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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68 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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Burnt/Oxidized Aluminium going invisible [closed]

I burnt an aluminium foil till I don't know if it's oxidized(AlO, Aluminium Oxide) or carbon molecules are formed on the surface, then submerged underwater then it turns invisible(the black(oxidized?) ...
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1answer
29 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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49 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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33 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
45 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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72 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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25 views

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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45 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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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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145 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 ...
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1answer
95 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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1answer
83 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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26 views

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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2answers
48 views

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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121 views

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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1answer
114 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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39 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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43 views

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
75 views

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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217 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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50 views

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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30 views

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
40 views

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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2answers
106 views

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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103 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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1answer
98 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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58 views

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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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
150 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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1answer
91 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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230 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
139 views

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
300 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
182 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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1answer
71 views

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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24 views

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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42 views

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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55 views

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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1answer
159 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 ...
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1answer
153 views

The oxidation of aldehydes and alpha-diketones with peroxy compounds

Recently, I have been reading up on the Baeyer-Villiger (BV) oxidation. The oxidation is most commonly discussed for ketones. However, the oxidation also works for aldehydes and $\alpha$-diketones (...
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1answer
443 views

Dependence of primary alcohol oxidation on presence of water and “strong” or “weak” oxidants

It is known that the oxidation of primary alcohols can result in aldehydes or carboxylic acids. The product obtained from the reaction is described as dependent on reagents and conditions;[1] "...
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3answers
523 views

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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Cross Cannizzarro reaction for ketones

I want to ask that cross cannizzarro could be possible between any aldehyde + ketone mixture(without alpha H) and we get products as aldehyde get oxidised and ketone get reduced(along with self ...
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1answer
46 views

Will fruits and vegetables be more oxidized if blended at high speed for a long time or at less rpm for a short period of time? [closed]

Will fruits and vegetables be less oxidized if blended at higher speeds for shorter periods of time, or at lower speeds for longer periods of time? Do the oxidized molecules in vegetable juice ...
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1answer
954 views

Side chain oxidation with KMnO4/H+

I know that in side chain oxidation with the given reagent follows oxidation of benzylic carbon (if atleast one benzylic hydrogen is present). So my answer would be But in my answer key only it is ...
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3answers
175 views

Is there a way to oxidize salicyl alcohol to salicylic acid without using chromium trioxide? [closed]

I'm doing a project for school and I need to convert salicyl alcohol to salicylic acid, but I'm not allowed to use $\ce{CrO3}$ because of its toxicity. I know it is also possible to oxidize a primary ...
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438 views

Mechanism of oxidation of phenol to quinone by chromium(VI)

In the supplementary information for Org. Lett. 2005, 7 (19), 4297–4300, the following experimental method for the synthesis of 2-bromo-6-methylcyclohexa-2,5-diene-1,4-dione is given: To a ...