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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46 views

Acidic cleavage of an ether

In the following question; Apparently, an SN2 reaction ensues, where the iodine atom's supposed to cleave off with the less sterically hindered alkyl branch from both the oxygens. This is the ...
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1answer
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Is the effect of hydroperoxyl radicals significant in the oxidation of organic compounds in the Fenton reaction? Why or why not?

In the Fenton reaction, a ferrous catalyst and hydrogen peroxide are used to generate hydroxyl radicals which in turn oxidise organic compounds. The reaction is commonly seen in the treatment of ...
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How does the reduction of phosphoric acid take place at the molecular level?

Phosphoric acid has been reported to undergo reduction when reacted with carbon at 850 °C. We can expect the products of the reaction to be H2, CO, and P2, but how would this reaction take place at ...
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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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Why is a benzylic cation more stable than a homobenzylic cation? [closed]

Below is a chemical reaction with $\ce{HBr}$. When this happening there are two out comes: One is $\ce{C6H5 - CH+ - CH(CH3) - CH3}$ and other one is $\ce{C6H5 - CH2 - C+(CH3) - CH3}$ when $\ce{C6H5 -...
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Does Br2/H2O oxidize all aldehydes including carbohydrates?

In many books, it is mentioned that aldehydes are easily oxidized even by mild oxidizing agents. However, I have never seen bromine water explicitly mentioned. But in the carbohydrates chapter, it is ...
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Stereochemistry and Mechanism of Addition Reactions in Alkenes [closed]

I have studied that some Addition reactions follow the Syn addition mechanism while some follow Anti. In case of halogenation, it can be understood that it is Anti addition due to the formation of ...
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Second order reaction with different reactants

In a laser photolysis reaction $\ce{C6H5NH2}$ $(C_0 = \pu{60 µM})$ is oxidized to its radical cation. The disappearance of the cation can follow three pathways: (1) Dimerzing of the cation, (2) ...
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Relative rate of solvolysis

I underestimated this question and just compared the carbocation stability of all the compounds (after removal of chloride via $S_N1$) and got the order D>C>B>A... but my answer is incorrect, what am ...
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859 views

Benzene to phenol in a single step

My teacher told me we can convert benzene to phenol within a single step using $\ce{V2O5}$/ $\ce{O2}$ at 300 ⁰C (not 500 ⁰C). Later I searched for that reaction but I couldn't find it in all over ...
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Change in rate of reaction with change in cofiguration [closed]

This was asked in one of our exams and I have no idea whatsoever Which of the following are correct: The answer is A,B and D. Why does change in configuration at a beta carbon cause so much ...
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Relationship between auto-ignition temperature with pressure and fuel

Experimentally it appears that increase in pressure, fuel concentration, and chain length causes AIT to decrease until a minimum where even further increase in these parameters increases the AIT. ...
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What is the “‡” symbol meaning in a reaction mechanism?

I was studying hydroboration from Clayden's Organic Chemistry [1, p. 1281] and the transition state had “‡” symbol in the upper right corner of the activated complex: We know that this is not the ...
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3answers
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SN2 reactions and inversion of configuration in compounds with more than one chiral centre

Suppose I have a compound with 2 chiral centres which are at (S,S). Now, suppose I have an iodine atom attached to the back carbon, and I wish to carry out an $\mathrm{S_N2}$ type substitution in a ...
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1answer
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Retrosynthesis of spirocyclic compounds?

I have been trying to complete this retrosynthesis problem for a few days but can’t figure out how to get from Ester starting compound to a spirocyclic compound. I have tried removing the Ester but ...
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What’s the results of combining LiF and carbon? [closed]

Which would you have to combine first in order for a safe or what would be the accurate way to combine LiF and carbon?
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Electrophilic attack of X+ on double bond

Is it the double bond attacking the $\ce{X+}$ ion or the other way around? Also, does it form a cyclic transition state if it isn't bromine or chlorine? Eg. cyclohexene $+ \,\ce{Cl+ ->}$ cyclic ...
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Which compound reacts faster in the Cannizzaro Reaction?

Which reacts faster in the Cannizzaro Reaction? a) $\ce{OHC-C6H4-NO2}$ b) $\ce{OHC-C6H4-OCH3}$ Obviously, a better hydride releasing group will react faster. Therefore my answer was b, as $\ce{-...
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Rationale behind Barton's rules for catalytic hydrogenation

Organic Chemistry by Morrison and Boyd,Seventh Edition says - When cyclohexanones are used as substrates, the stereoselectivity of the reduction is found to be dependent on the acidity or the ...
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Can PDMS silicone be produced with dichloromethane?

I was taking a simulated admission test for a Technology Institute (Brazilian ITA) and one of the questions asked for the production of PDMS silicone via these described steps: Reaction of $\ce{SiO2}$...
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1answer
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Is the following rate law possible for the given reaction?

A researcher is investigating the following overall reaction: $$\ce{2C + D -> E}$$ The researcher claims the rate law for the reaction is written as follows: $\text{Rate} = k[\ce{C}][\ce{...
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What are the organic reactions that are taking place in this reaction?

I know that A is the product of a Knoevenagel condensation between the aldehyde and the diethyl malonate, due to the acidic protons of the latter, but I don't know what the reaction between that ...
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1answer
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Use of Me2SOI/NaOH

In V triazole ($\ce{N^1}$) will substitute -Cl group. However from V to W, I don't get what $\ce{Me2SO+I-}$ in presence of base will do. Any hint? I also wish to know how to guess the reactions, in ...
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What is the mechanism for the reaction of alkenes with diborane and chloramine?

$$\ce{CH3-CH=CH2 ->[B2H6/THF][NH2Cl/H2O, Δ] Product (P)}$$ What is $\ce{Product (P)}?$ First of all, in this reaction I performed hydroboration to form an alkylborane. But I don't have any ...
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Elimination of tertiary alkyl halide with lithium aluminium hydride to give alkenes

I'm confused about the mechanism and thus cannot decide which alkene would be the product. Reaction with primary and secondary alkyl halides gives alkanes. What about this case?
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Reaction involving opening of epoxides

The following question was asked in an exam today: I chose the option (a), but the correct answer given was (b). Following is the explanation why I chose (b): Step 1 (Reaction with $\ce{PBr_3}$): $...
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3answers
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How does the equilibrium shift when concentration of reactant and product are increased simulatenously

Before answering my question, take a look at this example $$\ce{2NOCl <=> 2NO + Cl2}$$ Let's suppose I have 2 mol/l $\ce{NOCl}$, 2 mol/l $\ce{NO}$, and 1 mol/l $\ce{Cl2}$ in a closed system. ...
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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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How does methyl vinyl ketone dimerise with heating?

(A) to (B) is simply reduction, tosylation followed by intramolecular reaction and removal of tosylate. However, I am not able to guess how dimerization will take place, seems similar to Rauhut–...
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Does neighbouring group participation require an external nucleophile or can it happen on its own? [closed]

For example if I take a suitable substrate and dissolve it in a polar protic/aprotic solvent without any external nucleophile, will the internal nucleophile replace the leaving group? My line of ...
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Does halogenation by phosphorus tribromide lead to an inverted product?

I think it follows the SNi mechanism and would not lead to Walden inversion. Hence, the product should be (S)‐2‐bromobutane: But the answer says otherwise (the problem didn't indicate the presence of ...
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How does this brominated intermediate lose its methyl group?

The problem is such: So far my working has been: I'm concerned about the last step where the ester forms a ring. The methyl group doesn't look like a plausible leaving group, but it does not ...
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385 views

What is the mechanism for the reaction of an organic hydroperoxide with sulfuric acid?

The question asked to react the organic hydroperoxide substrate, $\ce{R-OOH}$, with dilute sulfuric acid, $\ce{H2SO4}$. In the last step, I removed a proton, making it act like a catalyst, along ...
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1answer
237 views

Distinguishing among SN2/SN1/E1/E2 for a secondary bromide

a. 2-Bromo-3-phenylbutane reacts with $\ce{NaOMe}$ in methanol. What is the mechanism? b. This compound then reacted with $\ce{CN-}$ in DMSO. What is the mechanism? My Attempt a. I am debating ...
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Elimination of bromide and acetate under reducing conditions

Here is the reaction that I didn't find the mechanism of: The conditions are zinc dust, acetic acid (solvent) at $\pu{11 °C}$ for 1 h. The reagents are sodium acetate; 2,3,4,5-tetraacetoxy-1,6-...
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Heating of Ethers with HI and Cleavage of Ethers

Question: Give the major product formed by the heating of the following ether with HI. CH3 | CH3-CH2-CH-CH2-O-CH2-CH3 My Attempt: According ...
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Electron flow: How does osmium tetroxide react with alkenes?

This is a question that has bothered me for some time.I have always thought that the part of one molecule will only attack part of another molecule if it has a higher positive charge.So with this in ...
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Possibility of SET mechanism of Wurtz reaction

I was studying the Wurtz reaction, and I wanted to figure out the mechanism. When I searched the web, I came across the single electron transfer (SET) mechanism explanation. How can the alkyl group ...
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Predicting the products for free radical rearrangement reaction [duplicate]

We were taught about rearrangement reaction and were given this homework: My attempt I cleaved the carbonyl bond homogeneously and proceeded to get product A; But I can't figure out the others; A ...
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Reaction most dominant product for a low concentration nucleophile

If i got this reaction, and I determine that it will react in a Sn1 mechanism, will the dominant product will be in the results of the EtOH/H2O or CN-? I think, the main product will be with the CN- ...
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Is there an adhesive that is not dissolved by acetone?

I am trying to glue glass sheets together to make a sealed 13" x 13" x 13" box. Inside this box there would be acetone gas used to melt 3D printed parts to make them more durable. Acetone will remove ...
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1answer
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How to convert benzene to N,N-dimethylbenzamide?

This is my solution to convert benzene to N,N-dimethylbenzamide. If you think is the right way, even just saying the equations are correct would help me! Thanks in advance.
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Mono-addition of HCl to unsymmetrical dienes?

I completed 3/4 of the answers, by choosing the correct reaction pathways leading to each of the 3 different products. But I don't know how to draw the reactant diene, I really thought what I ...
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Carbocation rearrangement in alkene addition reaction

This is a question from my textbook: Determine a step-wise $S_N1$ mechanism for the overall reaction: The solution shows the following carbocation rearrangement after Bromine leaves in the ...
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Migratory aptitude in E1 mechanism vs Pinacol-Pinacolone rearrangement [duplicate]

I wanted to know if the migratory aptitudes in chemistry are similar for all the reactions involving carbocation intermediates. For example, the dehydration of alcohols via E1 mechanism, what is the ...
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1answer
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Why does one bicyclic diastereomer react faster than the other one?

I have been asked to explain the following observation: I have a number of issues with this: 1) The fast reaction must be a syn-elimination. But how can syn E2 elimination occur? If an E2 ...
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2answers
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Why is hofmann product prefered here?

In the following reaction, Hofmann elimination is preferred. This reaction takes place by E1 mechanism. I thought the Zaitsev product would be major due to 1 extra hyperconjugating structure. In the ...
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Mechanism of acetylene formation from iodoform and silver

My book mentions a synthetic route for turning iodoform into propyne. That conversion was somewhat as follows: $$\ce{CHI3->[Ag] HC#CH ->[NaNH2] NaC#CH ->[CH3Br] CH3C#CH}$$ The first step ...
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1answer
65 views

How is carbon-halogen bond broken during Finkelstein reaction?

Finkelstein reaction is a halogen exchange reaction between haloalkane and a salt of a different halogenide: $$\ce{R−CH2−Cl + KI -> R−CH2−I + KCl}$$ From an answer of a previous question: As ...
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1answer
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Order of reactivity of substrates towards Wurtz reaction

In a book I refer, it is said that: Both Ionic [carbanion] mechanism as well as free radical mechanism are widely accepted for Wurtz reaction. When I read this statement, I was thinking, which of ...

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