The detailed and 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, which seek information on elementary steps of these processes. It may be applied to hypothetical and/or proposed ...

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Mechanism of reaction between substituted aniline and potassium thiocyanate in presence of bromine and glacial acetic acid

Im currently doing this project where in we are synthesizing 2-amino-6-substituted benzothiazole by using p-substituted aniline with potassium thiocyanate in presence of bromine and glacial acetic ...
2
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1answer
31 views

Mechanism for oxidative cleavage of tertiary alcohols by NaOCl

I came across this today An ester $\ce{C4H8O2}$ on reaction with $\ce{CH3MgCl} $ and hydrolysis gives an alcohol. The alcohol on reaction with $\ce{NaOCl}$ and $\ce{H3O+}$ gives acetic acid. ...
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Nucleophilic Addition of Hydrohalic Acids

Hydrogen cyanide shows nucleophilic addition at carbonyl compounds' carbon to form a cyanohydrin. Alcohols, similarly, form acetals or ketals. Will hydrogen chloride - or hydrohalic acids in general - ...
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23 views

Does Ag react with NaOH? Or Ag2O with NaOH?

Can the reaction happen without water as a reactant (Ag comes to contact with NaOH by physical vapor deposition in a vacuum chamber)?
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0answers
24 views

What is the oxidation mechanism of gunpowder?

I've been recently looking into fireworks and the chemistry of explosives, and I found out that amongst others, one of the most important reactions in gunpowder ignition is the oxidation of charcoal ...
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1answer
39 views

Regioselectivity for electrophilic aromatic substitution with multiple strongly electron withdrawing groups

At which position will electrophilic substitution on p-cyanonitrobenzene occur? As both are -M groups, there are two possible sites of reaction, meta to each of the groups. The answer is meta to ...
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0answers
21 views

Steps in mechanism of pyruvate dehydrogenase

I am having some trouble with certain steps in the mechanism below (from Mike Lu on Proteopedia) detailing the mechanism of action of pyruvate dehydrogenase converting pyruvate to acetyl-CoA. In ...
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0answers
25 views

What prevents self-condensation in the Perkin reaction?

An acid anhydride is condensed with an aromatic aldehyde in the Perkin reaction. The latter is non-enolisable, and thus the former forms the enolate which attacks as a nucleophile. If the attack is ...
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1answer
41 views

What is an “attack” in Organic Reactions?

I began to study organic reactions and found the term "attack" everywhere, what this "attack" precisely mean?
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38 views

Iron chemistry: acetates for ebonizing wood

I have recently been “brewing” what is commonly called “iron acetate” for ebonizing wood, and I'd like to understand the chemistry of the iron/acetic acid reaction, which should be fairly simple, but ...
0
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1answer
36 views

Diethyl Ether reaction mechanism

I was trying to determine the reaction mechanism behind the production of diethyl ether. Looking at the ethyl alcohol + sulphuric acid method, I have come to the following conclusions for the reaction ...
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0answers
27 views

HCl used in hydrolysis of sucrose

I am aware that $\ce{HCl}$ can be used to help speed up the hydrolysis of sucrose but I haven't really been able to find out why. I've read somewhere that the glycosidic link in sucrose is broken off ...
8
votes
1answer
109 views

What's the reaction type of the Hydrogen shift?

Rearrangement of cycloheptatrienyl carbene yields heptafulvene via a hydrogen shift. I see that the reaction is favorable because there is a conjugative effect with the $\pi$ system of the ring in ...
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0answers
46 views

Check whether two compounds will react from their chemical structure

If I have the chemical structure of two organic compounds, [i just have the structure and molecular formula, not the name of the compound], is it possible to tell whether they will react or not? If so ...
7
votes
1answer
105 views

Mechanism of dehydration with phosphorous pentoxide

Dehydration of carboxylic acids with phosphorous pentoxide yields acid anhydrides, and in a similar reaction, amides dehydrated with phosphorous pentoxide yield cyanides. Can an arrow pushing ...
3
votes
1answer
29 views

Carbon/Silicon pentacovalent intermediate during substitution

During $S_N2$ reaction with a silicon compound, a pentacovalent intermediate is formed, while there is no such intermediate formed with carbon compounds (only a pentacovalent transition state). Why is ...
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1answer
32 views

Cleaning stains with hydrogen peroxide and bleach

A while back, I discovered that if you have a stain on a white shirt, you can remove it by putting hydrogen peroxide on the stain, then adding some bleach to it. I have used this for getting out ...
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0answers
39 views

Bromate forming in open water

According to this article, Los Angeles is facing a problem where bromate, a suspected carcinogen, has been forming in their open water supplies. They believe that the formation of bromate has to do ...
5
votes
1answer
66 views

How might ammonia be created in this mechanochemical reaction?

Can mechanical agitation catalyze reactions? It appears so (thanks to Mithoron for the pointer!). We observed the following: We were using 10-micron hBN powder to impact-plate copper bearings (e.g., ...
8
votes
1answer
143 views

Orbital correlation diagram for the cleavage of cyclopropylmethylene carbene

In the last exam we were asked to rationalize the mechanism of the cyclopropylmethylene carbene cleavage into acetylene and ethylene. In the lecture we discussed pericyclic reactions ...
2
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1answer
46 views

Why is the cathode reaction required in a fuel cell?

So, at the anode of a fuel cell hydrogen is split into a positively charged proton and an electron. Then, there is the membrane which can let only protons through to the cathode, whereas electrons ...
3
votes
1answer
50 views

Is hydroboration a pericyclic reaction?

According to Ahn.N.T "Frontier Orbitals" hydroboration isn't a pericyclic reaction because boron uses two AOs and not one. The same applies for cheletropic reactions, which aren't pericyclic either. ...
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0answers
32 views

Crossed Cannizaro reaction

Can the Cannizzaro reaction take place between two carbonyl compounds, one having no alpha-hydrogen atoms and the other having alpha-hydrogen atom(s)?
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0answers
39 views

Why does RCN attack the benzene ring in Hoesch Reaction?

In the Hoesch reaction, an alkyl cyanide reacts with a polyhydric benzene ring, and forms an imine salt by attacking the activated benzene ring. Most acid derivatives (and even alkyl cyanide itself ...
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0answers
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Mechanism of reaction with TsN3 [closed]

What is the mechanism of the attached reaction if the reagent is $\ce{TsN3}$ with $\ce{Et3N}$ in $\ce{CH2Cl2}$.
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0answers
100 views

Why does Mg react vigorously in NaCl solution and less so in water?

When you put $\ce{Mg}$ into water a few $\ce{H2}$ bubbles appear. But when you put $\ce{Mg}$ into a $\ce{NaCl}$ solution there is a vigorous release of $\ce{H2}$, why is this and what reactions are ...
4
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0answers
28 views

Why does a mixture of siloxene and cerium(IV) sulfate luminesce?

Not long ago, I performed an experiment where siloxene and cerium(IV) sulphate were mixed together. The mixture produced an orange-yellow glow. Why does it glow? What is it about the two chemicals in ...
5
votes
1answer
34 views

Understanding a chemical reaction from kegg

I came across a reaction that looks as follows: In this reaction the polyphosphate is common in both the sides of the reaction. Does this act as enzyme? But from the website it seems that the ...
3
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0answers
36 views

What is the degradation mechanism of pyrrole?

A vial of pyrrole monomer (that was occasionally exposed to air) changed its color while degrading from pale yellow to dark orange. What is the mechanism of pyrrole degradation? What are the ...
4
votes
1answer
64 views

Why don't periodic acids convert alkenes to 1,2 diols?

Periodic acids cleave 1,2 diols by forming an periodate ester as an intermediate. Osmium tetroxide also forms an osmate ester with alkenes and yields syn diols after a hydrolysis step. Given that ...
3
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0answers
38 views

How does the Kucherov reaction work if the alkyne is aromatic?

I know how the Kucherov reaction works for aliphatic alkynes, but what if the alkyne has a phenyl attached? How will the aromatic ring affect the reaction of alkynes with water?
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0answers
34 views

Grignard reaction - exchange of groups

Why is this reaction successful: Why doesn't metal-halide exchange occur easily to get Ar-MgCl and R-Br?
0
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1answer
39 views

Thermal decomposition of mercury thiocyanate

A video on YouTube shows the thermal decomposition of mercury thiocyanate. A strange thing I've observed is that $\ce{Hg(SCN)2}$, which is the reactant, is a white powder and the product is a ...
4
votes
1answer
86 views

Why can't LiAlH4 react with alcohols?

In the reaction of $\ce{LiAlH4}$ with carboxylic acids, deprotonation is followed by a step in which $\ce{O-AlH2-}$ acts as a leaving group. The mechanism is given here in this answer. $\ce{LiAlH4}$ ...
3
votes
1answer
77 views

Preparing an amine from an azide

Is there any mechanism available for reduction of alkyl azides to amines. One of the reactions is conversion by $\ce{Na}$ in ethanol or by $\ce{LiAlH4}$. But how do these proceed? $\ce{LiAlH4}$ will ...
2
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0answers
35 views

Selective nitro reduction of poly nitro compounds

Is there any way through which I could selectively reduce one $\ce{NO2}$ group from a dinitro- or trinitro- compound to an amine. I was reading Solomons and Frhyle and it says that m-dinitrobenzene ...
3
votes
0answers
23 views

Lemieux-Johnson oxidation on cycles

Consider the following molecule : What would it yield by a Lemieux-Johonson oxydation ($\ce{OsO_4,NaIO_4}$) ? My first guess would have been that $\ce{OsO_4}$ was likely to attack any of the bonds ...
3
votes
1answer
98 views

How can we balance one-half of an oxygen molecule, or any other diatomic, in a chemical reaction?

How can we balance oxygen or any other diatomic molecule with a fractional coefficient in a reaction? I mean, if we can balance oxygen atoms in an odd number what happens to other oxygen atom, and ...
0
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1answer
47 views

Is there any reaction between amines and AgNO3?

I found a question in a book about the reaction between $\ce{AgNO3}$ and aromatic/aliphatic amines, but I couldn't find any information about it.
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1answer
66 views

Functional Group compatibility in organic chemistry [closed]

As a continuation to the question: Predicting reaction among compounds I found the list of functional group on wikipaedia: ...
3
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1answer
74 views

Esters of catechol - Fries rearrangement

Esters of catechol undergo the Fries rearrangement But one product is formed more than the other. I believe it is due to the electron withdrawing nature of the $\ce{OCOCH3}$ group which prefers ...
8
votes
1answer
73 views

The appliance of LAB in amide reduction

Lithium aminoborohydride is a versatile reducing agent. In the scheme below, I don't understand how does unhindered LAB afford an alcohol in the reduction of amides while a hindered LAB affords an ...
3
votes
0answers
80 views

Oxidation of alkyl side chain using KMnO4

I was reading about side chain oxidation of alkyl side chains of benzene using alkaline $\ce{KMnO4}$ and heat. My book (Solomon's and Frhyle) says that this is only for compounds having a benzylic ...
-1
votes
1answer
40 views

When there is elimination and when there is nucleophilic substitution

I am studying organic chemistry for quite a time now, but this is the general problem I come across. Both seems likely. I only know that heat causes elimination, but this does not appear to be the ...
7
votes
2answers
67 views

Mechanism of initiation in contact explosives?

It's well known that undiluted nitroglycerin will explode when subjected to a physical shock. What is happening as a result of the physical shock that sets off the explosive reaction? In particular, ...
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0answers
25 views

Major product of the following reaction? [duplicate]

I think the product will be (d) due to pinacol pinacolone rearrangement but that reasoning is given wrong .Please help.Reaction mechanisms are necessary.
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1answer
92 views

Synthesis of phenoxyacetone from phenol

How can phenoxyacetone be synthesized from phenol? My Attempt: We would first need to deprotonate phenol by addition of NaH in THF and then add bromopropene. I'm not quite sure where I would go ...
4
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0answers
23 views

Stereoselectivity of 1,3 dipolar additions

How do the 1,3 dipolar additions follow the endo rule as in the reaction below where the anti diastereoisomer is formed predominantly?
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1answer
195 views

What is the major product of the reaction given?

I think the substituent of option (a) should attack the meta position as the resultant carbanion gets stabilized by an inductive effect, but no such compound is given. So where am I making a mistake? ...
3
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1answer
175 views

Reaction of alcohols with PCl5 and PCl3

The reaction of alcohols $\ce{ ROH }$ with $\ce{ PCl5 }$ and $\ce{ PCl3 }$ yields an alkyl halide $\ce{ RCl }.$ With $\ce{ PCl5 }$ the reaction is quite simple leading the formation of $\ce{ RCl }$ ...