ...
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1answer
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How is the hydrazone formed in the Wolff-Kishner reduction?

In the Wolff-Kishner reduction the first step is to react a carbonyl with hydrazine to form a hydrazone. The later steps of the reaction requires a strong base to cause loss of nitrogen. However, the ...
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1answer
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Mechanism of hydrolysis of acyl chlorides

The following mechanism for acyl chloride hydrolysis was given by my professor : However I do not understand why in the second step, oxygen has a partially negative charge, should it not gain a ...
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57 views

Reaction of Copper and concentrated sulphuric acid

We know that dilute $\ce{ H2SO4}$ doesn't react with copper because copper has higher reduction potential ($0.33$) as compared to hydrogen ($0.00$). However, it reacts with conc. $\ce{H2SO4}$ and ...
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Hydration in Chloral [duplicate]

Chloral consists of two OH bonds on the same carbon, which is usually unstable, and leads to the evolution of a water molecule, and converts into an aldehyde. However, this is not observed in chloral, ...
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Hydrogen peroxide on damp clothes left out in the sun [duplicate]

Somebody told me that sunlight is a good bleach for clothes because leaving damp clothes outside in the sunlight will turn some of the water into hydrogen peroxide. Is this true. If yes, then why can'...

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