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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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How to determine which liquid has higher antioxidant content?

If I have two solutions with me and I want to find out which one has a greater antioxidant content then how can I experimentally find that out in a laboratory? What are the chemical reactions? The two ...
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Oxidation of aldehydes and ketones [duplicate]

Why presence of alkyl group in make ketones very hard to oxidize whereas presence of H atom makes aldehyde easy to get oxidized?
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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
35 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
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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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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
47 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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32 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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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
61 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
54 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
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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
82 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
76 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
64 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
52 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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32 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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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
53 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
61 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
118 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
132 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
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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
537 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
103 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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0answers
271 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
57 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
159 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
238 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
249 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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236 views

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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2answers
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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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2answers
292 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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1answer
269 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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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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1answer
347 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
161 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{...
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1answer
538 views

Can methanol be oxidised by PCC?

Pyridinium chlorochromate (PCC) in $\ce{CH2Cl2}$ can be used to oxidise primary alcohols only to aldehydes. I can't however, find any reference of it oxidising methanol (which is strictly speaking not ...
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1answer
1k views

Reaction of ethylene glycol with acidified potassium permangnate

One would expect the reaction of ethylene glycol with acidified potassium permangnate to result in oxidation of ethylene glycol to oxalic acid. But a Q&A guide book tells me it is oxidized to ...
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1answer
2k views

Do aldehydes give bromine water test? [closed]

If they give bromine water test, what do they form? I think that aldehydes will get oxidised and so decolourise bromine water but I don't know if that happens in normal conditions.
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1answer
965 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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1answer
163 views

Are allylic three degree alcohols oxidized by the Jones' reagent via a classical carbocation intermediate?

I know the mechanism for Jones' oxidation is (picture from Organic Chemistry by Clayden): and it proceeds through a chromate ester. And in general we understand that the Jones' reagent $\ce{H2CrO4}$ ...
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1answer
946 views

Monoepoxidation of 1,2-dimethylcyclohexa-1,4-diene using m-CPBA

What is the product formed when 1,2-dimethylcyclohexa-1,4-diene undergoes epoxidation with one equivalent of m-CPBA (meta-chloroperbenzoic acid)? In the epoxidation mechanism, the π-electrons ...
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2answers
402 views

What is the mechanism for the oxidation of a lactol to a lactone?

Recently, I came to know that lactols can be converted to lactones but I wasn't able to find the suitable reagent and the reaction mechanism. Can someone elaborate the same?
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1answer
380 views

Are PCC and Collin's reagent completely identical in their oxidizing action?

Are PCC and Collin's reagent completely identical in their oxidizing action? Is there any advantage (or disadvantages) over the other?
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207 views

Reaction of fumaric acid and performic acid

Performic acid ($\ce{CH2O3}$) has strong oxidizing properties. So when it reacts with fumaric acid, is this the product (2,3-dihydroxybutanedioic acid) that I should expect?