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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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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
579 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
236 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
2k 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
678 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
2k 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
3k 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
1k 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
204 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
1k 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
472 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
518 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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0answers
229 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?
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0answers
9k views

Mechanism of toluene oxidation with CrO3

What is the mechanism for the following oxidation of toluene with $\ce{CrO3}$ in acetic anhydride? Use of chromic oxide ($\ce{CrO3}$): Toluene or substituted toluene is converted to benzylidene ...
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0answers
178 views

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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1answer
2k 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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0answers
2k views

Oxidation of alkenes by selenium dioxide to diketones

I know that $\ce{SeO2}$ readily affects the allylic position. The reaction mechanism of this reaction goes like this: (Source: Wikipedia; License: Public Domain) But, in my book, there's another ...
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1answer
1k views

Chromic acid oxidation of aldehydes and primary alcohols

The answer has to be both A and D. Chromic acid is a strong oxidizer and will take both aldehydes and primary alcohols to carboxylic acids. However the computer thinks otherwise. Am I just missing ...
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1answer
26k views

Can acidified or neutral KMnO4 oxidise toluene to benzoic acid?

Why is alkaline $\ce{KMnO4}$ used in the oxidation of toluene to benzoic acid? Can acidified or neutral $\ce{KMnO4}$ be used in this conversion?
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1answer
45k views

What is the mechanism for oxidation of ketones by the Popoff's rule?

Ketones are relatively much harder to oxidise, but they do undergo oxidation reactions at extreme temperatures. Our teacher also told us about Popoff's rule which states that, on oxidation of ...
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1answer
24k views

Mechanism of arene side chain oxidation by permanganate

When treated with hot, concentrated acidic $\ce{KMnO4}$, arenes are oxidised to the corresponding carboxylic acids. For example, toluene is oxidised to benzoic acid. I've tried to examine how this ...