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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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
81 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 ...
3
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1answer
65 views

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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41 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 ...
3
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1answer
28 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 ...
3
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54 views

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 ...
2
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1answer
55 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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233 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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46 views

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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17 views

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 ...
2
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1answer
66 views

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
63 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
33 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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61 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
427 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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28 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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55 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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2answers
485 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
81 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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54 views

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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0answers
180 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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562 views

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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2answers
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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
338 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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316 views

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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2answers
994 views

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 ...
3
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2answers
55 views

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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0answers
34 views

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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0answers
75 views

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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1answer
570 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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358 views

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
296 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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2answers
87 views

Chirality and number of sterioisomers

I have recently read that the number of sterioisomers in a compound having n chiral centres is 2^n. (That is, if no meso form is present) The below question asks for the number of sterioisomers in ...
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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
67 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?
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56 views

Does an aryl compound with any functional group attached to it, undergo benzylic oxidation? [duplicate]

> If you look at this compound, only the benzylic carbon on the top has a hydrogen attached to it, so how do we oxidize only the top part without touching the lower one (not sure if this product is ...
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0answers
17 views

Is there any way of testing antioxidant ability of different substances?

For my investigation, I am looking at the antioxidant levels of different types of tea. How could I compare the antioxidating ability of each tea? For example, I know there is a method calling for ...
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1answer
861 views

Does Glycerol give silver mirror test with Tollen's Reagent?

I did an experiment in my school lab in which we had to identify the given organic compound. In my Lab Manual, it's written: Take 2 ml of Tollen's Reagent and add a few drops of organic sample. ...
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2answers
334 views

Is aluminium foil pure aluminium? [closed]

Is aluminium foil pure aluminium? Or does it have other elements in the e.g: tin (Sn) or lead (Pb)? Because when I try to oxidize it through the process of submerging it in water, it doesn't look like ...
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1answer
62 views

Converting cyclic compounds to their corresponding aliphatic compounds

Is there any reaction available to convert cyclic compounds to their corresponding aliphatic compounds? eg. Converting cyclohexane to n hexane
2
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1answer
162 views

Why glucose and other similar carbohydrates are oxidised fully by HIO4?

$\ce{HIO4_{(aq)}}$ requires the vicinal diols to have syn configuration, as it forms a cyclic periodate ester. But glucose does not have syn configuration at C3, and if you consider cyclic forms of ...
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0answers
39 views

Oxidation of ascorbic acid (Vitamin C) [closed]

What would you suggest me to use for oxidation of vitamin C to dehydroascorbic acid instead of bromine water?
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1answer
309 views

Mechanism of the reaction of cyclohexanol and concentrated nitric acid to form adipic acid [closed]

If someone could please give me the hint to how the initial attack is carried out, it'd be a huge help.
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1answer
486 views

What is the oxidation state of copper in Gilman's Reagent? [closed]

What is the oxidation state of copper in Gilman's reagent? In $\ce{R-Cu}$ bond the oxidation state is +1. Thus in $\ce{R-Cu-R}$ bond the oxidation state has to be +2. But if that so why positive $\ce{...
2
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0answers
59 views

Do tertiary ethers tolerate oxidative workup of an ozonolysis reaction?

I am attempting to cleave a double bond into a carboxylic acid and carbon dioxide using an ozonolysis reaction followed by an oxidative workup. I am concerned with the presence of a tertiary ether in ...
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0answers
93 views

Rate determining step in oxidation of alcohols using chromium-related compounds

I wanted to ask a question about the kinetics of an oxidation reaction using chromium reagents. I was given a lecture today on the mechanism of alcohol oxidations using Chromate (VI) reagents: My ...
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0answers
951 views

Oxidation of certain acids by potassium permanganate

Why does potassium permanganate oxidize formic acid and oxalic acid, but has no reaction with benzoic acid and acetic acid? The reactions were heated in a water bath (~70-80 °C). Oxalic acid had ...