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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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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39 views

Mixtures readily oxidzing organic matter [on hold]

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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How to water with high oxidation reduction potential? [closed]

I'm looking for a process to maximize ORP (negative milivolts) with do-it-yourself methods. One way would be to use a reductor (electron donor) and simply dissolve it, other would be to use ...
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Why 2-hydroxytetrahydrofuran passes Tollen's test?

In FIITJEE's AIITS (an internal test series), I was asked to select the compound(s) which gives positive Tollen's test. And, 2-hydroxytetrahydofuran was an answer. So far, I know that Tollen's test ...
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Chemical Reaction Alternative to O2 Respiration in H2/N2 Atmosphere [on hold]

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
45 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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32 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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47 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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135 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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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
37 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
46 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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1answer
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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
59 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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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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1answer
28 views

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
67 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
62 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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1answer
91 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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95 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
126 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
76 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
54 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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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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69 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
79 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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167 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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1answer
181 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
41 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
649 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
110 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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319 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 ...
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1answer
59 views

C-4 oxidation of octanoic acid to 4-oxooctanoic acid

I am leading a project in which I am attempting to synthesize 4-oxooctanoic acid in a (mostly) biological pathway. Currently, I have reached a dead-end. I have a way to create octanoic acid through ...
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2answers
178 views

How does the human body deal with free radicals it creates itself?

I know that free radicals are created all over your body all the time as a byproduct of its chemical processes, (or maybe I do not and that is false). However I am confused about the distinction ...
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Rationalising diastereoselectivity of hydroboration using stereoelectronics

Using bulky reagents such as 9-BBN, hydroboration is often highly diastereoselective, giving rise to the 1,2-anti diastereomer: This is easily explained using a steric argument, with the major ...
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1answer
270 views

Organic reaction with Na2S2O4 [closed]

Question: In the first step due to cooperating Inductive and resonance effect C6H5N2 + will be attached at the ortho position of methyl group for which para position is occupied by Amine group ...
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1answer
270 views

Are secondary alcohols more easily oxidised as compared to phenol?

Which among the following compounds is oxidised most easily? 2-propanol ($\ce{CH3CHOHCH3}$) phenol ($\ce{PhOH}$) ethoxyethane ($\ce{Et-O-Et}$) 1-methyl cyclohexanol The answer given ...
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Reaction of cyclopropane with hot potassium permanganate

Hot potassium permanganate is usually used as an oxidising agent, and cyclopropane being an unstable three membered ring undergoes reaction with several reagents such as bromine, $\ce{HBr}$, metal ...
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Action of hot alkaline KMnO4 on tert butyl benzene

Side chain oxidation of aryl alkanes takes place if there is at least one alpha hydrogen present by all accounts I presumed that there would be no reaction. However the answer given was trimethyl ...
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309 views

What is the mechanism for the oxidative cleavage of diketones via permanganate under basic/hot conditions?

The products of the reaction are carboxylates. What exactly would cause the alkyne to cleave?
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318 views

Find product of the oxidation of 2-methylnaphthalene with chromium trioxide

This is a question from an organic chemistry book. I did not understand the solution given in that book. Here's the solution given in that book, I know that CrO3 oxidizes methyl group of toluene, but ...
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25 views

Why do we dip noble metals (Ir, Pd) into NaOH for an oxide coating in thermal oxidation?

I've noticed that a common technique for creating a layer of oxide onto palladium or iridium is to dip it into high concentrated NaOH prior to putting it in a furnace for ~800C. I've been reading ...
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414 views

difference between elimination reactions and oxidation reactions [closed]

I know that oxidation reactions involve the loss of hydrogen. But is the mechanism the same
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1answer
197 views

Why does 3-hydroxy-butan-2-one give positive Tollens' test?

Why does 3-hydroxy-butan-2-one give a positive Tollens' test despite the absence of an aldehyde group? What is the mechanism?
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1answer
1k views

Which alkene on heating with alkaline KMnO4 solution gives acetone and CO2?

Which alkene on heating with alkaline $\ce{KMnO4}$ solution gives acetone and a gas that turns lime water milky ? 2-methyl-2-butene isobutylene 1-butene 2-butene I know that $\ce{...