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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30 views

Why don't periodic acids cleave 1,2 diols to ketones?

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 ...
2
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0answers
28 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?
2
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0answers
22 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
36 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 ...
3
votes
1answer
74 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
70 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
votes
0answers
27 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
20 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 ...
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0answers
15 views

how could we balance Oxygen or any diatomic molecules as fraction i mean if we can balance oxygen in odd number what happen to other mono oxygen [duplicate]

how could we balance Oxygen or any diatomic molecules as fraction i mean if we can balance oxygen in odd number what happen to other mono oxygen and Brian you mean in molecular level it is impossible ...
3
votes
1answer
89 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
votes
1answer
40 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
54 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
57 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 ...
4
votes
0answers
34 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
55 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 ...
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1answer
37 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
59 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, ...
0
votes
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.
1
vote
1answer
85 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?
1
vote
1answer
181 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
votes
1answer
94 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 $\ce{ RCl }$ ...
7
votes
3answers
673 views

Why is more of a catalyst added, when it is not consumed?

… catalysis, the acceleration of chemical reactions by substances not consumed in the reactions themselves—substances known as catalysts. (Source) Now as I’ve understood, to keep a reaction ...
2
votes
1answer
52 views

Acid-catalysed Reaction of Ketone with Benzene to Make Benzyl Alcohol

Benzene shows electrophilic substitution reactions. Normally, anything that can generate a carbocation shows, for example, a Friedel-Crafts alkylation reaction. I wanted to know if this reaction is ...
6
votes
0answers
49 views

Is it possible for a group to substitute itself?

When I first learned about substitution reactions, I started wondering something that I never ended up figuring out: Suppose you have a strong nucleophile which is also a good leaving group, such as ...
6
votes
1answer
107 views

Search for the last step of an altered Raschig process reaction mechanism

The Raschig process (according to the german wikipedia) is divided in the following steps: $\ce{2NaOH + Cl2 -> NaOCl + NaCl + H2O}$ $\ce{NaOCl + H2O -> HOCl + NaOH}$ $\ce{HClO + NH3 -> ...
6
votes
0answers
38 views

Nucleophilic Aromatic Substitution by Grignard's Reagent

Nucleophilic substitution through an elimination-addition mechanism (involving benzyne formation) occurs with a strong base. $\ce{NH2-}$ can show this reaction. Can $\ce{MgRX}$, which forms $\ce{R-}$ ...
3
votes
0answers
32 views

Ziegler-Natta polymerization regioselectivity

Why does the Ziegler-Natta polymerization display the regioselectivity shown in the image? Internal (coordinated to the metal) nucleophiles should attack the alkene on the less substituted end like in ...
12
votes
0answers
144 views

Why does hyperconjugation help for ring cleavage?

The question was to rationalize it the ring cleavage happens concerted or non-concerted. The papers "The Mechanism of the Thermal Decomposition of 1-Pyrazolines and Its Relationship to ...
3
votes
2answers
115 views

How does SO2Cl2 react with alcohols?

Is the mechanism similar to the reaction of $\ce{SOCl2}$ with alcohols? If not, then how is it different? We have been taught about the latter at school but my friend quizzed me about $\ce{SO2Cl2}$. ...
3
votes
1answer
42 views

Does esterification require reactants to be present in the same plane?

In the image that follows (7) I believe that the first step is the Cannizzaro reaction which will give (c) as a product. But since we are also adding $\ce{H+}$ in the second step, shouldn't an ...
5
votes
1answer
33 views

Stereochemistry of epoxide hydrolysis under acidic conditions

The epoxide on the top of the picture, in aqueous acid hydrolyzes to the compound below. What is the mechanism of this reaction? Standard epoxide opening in acidic conditions would happen at the more ...
3
votes
1answer
55 views

Stability of a carbocation, in part of camphor synthesis

Can someone explain to me why there is a rearrangement reaction of carbocation 1 to carbocation 2? To me the second carbocation appears to be less stable than the first because it is less substituted. ...
4
votes
1answer
45 views

POCP: How many ozone molecules can be created by one ethene molecule?

One ethane molecule can create two molecules of ozone, one ethanol molecule can create one molecule of ozone: In the following table the POCP is twice as high for ethene than for propane: From ...
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vote
1answer
57 views

Cannizzaro reaction and Aldol condenstion

Can all species that undergo aldol reactions also undergo Cannizzaro reactions? After all, the nucleophile can always attack the carbonyl group.
9
votes
2answers
240 views

Which compound reacts faster in the Cannizzaro Reaction?

Which reacts faster in the Cannizzaro Reaction? a) $\ce{OHC-Ph-NO2}$ b) $\ce{OHC-Ph-OCH3}$ A better hydride releasing group will be a better reactant, obviously. Therefore my answer was b, as ...
6
votes
0answers
140 views

Selenium dioxide oxidation

Allylic and benzylic compounds undergo oxidation with selenium dioxide to furnish either an allylic alcohol or an allylic carbonyl. But use of acetic acid as solvent stops the reaction at allylic ...
7
votes
0answers
48 views

Mechanism for anhydride formation

What is the mechanism by which phosphorus pentoxide ($\ce{P4O10}$) and a carboxylic acid form an anhydride? I can't find it anywhere online. Does $\ce{COOH}$ attack twice (I'm assuming it's the ...
5
votes
0answers
34 views

Can I make Ferrofluid without evaporating Ammonium?

I want to make ferrofluid, which is ferromagnetic particles suspended in a carrier fluid. Three methods I have seen involve using magnetic ink (for MICR codes), cassette tapes, or ferric chloride as ...
7
votes
3answers
190 views

Claisen condensation

Aren't two last steps superfluous? I just do not see how the fourth and last forms differ.
4
votes
2answers
194 views

What is the order of the reaction with respect to NO?

According to a question on my book, The following reaction mechanism has been proposed for the reaction of $\ce{NO}$ with $\ce{Br2}$ to form $\ce{NOBr}$ $$\ce{NO(g) + Br2(g)<=>NOBr2(g)}$$ ...
13
votes
1answer
2k views

Why super glue does not stick inside their own bottle?

We usually use super glue to stick any two objects but I was wondering like why don't they stick inside their own bottle ?
2
votes
0answers
46 views

Acid catalyzed Hydration

ATTEMPT: There are two possibilities for this reaction.The $\ce{H+}$ either adds to the $\ce{OH}$ group or the exo double bond. In the first case as $\ce{H2O}$ leaves giving us a stable allylic ...
4
votes
1answer
45 views

Anti elimination from vinylic halides

An $\mathrm{E2}$ (or $\mathrm{E1cb}$) mechanism requires antiperiplanar configuration. In case of restricted rotations, like in cycles, where rotation is not possible to achieve the antiperiplanar ...
6
votes
1answer
100 views

Why is the less substituted alkene favoured in Hofmann elimination?

In the reaction, $\ce{OH-}$ group attacks a hydrogen ion in an E2 reaction, forming a transition state in which simultaneously $\ce{NCH3}$ is removed. In this reaction, the $\ce{OH-}$ should attack, ...
4
votes
1answer
42 views

How does the MG811 sensor work?

The MG811 is an electrochemical sensor that measures $\ce{CO2}$. I think is something like a redox reaction but i don't understant how it produces $\ce{e-}$ so i can read them and get the $\ce{CO2}$ ...
9
votes
2answers
77 views

Nucleophilic character in polar protic and polar aprotic solvents

ATTEMPT: In DMSO (Di-methyl sulphoxide), there is no acidic hydrogen. So negative charge on oxygen will be concentrated as the anion will not be solvated by the polar aprotic solvent. Hence it ...
3
votes
1answer
34 views

In a nucleophilic substitution reaction, does the other atom to which the nucleophile is bonded matter?

For example, 1-bromopropane + $\ce{NaSH ->}$ Propanethiol + $\ce{NaBr}$ vs. 1-bromopropane + $\ce{H2S ->}$ Propanethiol + $\ce{HBr}$ Which is more valid, and why? Or are they equally valid?
3
votes
2answers
87 views

Does pressure affect non-gaseous reactions?

Pressure holds a great significance when it comes to reactions involving gaseous species. Changing pressure can affect the kinetics and even mechanisms of such reactions. However, does pressure hold ...
4
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0answers
39 views

What is the role of NaHSO3 in syn diol formation from alkenes with OsO4?

All I have found on this is that NaHSO3 reduces partially the osmate ester, so breaks off Os and leaves a syn diol. Is it possible to show this step with arrows showing the process of electron ...