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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Oxidation of Alkenes with Alkaline KMnO4

The mechanism of the oxidation of alkenes under acidic conditions with KMnO4 is pretty well known, but I can't seem to find one for alkaline conditions. All I found is that the MnO4- ion is reduced to ...
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88 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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2k views

In what way could benzoin give Tollen's test?

In Q29 of Joint Entrance Exam (JEE) 2016 India, the official answer key mentions that benzoin gives Tollen's test. However, I saw this post which says that it doesn't: Why do α-hydroxy ketones give ...
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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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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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1answer
33 views

Converting cycling 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
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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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2answers
3k views

How does pH affect the degradation of ascorbic acid (vitamin C)?

I know that vitamin C degrades over time (as I understand through oxidation). However, I am having trouble understanding how changing the pH of the solution in which the vitamin C is affects the rate ...
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2answers
79 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
52 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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Mechanism with hypohalite in haloform reaction

The haloform reaction is usually done in a solution of NaOH and $\ce{I2}$ (or indeed, any halogen). Now the first part of the reaction mechanism in the wikipedia page and in the most organic books ...
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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
64 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
86 views

Does the explosion of TNT include oxidation?

This comment below the question Rocket explosion compared to kT of TNT; has one ever knocked something over at a distance? suggests that ...TNT includes it's own oxidizer... Explosion isn't the ...
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1answer
103 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{...
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What exactly is an 'activated' alcohol? Benzylic vs. Allylic vs. Aliphatic

I'm currently writing a report about the oxidations of various alcohols using different catalytic systems. In all papers it is stated that benzylic and allylic alcohols are "activated", while ...
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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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1answer
110 views

Cheap but efficient disinfectant / biocide for home lab

EDIT I am forced to reword my question about a chemical mixing ratio. I have seen in Wikipedia that peroxide ($\ce{H2O2}$) and Acetic Acid can be mixed to Peracetic acid - this is an equilibrium. I ...
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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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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 ...
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1answer
121 views

Do secondary alcohols react faster than primary alcohols or is it the other around? [closed]

My questions is that do secondary alcohols react faster than primary alcohols or is it the other around? This for the oxidation of the alcohol to a ketone or an aldehyde. This reaction is with KMnO4 ...
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Reaction mechanism of thiol to disulfide oxidation under basic conditions?

I have been looking everywhere for an explanation to a reaction mechanism concerning the oxidation of DTT (or just thiols to disulfides in general) using oxygen as the oxidant. I'm aware that ...
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Can an alcohol oxidation to ketone happen with hydrogen peroxide? [duplicate]

As far as I know, usually $\ce{CrO3}$ and $\ce{KMnO4}$ are used for this scope, but can other oxidizers such as $\ce{H2O2}$ be used?
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Shi Epoxidation Issues - Any help would be appreciated

As part of my PhD project, I'm currently looking into running a Shi Epoxidation reaction. The first step is to reproduce the current literature on this reaction by using trans-stilbene as my substrate....
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Mixtures readily oxidzing organic matter [closed]

Are there other mixtures than piranha solution with similiar or better ability to completely and readily oxidize organic matter? Perhaps peracetic/performic acid?
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1answer
137 views

Usage of TFA in Pfitzner-Moffat oxidation and Collins vs Jones oxidation

Is the addition of TFA in Pfitzner-Moffat oxidation to protonate the DCC to form a positive carbocation for the alcohol to attack? Or is there more to it? Why is TFA used and not other acids? Are ...
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Chemical Reaction Alternative to O2 Respiration in H2/N2 Atmosphere [closed]

Note: If this question does not belong on this Stack Exchange, please direct me to a more appropriate Stack Exchange. This is a "creative chemistry" question as much or more-so than a "give me the ...
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42 views

Last steps of mechanism of Swern Oxidation

My question is regarding Swern oxidation. Why is the methyl group of the DMSO deprotonated and not directly the red hydrogen atom of the R2-CH-O bond deprotonated? Shouldn't it be that oxygen more ...
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Equivalents Triethylamine in Swern-oxidation

Hey folks, so I've been wondering why the use of 5 equivalents of Et3N in this case of a Swern-oxidation is necessary. I have done this reaction succesfully quite a few times now, but all the ...
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1answer
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Reaction between 1-methylcyclopentanol and potassium permanganate

In my basic organic chemistry class, I learned that only primary and secondary alcohols undergo oxidation (using $\ce{KMnO4}$). However, what is the outcome of reacting tertiary alcohol (1-...
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2answers
258 views

Is cyclic ether oxidised by periodic acid?

Is the three member ring of cyclic ether oxidised by periodic acid? As this also has oxygen attached to adjacent carbon so I think that cyclic ether of three members should be oxidised by periodic ...
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Oxidation of Aromatic Methyl to Aldehyde by CAN

I read in my text that Ceric Ammonium Nitrate is used for oxidation of primary alcohols. But the surprising part was that, according to the book, it could oxidise aromatic methyl group to a -CHO group....
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What reagents or series of reactions would allow for selective hydroxylation of an allylic methyl group outside of a ring?

Sample transformation for selective hydroxylation of an allylic methyl group outside of a ring. Selenium dioxide would not work since hydroxylation would be favored inside the ring.
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Epoxidation with peroxyacids

In this particular epoxidation/hydroxylation reaction, why does the epoxide only form at one of the double bonds and not both? The compound initially reacts with the peroxyacid to form an epoxide, ...
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Why is the titratable acidity of my wine going down as it ages and oxidises?

I am currently studying chemistry in grade 12 studies and I have come across a halt in my investigation. The experiment was to see how the increase in ethanol would lead to a more acidic wine, ...
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1answer
108 views

How do I remove tetrabutylammonium perchlorate from an organic synthesis?

I am trying to remove tetrabutylammonium perchlorate (TBAP) from an organic synthesis where TBAP was used as an electrolyte. I am working with compounds containing the amide group. I have used flash ...
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169 views

The products of a chain reaction beginning with acetone and sodium amide

I encountered the following question in an exam: $\ce{CH3COCH3 + NaNH2}$  giving out $\ce{A}$. $\ce{A}$ then reacts with $\ce{C2H2}$ giving out $\ce{B}$. $\ce{B}$ then reacts with $\ce{H+}$ to ...
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Oxidation of diols to dialdehydes

How could 1,4-butanediol be converted to 1,4-butandial (succinic aldehyde)? I thought of simple oxidation with CuO but apparently it yields gamma-butyryllactone according to erowid (https://erowid.org/...
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Oxidation of polycyclic aromatic compounds using KMnO4

How is tetracene oxidised by $\ce{KMnO4}?$ It appears that the product is a white solid with a benzene ring inside. What is the reaction mechanism? Is it radical based? Or does the $\ce{MnO4-}$ ion ...
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Tollens' test with beta hydroxy ketones

My book mentions that 1,5-dihydroxypentan-3-one will not give silver mirror with diammine silver(+1): This seems very counter intuitive to me as the alcoholic group can be easily oxidized to the ...
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1answer
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Names of NAD+ and NADH

As part of the biochemical process of glycolysis, NAD+ is reduced to NADH. In other words, nicotinamide adenine dinucleotide is reduced to... nicotinamide adenine dinucleotide? Everywhere I look ...
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1answer
106 views

Oxidation of Sodium Hydroxide in Ethanol?

So I read recently that: Alcoholic solutions of sodium hydroxide will oxidize in air, turning brown. First is this true? And if so what is oxidizing? I can't think of what sodium hydroxide ...
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268 views

Oxidation of 2-Methyl, 2-Phenyl Propane

Considering oxidation mechanism of side-chains in arenes, it is known that side-chains get oxidized to carboxylic group ($-COOH$). Below is a picture of 2-Methyl, 2-Phenyl Propane. When it gets ...
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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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1answer
334 views

Thermal decomposition of ester [closed]

I have a clear liquid with a faint sweet smell. I know this compound contains an aromatic group and an ester. However, something strange happens when I try to distill it - it forms a white solid. I ...
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1answer
195 views

Partial oxidation of toluene

While reading the preparation of phenol from cumene by reaction with $\ce{H2O2}$ or partial oxidation, I was curious to find out why toluene wasn't used. I checked the literature and found that ...
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Specific solvents for Wacker-Oxidation

I am currently working on a way to perform a Wacker oxidation of 1-Dodecene into 2-Dodecanone in a continous reaction where it flows through a benchtop NMR, which allows me to monitor the reaction ...
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How do I draw a curly arrow diagram for the oxidation of primary alcohol to an aldehyde and subsequently to a carboxylic acid? [duplicate]

I've determined the chemical equations for both the mechanisms, but I'm unable to draw curly arrow diagrams for the two reactions using potassium dichromate as the oxidising reagent. I'm not sure how ...
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Oxidation of diols using periodic acid

What are the orders of rates of oxidation with $\ce{HIO4}$ of the following diols? Explain with reasons. (a) $\ce{Me2C(OH)C(OH)Me2}$ (b) $\ce{Me2C(OH)CH(OH)Me}$ (c) $\ce{CH2(OH)CH2(OH)}$ (d)...
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202 views

Complete Oxidation of Methanol

I know that complete oxidation of primary alcohols produces acids: $$\ce{R-CH2(OH) ->[\ce{[O]}] R-CH(OH)(OH) ->[][-\ce{H2O}] R-CHO ->[\ce{[O]}] RCOOH}$$ I wonder if that is the case of ...