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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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Can iodometry analyse the peroxide radicals of palmitic acid after it has been heated?

I know that oleic acid in palm oil forms hydroxide radicals to form aldehydes in their secondary oxidation. Does a palmitic acid go under a similar process?
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Why does microplastic not decay faster in the oceans?

Microplastic — defined as plastic pieces smaller than 5 mm in diameter — is increasingly recognized as an environmental hazard. The small plastic pieces obviously last a long time in the ...
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1answer
58 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
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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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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
48 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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0answers
126 views

Mechanism for the oxidation of a secondary alcohol (with acidified KMnO4.

I'm doing an experiment soon where I have to oxidise 2-heptanol to 2-heptanone. The first part of the experiment involves a work up wherein I have to first add acid then my potassium permanganate ...
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2answers
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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
94 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
105 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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2answers
620 views

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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0answers
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Is photocatalysis of volatile organic compound always produce H, O, and C only?

I've read a journal about harvesting hydrogen from air pollutants (volatile organic compounds) with unbiased gas phase photoelectrochemical cell (ChemSusChem 2017, 10 (7), 1413–1418). I wish to ask ...
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2answers
211 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
137 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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0answers
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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1answer
149 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
83 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
496 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
289 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
687 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
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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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130 views

Is potassium ferricyanide a catalyst for the oxidation of luminol by hydrogen peroxide?

I have searched online on how potassium ferricyanide catalyses the oxidation of luminol by hydrogen peroxide. Apparently it reacts with hydrogen peroxide to produce oxygen. The oxygen then reacts with ...
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1answer
505 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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0answers
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How does sodium hydroxide dissolve flesh? [duplicate]

How does sodium hydroxide or bases dissolve flesh? I want to know mechanisms how sodium hydroxide dissolves our body protein.(or other organnic matters) Thank you in advance.
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1answer
116 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
705 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
322 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
273 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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162 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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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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1answer
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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
25k 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
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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
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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 ...