Questions tagged [organic-oxidation]

For questions about oxidation reactions in organic chemistry, where a molecule of interest is oxidised. Do not use for questions on general redox concepts.

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Elbs persulfate oxidation

Can anyone suggest the mechanism of Elbs persulfate oxidation. The image of the question has been attached below. Although I had posted a similar question earlier but someone ruled it out as homework ...
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Mechanism of Elb's Persulfate Oxidation of Phenol [closed]

Please suggest the elaborate mechanism of Elb's Persulfate Oxidation of Phenols. Refer to the image attached below as per a question in manuals.
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Combustion and oxidation

What is the difference between combusting and oxidizing? Oxidation of alcohols leads to formation of aldehydes and carboxylic acid whereas the combustion of alcohols leads to the formation of carbon ...
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40 views

Does formaldehyde and ethylene glycol give positive Fehling's test?

Fehling's test follows a single electron transfer mechanism, with electron transfer form the substrate to $\ce{Cu^2+}$, which forms $\ce{Cu^1+}$finally giving reddish brown precipitate of $\ce{Cu2O}$. ...
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What product will be formed from the side chain oxidation of 4‐ethyl‐1,1‐dimethyl‐3,4‐dihydro‐2H‐naphthalene?

Benzylic hydrogen is required for the side chain oxidation of benzene. But for this compound the top branch connected to the benzene ring does not have a benzylic hydrogen. So, will the top branch be ...
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1answer
50 views

Why is the silver salt ammoniated to form the Tollen's reagent? [duplicate]

When doing a distinguishing test between aldehydes and ketones using Tollen's reagent, is it necessary to convert $\ce{Ag+}$ ions into $\ce{Ag(NH3)2+}$ in order to oxidize the aldehyde?
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Doubt in dehydrations of alcohol where ring expansion may be involved [duplicate]

I came across this question in my book. Now I have always thought that alcohol dehydration takes place through E2 mechanism when primary carbocation is involved. So I made the following product for ...
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61 views

Reaction of Tollen's reagent with 7‐oxabicyclo[2.2.1]heptan‐1‐ol

Identify whether the given compound will get oxidised by Tollen's reagent. The problem here is with the bridged alpha carbon. It cannot pertain sp2 character in the middle of the reaction as it is ...
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3answers
83 views

How does copper oxidise alcohols?

Consider for example ethanol being heated in the presence of copper at 300 °C. How does it give ethanal as a product? Copper being in its elemental state (oxidation state 0). Since negative oxidation ...
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2answers
53 views

Major product in reaction of butan-2-one + selenium dioxide

When reading about $\ce{SeO_2}$ I read this following reaction: $\ce{CH3CH2COCH3 ->[SeO2] CH3CH2COCHO + CH3COCOCH3}$ In the following reaction it was stated that $\ce{CH3CH2COCHO}$ was the major ...
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1answer
55 views

On the molybdenum(III) oxide-catalysed oxidation of alkanes to carbonyls

The following reaction is specified in my notes; $$\ce{CH4 ->[Mo2O3, \Delta]HCHO}$$ The intermediate steps involve the dehydration of an alcohol to yield the final product. Wouldn't this only work ...
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1answer
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Periodic acid oxidation of carbonyls?

The following reaction seem to be valid; $\ce{CH2OH-CHOH-CH2OH ->[HIO4]CH2O + HCOOH + CH2O + 2H2O}$ Apparently, there are similar reactions by 2,3-dihydroxypropanal, and also by the straight chain ...
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Nanocellulose suspension in water being dialysed in ethanol

I am working on nanocellulose. To prepare the sample for silanization, the first step is to dialyse the preparation in ethanol overnight. I wonder why this is a necessary step. Sorry, I am a physicist ...
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Mechanism for Ce(IV) Oxidation of Naphthalene

S. Cotton's Lanthanide and Actinide Chemistry reports that naphthalene can be oxidized to naphthalene-1,4-dione using cerric ammonium sulfate (CAS), $\ce{MeCN, H2SO4},$ and $\ce{H2O}$.1 No mechanism ...
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1answer
87 views

Why is the molozonide adduct thermally unstable?

In the mechanism of alkene-ozonolysis, the intermediate molozonide adduct, which is a cyclical but symmetric molecule (shouldn't symmetry about the C-C single bond bring stability?), decomposes ...
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1answer
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TEMPO Radical Analogue

After investigating what makes the persistent radical TEMPO stable, I was wondering if another compound which is more feasible for my needs would be comparable to it. Would oxidizing 2,2’-dimethyl-...
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109 views

What reaction is used for calculating pH of the solution obtained after ethanol oxidation with potassium permanganate?

If $\pu{30.0 ml}$ of $\pu{0.20 M}$ ethanol solution reacts with $\pu{1.80 g}$ potassium permanganate, what will be the final $\mathrm{pH}$ of the solution? Assume a complete reaction and that only the ...
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1answer
29 views

Degassing HI from Reaction (Via Ultrasound Maybe?)

I'm just going to put the questions first and the explanation after in case y'all don't have the patience. I want to know if it's reasonable to think that : Using an ultrasonic bath on something like ...
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What's the chemical reaction between NaOCl and Brilliant Blue dye?

Based on my research NaOCl dissociates into Na+ and OCl-. Looking at the photo, how does the OCl- ion and the brilliant blue dye structure end up as the product? How does the OH attach itself to the ...
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1answer
61 views

Does CH3COOH + H2O (vinegar) lose its antibacterial and antiviral properties when exposed to air?

I have been reading about using CH3COOH + H2O (vinegar) as a mild antibacterial and antiviral agent. For example: https://pubmed.ncbi.nlm.nih.gov/15698693/ Note, before anyone gets confused (or ...
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250 views

How does steam prevent oxidation in tea leaves?

I recently started branching out into different "flavors" of tea. In this endeavor I've been learning more and more about different varieties of tea and was wondering if anyone could offer ...
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What happens when unsaturated primary alcohol is reacted with acidic potassium dichromate? [closed]

It is clear that the hydroxy group in the substrate gets oxidised to carboxylic acid. But what happens to the double/triple bond in the unsaturated primary alcohol when it reacts with acidic potassium ...
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Which group will migrate in this BVG oxidation?

I know that H has a higher migratory aptitude order than phenyl. But, in this case, the phenyl ring has electron donating groups attached to it which enhances its migratory aptitude. So, which group ...
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1answer
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Why is potassium permanganate used to kill mollusks?

I know that potassium permanganate is used as a disinfectant for bacteria. Permanganate acts as a strong oxidizing agent that can rip the electrons off of bacterial cell membranes, resulting in a ...
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1answer
66 views

Counting electrons in Ozonolysis [closed]

I can't understand the electron count made on this page about Ozonolysis. (http://ursula.chem.yale.edu/~chem220/chem220js/STUDYAIDS/ozonolysis/Oz.html) This is the specific part of the article: From ...
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1answer
34 views

Relationship between microplastics and wildfire smoke [closed]

My understanding is that: microplastics are short fragments of previously long polymer chains; wildfire smoke largely consists of incompletely burned organic materials such as wood. Wood burns by ...
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77 views

Mechanism for oxidative workup of ozonide

Oxidative workup of ozonide produces ketone (in case both the substituents of carbon are alkyl groups) or carboxylic acid (in case one of the substituents is hydrogen), depending on the alkene. I have ...
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1answer
530 views

Oxidation of alcohols by Ceric Ammonium Nitrate

I have realized that reaction with ceric ammonium nitrate essentially results in coordination of alcohol with $\ce{Ce(IV)}$ and my teacher referred that we should be able to proceed it to form ketone ...
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38 views

How do I get the smell of Febreeze (uncomplexed cyclodextrin composition) out of my carpet?

Help! I sprayed my old carpet, which had gotten a little mildewy from some wet towels left on it, with Febreeze original scent. Now I can't get that horrible scent out! It might also be mixed with ...
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72 views

Reaction of a cyclic tertiary alcohol with chromic acid

We know that $\ce{H2CrO4}$ cannot oxidize tertiary alcohols. The mechanism is: Now the ${\alpha}$ carbon does not have any hydrogen to proceed to next step. Therefore, this reaction would not occur. ...
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665 views

Oxidation of hydroxyl groups of glucose

In all oxidation reactions of glucose, it seems that the aldehyde group alone gets oxidised and none of the hydroxyl groups. In one reaction with nitric acid, the aldehyde group and the terminal ...
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1answer
86 views

Baeyer-Villiger Oxidation restricted to Ketones

According to Wikipedia, Baeyer Villiger oxidation occurs at the electron deficient oxygen site, with elimination of the carboxylate ion, and migration of an R group. But it is restricted to ketones ...
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How much oxygen is used up by the browning of an apple?

This is inspired by a recent popular question on Cooking. Let's assume that I take some apples, cut them up, and place them in a hermetically sealed container. Then the container goes into the fridge. ...
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218 views

Oxidation of ethanedioic acid with potassium permanganate

What are the products of the reaction of 1,3-butadiene with hot $\ce{KMnO4}$ (excess)? I know that $\ce{KMnO4}$ will first cleave the double bonds and we should get $$\ce{CH2=CH-CH=CH2 ->[KMnO4] ...
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Identification of the organic compound

An organic compound A $(\ce{C10H14O})$ exhibits following characteristics. A) It reacts with metallic sodium to give a colorless odorless gas. B) It is oxidized by $\ce{KMnO4}$ to benzoic acid. C) It ...
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Oven safe dessiccant?

Im sure there is a chemist/lab tech that knows a simple solution to my problem, as I cant seem to find a solution. When trying to strip and re-season cast iron cookware, I occasionally have problems ...
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1answer
435 views

Why do alkylarenes react with alkaline KMnO4, but not benzene? [closed]

Benzene($\ce{C6H6}$) does not react with alkaline $\ce{KMnO4}$, however alkylarenes react when there are benzylic hydrogens. What could be the reason for this? Thanks in advance
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Why doesn't HIO4 cleave acetals?

Recently, I started reading about the cleavage reactions done by $\ce{HIO4}$.I came across a statement which read $\ce{HIO4}$ can't cleave acetals but it can cleave hemiacetals. But when I tried to ...
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2answers
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Why can't we oxidise allylic alcohol to aldehyde using pyridinium chlorochromate? [closed]

I read in my book that we cannot use pyridinium chlorochromate (PCC). Why is that?
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m-CPBA Selectivity between Baeyer Villiger Oxidation and Epoxidation?

If both a ketone and an alkene are present in a molecule and you add one equivalent of m-CPBA, what are the factors that determine which group will be oxidized, the ketone through Baeyer-Villiger ...
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2answers
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Oxidation to allylic alcohols without stoichiometric metal reagents

Common methods of oxidation of alkenes to allylic alcohols in one step usually use stoichiometric metal oxidants, e.g., sodium dichromate. Without using this type of reagent, are the other methods ...
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What is the order of adding chemicals in Hummers method for graphite oxide?

I am trying to make graphene oxide but failing miserably. The XRD peak is at 24 (2θ) instead of being near 10. Raman shows correct g and d peaks but are not very sharp. The colour of the end product ...
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What is the product of following iodoform reaction?

Question Attempt I think the product A would be as I have attempted below, but I am getting the answer as A but book says D. Where am I wrong? Please help.
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666 views

2-Methylpropan-2-ol and Iodoform test

Can 2-methylpropan-2-ol be converted into methyl ketone the action of $\ce{I2}$ in the presence of alkali base and thus give iodoform test? Answer given to this question is that it can't give ...
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Mechanism of alkene dihydroxylation with potassium permanganate

I have scavenged the internet for different mechanisms for permanganate-mediated alkene oxidation and have found satisfactory mechanisms for oxidative cleavage and dihydroxylation under basic ...
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1answer
369 views

Reaction of 1,2-diketones with periodic acid [closed]

$\ce{HIO4}$ can oxidise alcohols. But does $\ce{HIO4}$ undergo any reaction/act as oxidant with 1,2-diketones?
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1answer
1k views

Action of KMno4/H+ and heat in this reaction

The first step uses LAH which is a hydride donor. So H- attacks any one carbonyl carbon and forms an aldehyde and acid attached to the ring. Then Conc. KMno4 is used. As far as i know, it cleaves c=c ...
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1answer
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Organic chemistry [closed]

Could someone tell me what happens when a compound having a benzene ring reacts with a mixture of NaOH/HCHO? What reaction and mechanism does this follow?
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1answer
73 views

Do all anhydrous organic matter burn? [closed]

All organic matter seems to be inflammable when dried up. Petroleum, Alcohol, Wood, and Coal burns readily. Can I call it a general rule? Are there known exceptions? What makes them the exceptions?
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Residue from biomass incineration [closed]

What gasses are typically produced when biomass is incinerated at high temperatures (600 C) in high oxygen environments and what is a typical composition of the ashes left behind?