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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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Mechanism of ring formation of an epoxide under acidic aqueous conditions

I am trying to figure out the mechanism of this reaction: $\huge{\ce {\ \ \ \ \ \ ->[H3O+] \ \ \ \ \ \ }}$ I think the $\ce{H+}$ will first attack the oxygen of the epoxide and another $\ce{OH-}...
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How do I decide whether ring will expand in this reaction or not?

Attempt: After forming the carbocation adjacent to the cyclopropyl ring I had two options, $\ce{Cl-}$ then and there without any changes Expand ring, form a new carbocation and add $\ce{Cl-}$ ...
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What is the mechanism of the reaction of a ketone with sodium nitrite/ hydrogen chloride?

What is the mechanism of reaction of a ketone with $\ce{NaNO2/HCl}$? Can $\ce{NaNO2/HCl}$ be considered as freshly prepared $\ce{HONO}$ here? I am confused about how the reaction will proceed.
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Reaction of ketones with sodium amide

Find the product of the reaction of dimethyl ketone i.e. $\ce{CH3C(O)CH3}$ with $\ce{NaNH2}.$ Should I do nucleophilic addition and form the product in the picture??
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Do fabrics assimilate airborne dioxins? [on hold]

Do natural or synthetic fabrics (clothing, etc) dissolve/trap dioxins and dioxin-like compounds from third-party/external sources such as airborne plastic fumes or soot? Also, is it safe to assume ...
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0answers
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Can dioxins be absorbed through the skin? [on hold]

I am aware that excessive/long-term exposure to dioxins dioxin-like compounds can cause skin problems (chloroacne) and their great affinity to lipids/fats, but I was wondering if the same occurs at ...
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1answer
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Which is easier, the nitration of toluene or the nitration of mesitylene (1,3,5-trimethylbenzene)?

Does the toluene can undergo nitration easier than mesitylene (1,3,5-trimethylbenzene), due to the high repulsion that will occur between $\ce{NO2}$ and the two adjacent methyl groups (in mesitylene ...
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1answer
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2-step reaction mechanism for the decomposition of NO2Br

I need to propose a 2-step reaction mechanism for the following reaction: $$\ce{2NO2Br -> 2NO2 +Br}$$ And prove the mechanism is consistent with: $$v=k[\ce{NO2Br}]^2$$ For the mechanism to be ...
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1answer
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Chlorination of propene at 773 K

The first step of preparation of glycerol with propene involves the chlorination of of propene at 773 K. It results to form allyl chloride. However the halogenation of alkenes generally give vicinal ...
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1answer
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Mechanism of oxidative dearomatisation with hypervalent iodine

The following step was taken from the synthesis of Kinamycin C on SynArchive. It employs the use of a peculiar reagent, that is, bis(acetoxy)iodobenzene (BAIB), also known as phenyliodine(III) ...
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Mechanism for Friedel-Crafts Acylation in Synthesis of Sertraline

In the first step of the synthesis of Sertraline, aluminium chloride catalyst was used in a Friedel-Craft's reaction to give the following product. My question is how does the exact mechanism work? 1-...
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1answer
821 views

Tert-butoxide in SN2 reactions

Can Tert-butoxide displace bromide via SN2 reaction? I read that Tert-butoxide is bulky and has steric hindrance, even with primary substrates. How is this reaction (picture below) possible? Source: ...
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1answer
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Do all reactants have appear in the first mechanism of the rate law?

I have the following reaction, $$\ce{CO + NO2 -> CO2 +NO}$$ The "second" mechanism is given: $$\ce{NO3 + CO -> NO2 + CO2}$$ So when searching for the first mechanism, I found this one to work: ...
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1answer
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Role of methanol in NaBH4 reduction

In reduction of carbonyls (aldehyde and ketones) to alcohols using NaBH4/Methanol, alkoxides are formed with the Boron which usually gets protonated on addition of water/acid. My question is what is ...
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1answer
483 views

What are the key chemical characteristics that determine the octane rating of fuel?

The octane rating of petrol (gasoline) is a measure of the how much compression a fuel air mixture can have before detonating (which in petrol engines is a bad thing as you want the mix to combust ...
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1answer
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Reaction of amines with diethyl oxalate (Hofmann Separation Method)

Why does only one molecule of secondary amine react with diethyl oxalate and two molecules of primary amine react with diethyl oxalate? I feel secondary amine also should have reacted similar to ...
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1answer
133 views

LDA and an aldehyde

Compounds A and B both react with LDA (lithium diisopropylamide, a strong base) to form the same anion C with the formula $\ce{C4H5O^-Li^+}$. I am unfamiliar with LDA. My first thought was that ...
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1answer
51 views

Why do metals form cations?

metals that have a low number of occupied shells such as lithium and potassium should have a stronger electrostatic attraction to their nuclei, so what causes them to always lose their electrons ...
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How is a ring formed when a carbon atom in an aliphatic chain attached to benzene ring has a positive charge?

This is my approach towards this problem. First off, a positive charge would appear in the C atom at the end of the chain, and then that carbocation would rearrange into a tertiary carbocation. But I ...
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0answers
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Reliable reaction predictor software [duplicate]

I am currently working on some novel techniques for synthesis,could anyone suggest a good reaction predictor software ,that may be reliable to a large extent ,so that I could anticipate my products to ...
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1answer
55 views

What happens in this reaction! Some hints needed

I understand step A involves reductive ozonolysis. and that step B is addition involves addition of ammonia to the carbonyl site to form imines. But what does the sodium salt of trichloroacetic acid ...
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Does this ring expand in this situation? What's the mechanism behind this? [closed]

So this is picture that sketches the situation. [EDIT] Thanks @glucose for putting me back on the rails. To wrap this all up and complete this topic, the answer to my question should be the product ...
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1answer
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What is the correct product of the Diels-Alder reaction between 2-ethoxybuta-1,3-diene and (Z)-acrylaldehyde-3-d?

What is the correct product of the Diels-Alder reaction between 2-ethoxybuta-1,3-diene and (Z)-acrylaldehyde-3-d? It keeps mentioning that my regio-selectivity is incorrect. And that I should ...
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1answer
50 views

Why primary alcohol follows SN1 mechanism?

Example 2: Identify all the products formed in the following reaction and indicate the major product. Solution: Three products will be formed in the given reaction as shown below: In ...
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1answer
42 views

Why doesn't open-chain glucose react with water readily in aqueous solution?

Though the exact number given varies from 0.02% to 3%, it's well agreed that glucose spends a very small percentage of its time in aqueous solution as a linear aldehyde. Glucose's overwhelming ...
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1answer
44 views

Can glucose and insulin exist in the same container without reacting?

Someone asked if glucose and insulin could be mixed in the same container and used as an injection to provide a quick energy boost. I'm not interested about the medical part of this question, but just ...
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0answers
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Organic Chemistry [closed]

This question was asked in the JEE exam held in India. I had a doubt between the 2nd and the 3rd options, whether a single chlorine atom or two chlorine atoms are added in the first step of the ...
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0answers
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What constitutes something being designated as big, bulky in terms of SN2 vs E2

When deciding between $\mathrm{S_N2}$ and $\mathrm{E2}$ for primary and secondary alkyl halides, is there a particular method or molecular size or any other threshold, which allows us to designate ...
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2answers
26 views

Negative charges in acid-catalyzed reactions [closed]

Whenever my professor draws a mechanism in an acid-catalyzed reaction, he always says you can't form negative charges. Why is that?
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2answers
34 views

What happens when mixing elemental mercury with sodium hypochlorite solution [closed]

Say you spilled elemental mercury from a thermometer and used household bleach on it, what would be the reaction if any?
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1answer
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Is isobutyl chloride or ethyl chloride more reactive in an SN1 reaction?

Compare the rate of $\mathrm{S_N1}$ reaction in the following compounds: We see that both compounds form primary carbocations. However, there is more hyperconjugation in the second compound as ...
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1answer
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What will form in the hydrolysis of urea in urine?

I just wanna know what is the end product of hydrolysis of urea in urine. I know that the hydrolysis of urea will form ammonia and a subsequent rise in pH but will the ammonia react with the water ...
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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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1answer
62 views

Hydrate decomposition equation steps

When a hydrate decomposes it loses water molecules in steps. Does each step have a chemical equation? If so is the following equations for decomposition of cupric sulfate hydrate correct? $$ \begin{...
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1answer
134 views

Organic chemistry. how to control the Friedel–Crafts alkylation rection to methylbenzene as the major product?

My question is due to a discrepancy I founnd in reactivity and organic conversions. In reactivity of organic compounds it has been established that an alkyl group activates the benzene ring and hence ...
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0answers
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method to certify the number of chiral carbons in fischer and haworth projection of glucose

While reading some notes about Glucose and its various projections: Fischer Projection: 4 chiral centres Haworth Projection: 5 chiral centres My doubt is that is there any (specific) method (...
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1answer
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Aldehyde and ketone reactions

Reagents to carry out above conversion, P, Q, R respectively are: (a) $\ce{H2C=CH-CH2-Br}$, $(\ce{HO-})$, $[\ce{HO-}, Δ]$, Wacker process. (b) $\ce{H2C=CH-CH2-Br(HO^-)}$, Wacker process, $\...
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1answer
91 views

The major product of the following reaction

Here,1,2-dibromobutane is reacted with i) alc. $\ce{KOH}$ ii) $\ce{NaNH2}$ in liq. $\ce{NH3}$ According to me, since alc. $\ce{KOH}$ causes dehydrohalogenation, using Saytzeff's rule the product ...
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1answer
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What is the minimum operating temperature of chemical hand warmers?

I have been looking at chemical hand warmers such as Hot Hands, Grabber and HotSnapZ. Unfortunately, I cannot find a minimum operating temperature for these types of devices. Logic tells us that they ...
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2answers
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Do alcohols react with alkyl halides?

I wonder if alkyl halides react with alcohols or not. I searched on Google but could only find reaction of alcohols with hydrogen halides
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1answer
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What is the mechanism of azulene synthesis?

In the Organic Syntheses preparation of azulene (http://www.orgsyn.org/demo.aspx?prep=CV7P0015) there are two reactions. First is a clevage of the C-N bond in pyridine and the second one is the ...
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Kinetics for E1cb reactions

We were taught that the kinetics of a reaction is determined by the reactions ‘rate determining step’ which is also the slowest step of the reaction. For E1 as well as E2 reactions the slowest steps ...
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1answer
184 views

When does a pinacol undergo dehydration or rearrangement?

What happens when the above pinacol is treated with - (a) conc. sulphuric acid (b) dil. sulphuric acid I'm confused between pinacol rearrangement and dehydration (E1 or E2?), as both possibilities ...
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1answer
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What do electrons usually do when lead acid battery is idle?

Lead acid batteries operation are governed by Redox reactions for charging and discharging. But, what do electrons usually do when lead acid battery is idle? And why? Assumptions: Say more ...
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Mechanism for ring contraction from 2-methylenecyclobutanol to 1-methylcyclopropanecarbaldehyde

I am stuck between two paths. I was going to protonate the alcohol to give a better leaving group, leaving a 2 degree carbocation and then go on with a hydride shift. But, I'm not sure what that may ...
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2answers
261 views

Finding all Chemical Reactions Given Products and Reactants

Suppose only a set of chemical formulas is given. How can you find all mathematically possible chemical equations whose educts and products are only from this set? Take e.g. the set $\{ \ce{C, H2, O2,...
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1answer
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Active methylene group nucleophilic substitution

The first product formed after reaction with $\ce{^-CH(COOEt)2}$ followed by hydrolysis is [2-(naphthalen-1-yl)ethyl]propanedioic acid: But is the reaction $\mathrm{S_N1}$ or $\mathrm{S_N2}$? On ...
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1answer
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Influence of protic and aprotic solvents on SN reactions [closed]

How does protic and aprotic solvents influence reaction mechanism considering SN1 vs SN2?
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How is energy released when a chemical bond is formed? [closed]

Chemical reactions are classed as endothermic or exothermic. Defn: exothermic (of a reaction or process) accompanied by the release of heat. The heat is released when the chemical bonds in the ...