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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46
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28k 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 ...
29
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1answer
4k 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 ...
20
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1answer
17k views

Migratory aptitude in Baeyer-Villiger reaction

In short, I do not understand how or why the migratory aptitude is as listed in every textbook I've read. Firstly, they talk about a positive charge being built up that is stabilised by the movement ...
16
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1answer
54k 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 ...
11
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131 views

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 ...
10
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1answer
291 views

How does steam prevent oxidation in tea leaves?

I recently started branching out into different "flavors" of tea. In this endeavor I've been learning more and more about different varieties of tea and was wondering if anyone could offer ...
10
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1answer
2k 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 ...
9
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3answers
507 views

Does Phenylacetylene undergo side chain oxidation with hot alkaline Potassium permanganate?

This question was asked in my book: To my knowledge, side chain oxidation with KMnO4 occurs only when a benzylic hydrogen is present. However this doesn't contain a benzylic hydrogen and hence ...
9
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3answers
9k 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 ...
8
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2answers
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m-CPBA Selectivity between Baeyer Villiger Oxidation and Epoxidation?

If both a ketone and an alkene are present in a molecule and you add one equivalent of m-CPBA, what are the factors that determine which group will be oxidized, the ketone through Baeyer-Villiger ...
8
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1answer
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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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779 views

Identification of the organic compound

An organic compound A $(\ce{C10H14O})$ exhibits following characteristics. A) It reacts with metallic sodium to give a colorless odorless gas. B) It is oxidized by $\ce{KMnO4}$ to benzoic acid. C) It ...
6
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2answers
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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 ...
6
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2answers
13k views

What is the role of dichloromethane in the ozonolysis / Criegee oxidation?

Why is $\ce{CH2Cl2}$ used in ozonolysis of alkenes and alkynes? What role does it play in the reaction? Is dichloromethane a common solvent for organic reactions and used for its inertness, or is it ...
6
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63 views

Mechanism for Ce(IV) Oxidation of Naphthalene

S. Cotton's Lanthanide and Actinide Chemistry reports that naphthalene can be oxidized to naphthalene-1,4-dione using cerric ammonium sulfate (CAS), $\ce{MeCN, H2SO4},$ and $\ce{H2O}$.1 No mechanism ...
6
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263 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?
5
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1answer
377 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) ...
5
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3answers
2k 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 ...
5
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1answer
200 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, ...
5
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1answer
338 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 ...
5
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1answer
28k 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?
5
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2answers
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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 ...
5
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What product will be formed from the side chain oxidation of 4‐ethyl‐1,1‐dimethyl‐3,4‐dihydro‐2H‐naphthalene?

Benzylic hydrogen is required for the side chain oxidation of benzene. But for this compound the top branch connected to the benzene ring does not have a benzylic hydrogen. So, will the top branch be ...
5
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71 views

How much oxygen is used up by the browning of an apple?

This is inspired by a recent popular question on Cooking. Let's assume that I take some apples, cut them up, and place them in a hermetically sealed container. Then the container goes into the fridge. ...
5
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137 views

Does periodic acid cleave acetals?

Recently, I started reading about the cleavage reactions done by $\ce{HIO4}$. I came across a statement which read $\ce{HIO4}$ can't cleave acetals but it can cleave hemiacetals. But when I tried to ...
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993 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 ...
4
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2answers
941 views

Oxidation of hydroxyl groups of glucose

In all oxidation reactions of glucose, it seems that the aldehyde group alone gets oxidised and none of the hydroxyl groups. In one reaction with nitric acid, the aldehyde group and the terminal ...
4
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1answer
69 views

On the molybdenum(III) oxide-catalysed oxidation of alkanes to carbonyls

The following reaction is specified in my notes; $$\ce{CH4 ->[Mo2O3, \Delta]HCHO}$$ The intermediate steps involve the dehydration of an alcohol to yield the final product. Wouldn't this only work ...
4
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1answer
82 views

TEMPO Radical Analogue

After investigating what makes the persistent radical TEMPO stable, I was wondering if another compound which is more feasible for my needs would be comparable to it. Would oxidizing 2,2’-dimethyl-...
4
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2answers
212 views

Chemical Reaction Alternative to O2 Respiration in H2/N2 Atmosphere [closed]

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 ...
4
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1answer
729 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 (...
4
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2answers
833 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?
4
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0answers
57 views

2-Iodoxybenzoic acid oxidation reaction

I was thinking about using 2-Iodoxybenzoic acid to selectively oxidize primary alcohols to aldehydes. I've found papers using various solvents like acetone/water mixture1, 2-methyl-2-propanol2, DMSO ...
4
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512 views

Reaction mechanism of thiol to disulfide oxidation under basic conditions?

I have been looking everywhere for an explanation to a reaction mechanism concerning the oxidation of DTT (or just thiols to disulfides in general) using oxygen as the oxidant. I'm aware that ...
4
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58 views

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....
4
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0answers
194 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 ...
4
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4k 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 ...
3
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3answers
12k views

How to test for methanol?

I wanted to make some ethanol from baker's yeast and I used sucrose. I've made it and put it in a glass jar. I left it on a warm place (near the radiator) until the yeast died and after they died I ...
3
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1answer
291 views

Reaction of naphthalene with sodium dichromate/sulfuric acid

I recently came across a question where naphthalene undergoes oxidation with sodium dichromate in presence of sulfuric acid. The given options were benzoic acid, phthalic acid, decalin, and tetralin. ...
3
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2answers
71 views

Oxidation to allylic alcohols without stoichiometric metal reagents

Common methods of oxidation of alkenes to allylic alcohols in one step usually use stoichiometric metal oxidants, e.g., sodium dichromate. Without using this type of reagent, are the other methods ...
3
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1answer
3k 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 ...
3
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1answer
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Action of KMno4/H+ and heat in this reaction

The first step uses LAH which is a hydride donor. So H- attacks any one carbonyl carbon and forms an aldehyde and acid attached to the ring. Then Conc. KMno4 is used. As far as i know, it cleaves c=c ...
3
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1answer
373 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 ...
3
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1answer
31 views

Degassing HI from Reaction (Via Ultrasound Maybe?)

I'm just going to put the questions first and the explanation after in case y'all don't have the patience. I want to know if it's reasonable to think that : Using an ultrasonic bath on something like ...
3
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1answer
295 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 ...
3
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1answer
602 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 ...
3
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0answers
37 views

How can the oxidation of TEMPO be selective?

According to the article "TEMPO oxidizes alcohols to aldehydes and ketones", the oxidation of TEMPO (2,2,6,6-tetramethylpiperidine-1-oxyl, 2564-83-2) can be highly selective. I assume it ...
3
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0answers
105 views

What's the chemical reaction between NaOCl and Brilliant Blue dye?

Based on my research NaOCl dissociates into Na+ and OCl-. Looking at the photo, how does the OCl- ion and the brilliant blue dye structure end up as the product? How does the OH attach itself to the ...
3
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1answer
1k views

Does Glycerol give silver mirror test with Tollen's Reagent?

I did an experiment in my school lab in which we had to identify the given organic compound. In my Lab Manual, it's written: Take 2 ml of Tollen's Reagent and add a few drops of organic sample. ...
3
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0answers
66 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) $\ce{MeCH(...