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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nucleophilic attack in Acid chloride formation

First mechanism is the one taught in lecture, and I wondered why the electrons from carbonyl Oxygen wouldn't react with thionyl chloride. So I tried to draw a second mechanism as much as I could but ...
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77 views

Mechanism in Acid chloride formation

I want to ask about nucleophilic attack by Cl in Step 2. To me there seem 4 electrophilic sites and I marked them as (a)~(d). mechanism I've seen in lecture only deals with site (a). maybe (c) is ...
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825 views

mechanism in Birch reduction

at first I wondered why 2 H are added to opposite side of benzene like reaction below. because I could imagine 2 H added right next to each other or 1 C away from each other. so, looking for ...
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81 views

Will t-butoxide still form less substituted alkene when there is a possiblity for more stabilisation?

Consider this reaction: Will a usual Hoffman elimination take place or will a carbocation form by leaving of $\ce{Br}$ and rearrange to give a conjugated alkene like this one: I have heard that ...
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86 views

Effect of Steric Environment on Selectivity of Protection by Sisyl Chlorides

(sorry about the poor diagram. I don't know how to add in the arrows and stuff) Draw the product when the following compound is reacted with sisyl chloride in the presense of DMF catalyst at $\pu{-...
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171 views

Nitrogen oxides produced in diazotization

My A level exam board describes an experiment to produce methyl 2-hydroxybenzoate (methyl anthranilate) from methyl 2-aminobenzoate (methyl salicylate). I did the experiment as described (including ...
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44 views

Hypothetical concerted process feasibility

How feasible is the following hypothetical reaction, where both C and D are awful leaving groups (so the reaction must happen in one step)? I don't see a way how the orbitals could interact, so I ...
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500 views

Migration of R group in Hofmann rearrangement

In the mechanism of Hofmann rearrangement, one step involves migration of $R-$ group from carbon to nitrogen as shown: This reaction proceeds even if the migratory aptitude of the $R$ group is poor (...
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746 views

What are all products of an ozonolysis of alkenes using zinc and water?

I'm studying ozonolysis reactions in alkenes, and saw that in one of them there is the formation of $\ce{H2O2}$ (Can anyone explain from where?) that I presumed that reacts with $\ce{Zn}$, one of the ...
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43 views

Determining Reaction Orders

Can you figure out the reactant's reaction order (First-order, second-order, third-order, etc.) JUST by looking at a chemical reaction? What if you were given a multi-step reaction? A single step ...
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467 views

Regiochemistry and stereochemistry in synthesis of alcohols from cycloalkenes through oxymercuration and hydroboration

I have been posting several practice final questions for my organic exam next Tuesday. I have worked through all the questions, but my prof does not post the answers. I would greatly appreciate your ...
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140 views

Can a hydride shift be concerted?

I see that in most textbooks Alkanide shifts are shown as concerted mechanisms, but Hydride shifts are not. Why is this done? Shouldn't the rearrangement be concerted when the carbocation formed is ...
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91 views

I'm not sure I understand the stoichiometry of this mechanism

I was going through the experimental mechanism of nickelocene synthesis, and I looked through the notes and it said that there would be $\frac12$ $\ce{NiCl2}$. I'm sort of confused by the $\frac12$. ...
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300 views

Find the major product when Benzoquinone reacts with HBr

What is the major product when Benzoquinone reacts with $\ce{HBr}$ ? My effort: I thought it would be an $\text{SN}_{1}$ mechanism, but the carbocation at either double bond wouldn't be stable.
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777 views

Tele-substitution mechanism

According to IUPAC goldbook: A tele-substituion is a substitution reaction in which the entering group takes up a position more than one atom away from the atom to which the leaving group was ...
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68 views

Converting hydrogen to methane

I am in need of small amount of pure methane for laboratory purpose. I have hydrogen generator in the lab. Is there a possibility of generating methane from hydrogen ? May be make hydrogen flow ...
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163 views

a chemical model for pde

Consider the initial boundary value problem $$u_t=a(t)u_{xx},\,\,\,0<x<1,\,\,\,t>0$$ $$-ku_x(0,t)=hu(0,t),\,\,\,t>0$$ $$u(1,t)=u_0,\,\,\,t>0$$ $$u(x,0)=f(x),\,\,\,t>0$$ where $a(t)&...
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422 views

What radius best represents reaction distance?

Molecules must be within a certain distance for a reaction to begin as well as satisfying a myriad of other factors. Whilst the exact distance varies from reaction to reaction, is their any distance/...
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451 views

How do tie-line slopes affect raffinate/extract envelope in ternary phase diagrams?

I am struggling to understand ternary phase diagrams for reactor engineering. The course slides offer little to no help so I'm hoping to find an answer to this question How does the slope of the ...
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92 views

In which beta-elimination reaction do the structures of the carbocations formed influence the reactivity?

I believe there is a mistake. If we go back to the mechanisms, E2 does not go through a carbocation. So, there should not be any impact. E1 does however. So, E1 should be circled. Is there a missing ...
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476 views

What is the mechanism of a 1,2-hydride shift?

What is the mechanism of a 1,2-hydride shift? I read that there is an aromatic intermediate, in that the intermediate obeys Hückel's rule. However, Wikipedia doesn't offer any further explanation. ...
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968 views

Imine stability in acids and bases

I understand that imines can be hydrolyzed in acidic medium. But what about in basic medium? Can imines still be hydrolyzed? I have a plausible mechanism ... nitrogen's withdrawal of electron ...
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442 views

Most economical method to convert potassium oxide to potassium nitride.

I have a compound potassium oxide($\ce{K2O}$) and I am trying to convert it into potassium nitride ($\ce{K3N}$). Here are a few possible reaction methods : Split potassium oxide into the constituent ...
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784 views

Selectivity Coefficients of Ion Exchange Resins - Selectivity Reversal with TDS / Ionic Strength

I'm currently studying ion exchange resins and generally getting a bit stuck on some points of information which I do not fully understand / are not very well explained within the literature. I ...
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2k views

Mechanism of the Gatterman Reaction

Aryl diazonium salt on treatment with copper and the corresponding hydrohalic acid, gives the aryl halide. This reaction is called the Gatterman reaction. What is the mechanism of this reaction? Is ...
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1answer
510 views

Nucleophilic addition of grignard reagent

Here why isn't the phenyl group attacking the carbonyl carbon? Isn't the first step in addition of grignard reagent the attack by the carbanion on the carbonyl carbon ?
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1answer
817 views

Can the electrophile attack at the position of the NH2 group in nitration of aniline?

In the nitration of aniline, we observe the formation of a meta-substituted product (47%) almost as much as a para (52%). However, can't the electrophile attack at the position where $\ce{-NH2}$ is ...
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359 views

Which is more stable Ethyl carbocation or Neopentyl carbocation?

As per my knowledge, hyperconjugation is more dominating over inductive effect, so due to three alpha hydrogen ethyl carbocation should be more stable. In some books, while solving questions I ...
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90 views

Final product of the reaction of alcohol with CH3I in presence of strong base

Identify the final product (B) in the following reaction: I'm not sure how $\ce{NaNH2}$ and $\ce{CH3I}$ will react with the different types of alcohol present here. According to my solution,ether was ...
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26 views

Extent of multiple hydride shifts in a carbocation

Take this example: Multiple hydride shifts are possible only if in each step, the formed intermediate is more stable than the previous one. (1) to (2) converts $2^\circ$ carbocation to $3^\circ$ ...
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24 views

Function of sodium amalgam and CO2 in formation of aldohexose

There is this following conversion in my book: $$\gamma-\text{Lactone}\ce{->[Na/Hg +CO2]}\text{Aldohexose}$$ I'm not sure how this reaction takes place. I searched for mechanisms and couldn't ...
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36 views

Synthesis question: Using reductive amination to form pyrrolidine

What molecule results from treating 4-oxopentanal with $\ce{NH4Cl}$ and $\ce{NaCNBH3}$? Why? Is this a good, high yield reaction? I believe that pyrrolidine is formed because amination will convert ...
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39 views

Is methylchloride reaction with water SN1 or SN2

I wanted to know if methylchloride reacting with $\ce{H2O}$ would be SN1 or SN2. Methyl halide would not react using SN1 because methyl carbocation is very unstable but it would also not react using ...
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44 views

Mechanism of alkaline hydrolysis of cyclic amide

In this mechanism, I got a pretty different mechanism from the solution. From the model answer, there is an intramolecular proton transfer just before the formation of the carboxylate ion. However, in ...
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40 views

Maximum distance for intramolecular proton transfer

In this reaction (formation of ester from ketone / aldehyde), intramolecular proton transfer happens, since it can stabilize the formal positive charge by resonance after that. This transfer happens ...
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25 views

Acid catalyst choice on reaction of carbonyl group and O/N nucleophiles

For oxygen nucleophiles, e.g. $\ce{ROH}$, when reacting with a carbonyl group to form acetal, the acid catalyst used is protonated alcohol. for nitrogen nucleophiles, e.g. $\ce{RNH2/RR'NH}$, when ...
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32 views

Enamine Formation in a Diketone

I am trying to form an enamine, and I was trying to figure out if the following reaction is possible: Would this reaction terminate after the formation of the shown product, or will the other ...
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57 views

Can someone clarify this rationale for using polar, protic solvents in an Sn1?

In the textbook I am reading, it states that an Sn1 mechanism prefers a (polar) protic solvent because the protic solvent helps stabilize the carbocation and solvate the kleavin group, facilitating ...
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1answer
46 views

Aluminium, Carbon, Aluminium Sulphate battery. What's the reaction?

I made galvanic cells from the following items (while trying to do something else), and they give between 0.6 V and 1 V per cell. Aluminium foil – negative terminal Carbon (these work: charcoal ...
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38 views

Addition of HBr on alkene

In 1-chloroprop-1-ene(E), if we add HBr, where will the proton add to, C1 or C2? I am asking this because I can't decide whether mesomeric as well as negative inductive effect of Cl will dominate or ...
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24 views

Are SN1 reactions pseudo unimolecular first order reactions?

I believe the the Solvent (present in excess) helps in ionisation of R-X to carbocation in Rate Determining step so shouldn't the Rate Determining step be a pseudo-unimolecular reaction as 2 molecules ...
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Order of adding reactants on growth of Cu

I am reading the following paper which details the steps to control growth of Copper. They fabricate Copper powders from $\ce{CuNO3, NaOH, and C6H8O6}$. Specifically, in this paper they add the sodium ...
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28 views

Can the ion that isn't preferentially discharged discharge at the same time during electrolysis?

I would like to ask if the ion that isn't preferentially discharged can discharge at the same time during electrolysis. Also, is the ion discharged at a much smaller extent or just discharged right ...
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38 views

Understanding chemical reactions

I just got in 10th grade and the first chapter in Chemistry in our school curriculum is Chemical Reactions and Equations The chapter is littered with a lot of chemical reactions and their equations ...
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29 views

Can bond rotation take place in Pinacol-Pinacolon rearrangement

I was given a question of pinacol pinacolon rearrangement of butan-2,3-diol where the methyl groups were anti to the respective hydroxy groups. Can the C2-C3 bond be rotated to allow hydrogen to be ...
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31 views

How to add components in visual MINTEQ

I need to figure out speciation of a mixture of metal nitrates and chloroplatinic acid. I am using visual MINTEQ to do this. But platinum ion is not there in the visual MINTEQ component list. I need ...
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19 views

Mechanism of electron delocalisation from the other end of alicyclic chain

When one adds $\ce{Br2}$ and $\ce{CH2Cl2}$ to 5-Methylhex-5-enol, this mechanism follows; Also,in adding $\ce{Br2}$ to 2,2-Dimethylhexa-3,4-dienol, this follows; What is the mechanism here, in which ...
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34 views

Converting Chlorine Dioxide to Free Residual Chlorine

Our water treatment facility used Chlorine Dioxide to disinfect the produced drinking water. The analysis results indicate concentrations of 0.2 mg/l of chlorine dioxide at the source. Can we analys ...
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53 views

Could the Superoxide Radical Anion Be Responsible for the Removal of Chlorine Dioxide Used to Treat Natural Waters?

Some background facts: $\ce{ClO_2}$ is a gas that is highly soluble in water (some 8 g/L at 20 °C). However, per Wikipedia , to quote: It does not hydrolyze when it enters water, and is usually ...
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extract cellulose from CMC using cuoxam reagent (schweizer's reagent)

Good day, I am new in the field of chemestry. My question is, if it is possible to reverse or extract (I am not very sure how to say it), cellulose from carboxymethyl cellulose (CMC) by the use of ...

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