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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 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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38 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
41 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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Using SF6 to prevent oleaginous nuts to turn rancid [on hold]

I am usually keeping nuts and various seeds in glass jars. I noticed that oleaginous nuts turn rancid after 6-8 months due to oxidation. I am wondering how much I can prevent oxidation by replacing ...
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1answer
49 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
41 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
58 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
33 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
219 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
68 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
144 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
52 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
79 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
182 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 ...
3
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1answer
146 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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0answers
178 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
1k 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
250 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
179 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
226 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
119 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
746 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
416 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
974 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
661 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
48 views

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
135 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 $\ce{H2CrO4}$ ...
6
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1answer
814 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
355 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
304 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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186 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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7k 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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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
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
41k 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
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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 ...