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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Write the products of the reactions

What is the products of these reactions?
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Pyridine synthesis by tin(II) chloride reduction of 5-nitronorbornene

What is the reaction mechanism here? I guess the $\ce{SnCl2}$ reduces $\ce{NO2}$ to $\ce{NH2}$ but then what happens?
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Acid dehydration to ether

Can anyone please help me come up for a curved arrow mechanism for the reaction pictured? I'm familiar with the mechanism for the general acid catalyzed dehydration of butanol, where the arrow comes ...
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What is the mechanism for this intramolecular SN1 reaction?

What is the mechanism for the following intramolecular $\mathrm{S_N1}$ reaction? For this question, my professor hinted at an intramolecular reaction, and he asked us to recall the bromonium ion as ...
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Why do electron-rich aryl groups have greater migratory aptitudes?

In the following reaction there are three possible aryl groups that can migrate: an unsubstituted phenyl group, a p-methoxyphenyl group, and a p-nitrophenyl group: Why does the electron-rich p-...
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1answer
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Reaction of carboxylic acid with phosphorus trichloride

The reaction of carboxylic acid $\ce{RCOOH}$ with $\ce{PCl5}$/ $\ce{SOCl2}$ / $\ce{PCl3}$ yields an acyl chloride $\ce{RCOCl}$. With $\ce{PCl5}$ and $\ce{SOCl2}$ the reaction is quite simple utilizing ...
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Reaction of phosphorous pentachloride and sulphur dioxide [closed]

I came across this Reaction of $\ce{PCl5}$ and $\ce{SO2}$ which gives $\ce{POCl3}$ and $\ce{SOCl2}$. And I found this reaction to be interesting because of the fact that two gases are reacting with ...
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1answer
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Regioselectivity in coupling reactions of α-naphthol

I have seen in the following reaction of azo coupling where coupling takes place at position 4 of $\alpha$-naphthol. Now the electron density accumulation is similar at both position $4$ as well as $...
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Mechanism of addition of H-X to alkynes

Vinylic carbocation is unstable as the carbocation is bonded to a $\mathrm{sp^2}$ carbon that has high electron density, and pulls the electrons from the carbocation, which is already electron-...
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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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Mechanism for sodium metal test for hydrogen isocyanide

Sodium metal test is done for detection for acidic hydrogen. In this test, the given compound is treated with Na metal with and tested for the evolution of hydrogen gas. Compounds containing H ...
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Formation of toluene from (cyclobutane-1,2,3-triyl)trimethanol using conc. sulphuric acid

In my book this reaction is given without any mechanism: I thought that simple dehydration reaction is going to take place with rearrangement of the carbocation but I have no idea as to how toluene ...
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Alternate pathway of Gabriel synthesis to prepare secondary amine

Can modifying the Gabriel synthesis, which is generally restricted to synthesis of primary amines, be used to synthesise secondary amines? I have attached my idea regarding the synthesis (the final ...
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What drives the 'internal return' in SNi?

I just learnt that alcohols can undergo $\mathrm{S_N}i$ with $\ce{SOCl2}$ (without pyridine) to achieve retention: However, what I really do not understand is the 'internal return' step (forming '...
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Acidity of cyclopentadiene [duplicate]

Why is cyclopentadiene more acidic than dibenzocyclopentadiene although in the latter, the negative charge will be more distributed and consumed in resonance stabilization.?
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Mechansim of reaction between 1‐bromo‐2‐fluorobenzene and furan in the presence of Li/Hg

Problem From FITJEE AITS test series: What is the mechanism of the following reaction? Solution My approach It looks like Birch reduction with $\ce{Li}$ converting to $\ce{Li+}.$ But I can't make ...
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Most favorable position of attack of an electrophile on 4-trifluoromethyl-1,2-diphenylbenzene

Problem This problem is from a FIITJEE AITS paper Which position is most favorable for the attack of an electrophile? Answer My attempt The more favorable position for attack should be the on the ...
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Mechanism of R-OH to R-X using SOCl2 [duplicate]

https://youtu.be/ANlXQdpv6cc?t=1006 In this lecture, I am learning on the reaction of alcohol to alkyl halide using SOCl2 and pyridine. However, there are 2 different approaches on the first step. ...
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Reaction of acyl chlorides with diazomethane and silver(I) oxide

$$\ce{R-COOH ->[SOCl2,CH2N2][Ag2O/CH3OH] X}$$ While solving Carboxylic derivatives recently, I came across this. so following the reagents one by one- $\ce{SOCl2}$ will form acid chloride. $\ce{...
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Dependance of stability for reaction rate

In our book, it is given: Organic compounds are generally less stable than inorganic compounds. Due to covalent bonding in them, their reaction rates are often slow. First, it is said that they are ...
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How can I synthesize phenylpiracetam from styrene or benzaldehyde?

I am trying to design a proper synthesis route for phenylpiracetam. I am thinking a good starting material would be styrene or benzaldehyde. Here is my proposed route. Is there a better method? ...
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How to choose between an SN1 and SN2 reaction?

If a compound and a solvent is given, how do we decide whether the reaction proceeds via SN1 or SN2? I am asking this question specifically for a case where the substrate has the leaving group ...
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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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Rate of dehydration for butan-2-ol and butane-2,3-diol

A question taken from a test series (Vibrant, India): Amongst butan-2-ol and butane-2,3-diol, which has higher rate of dehydration? The carbocation formed in butane-2,3-diol is more stable as it ...
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Solvent shell collapse

In "advanced organic chemistry part A" book page:306&307 , the author uses the term 'solvent shell collapse' when talking about the reason for retention of conformation in tertiary ...
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Role of intermediate in determining the exothermic or endothermic nature of reaction

I was given a question to answer: Which of the following reactions is “not” exothermic? $\ce{CH3-Cl + CH3-CH3 -> CH4 + CH3-CH2-Cl}$ $\ce{CH3-Cl + (CH3)3-CH -> CH4 + (CH3)3C-Cl}$ $\ce{CH3-Cl + ...
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Reactivity comparison between benzaldehyde and acetaldehyde [duplicate]

One of my teacher says that $\ce{Ph-CHO}$ is more reactive than $\ce{CH3-CHO}$ in performing nucleophillic addition reaction because $\ce{—Ph}$ is planar and thus offers less steric hindrance as ...
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Reaction to form amino acid

$$\ce{CH2=CH-CH=O ->[CH3SH][(1,4 addition)] Product (P_1) ->[(i) NaCN][(ii) NH3\\(iii) H3O+] Q_1}$$ Correct statement regarding $\ce{Q_1}?$ $\ce{Q_1}$ is essential amino acid $\ce{Q_1}$ is ...
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How do I prepare 2-(3-azido-3-oxopropoxy)ethyl methacrylate from methacrylic acid?

I am having some trouble finding a proper synthesis route for the following product. Originally, I was thinking of reacting methacrylic acid with a large excess of ethylene glycol (along with an acid ...
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3answers
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Dehydration of primary alcohols without a β-hydrogen

What happens in dehydrations of primary alcohols (in presence of acid catalyst at high temperatures) which don't have a β-hydrogen? For example, in the case of neopentyl alcohol, will it dehydrate as ...
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Leaving Group Tendencies in Amide Hydrolysis

When we do hydrolysis of amides in basic conditions, we come across a mechanism in which the $\ce{OH-}$ ion attacks the carbonyl forming an intermediate as given in the photo: When the carbonyl gets ...
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What will be the major product when conjugated alkene (like 1,3-butadiene) is reacted with HBr in presence of R2O2?

What will be the major product when conjugated alkene (like 1,3-butadiene) is reacted with $\ce{HBr}$ in the presence of $\ce{R2O2}$? As we know, two products are formed when no $\ce{R2O2}$ is used ...
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Silver “polish” with aluminum foil left a hard yellow coat [closed]

I cleaned my silver teapot with the aluminum foil-baking soda-hot water method. Usually this works well on my silver plated flatware. However, this time it left a hard yellowish coating. I was only ...
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Cleavage of C-C bond in 1,2-diketo compounds with periodic acid

Today we learned the Malaprade reaction in class. My teacher told me that a similar reaction can take place when the substrate is a 1,2-diketo or 1-keto-2-hydroxy or even 1-hydroxy-2-amino(in presence ...
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Beckmann rearrangement v/s dehydration of Oximes

In the above question, A is an oxime, which is then reacted with phosphorus pentoxide. Now, phosphorus pentoxide is both a dehydrating reagent and a reagent used for Beckmenn rearrangement, but which ...
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Mechanism of conversion of Cr from FeCr2O4 (chromite)

The basic steps involved in the conversion of $\ce{FeCr2O4 -> Cr}$ involves, $$\ce{FeCr2O4 ->[NaOH / air, \Delta] Na_2CrO4 ->[C, \Delta] CrO3 ->[Al, \Delta] Cr}$$ Basically, I'm having ...
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Proton transfer in Claisen condensation mechanism

According to Wikipedia: In the second intermediate of the condensation, $\ce{OR-}$ act as a leaving group and reaction continue as expected. However, when forming the enolate in the first step, the ...
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Process of a substitution reaction

In this question I am not able to decide by what process this reaction is happening. I first thought that one of the $\ce{H}$ from $\ce{CH3}$ will depart $\ce{Br}$ from $\ce{CBrCl3}$ but I am wrong. ...
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Reactants used for manufacturing of mustard gas [closed]

A compound 'X' which is used in manufacture of mustard gas reacts with (ozone) $\ce{NH4Cl}$ to form 'Y' and elemental sulfur ($\ce{S}$). The compound 'Y' reacts with $\ce{NaOH}$ and $\ce{Ag}$ in ...
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What happens on heating an ester?

While solving a few questions a came across a problem which asked me what would happen when sec-butyl ethanoate was heated. I had never read about this reaction before and took to researching through ...
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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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What happens when an alkyne reacts with ammoniacal Cu2Cl2?

My text book provided me with 2 reactions concerning alkynes (Specifically Terminal Alkynes). The first one was the dimerisation of an alkyne on passing it through ammoniacal $\ce{Cu2Cl2}$. All was ...
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Fries Rearrangement Products

During Fries Rearrangement, oxygen donates its lone pair to $\ce{AlCl_3}$ forming $\ce{-O^+-AlCl3}$. Since this is a strong electron withdrawing group, shouldn't the final product be meta-substituted?
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Isomerization of phosphorylated 2-imino-1,3-dioxalanes into phosphorylated cyclic carbamates

I found a patent dating back to the Soviet Union. The patent number is 256764, and the patent describes the synthesis of phosphorylated cyclic carbamates. Here is a section of the patent, followed by ...
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Can pthalic acid or 1,2-Benzenedimethanol be possible products of Cannizzaro reaction of phthalaldehyde?

I know the main product that is ortho-hydroxymethyl benzoate ion but I think that phthalic acid and catechol must be formed also in very small amounts but I am unable to get any confirmation from the ...
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Kinetics of Sabatier reaction

I am modelling a methanation process in MATLAB, where I have a rate equation for methanation $$\ce{CO2 + 4 H2 → CH4 + 2 H2O}$$ in which I need partial pressure of $\ce{CO2},$ $\ce{H2},$ $\ce{CH4},$ $\...
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Ring expansion in cyclo compounds

In the following reaction, why does ring expansion not take place? Mechanism that was the correct one: In the second step when there is a protonated carbon the ring should expand to become 6 ...
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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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Difference in mechanisms between formation of acetal and enamine

When forming acetal from a C=O group with alcohol, the alcohol will act as a nucleophile and attack twice as the carbon is made very electrophilic twice. I wonder in the last intermediate before ...
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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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