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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Does the acetic acid in vinegar oxidize significantly?

I apologize in advance for this question. I did very well in O Chem, but that was 50 years ago and I had to study very hard. I don't remember much of it now except what's common in basic biological ...
anongoodnurse's user avatar
2 votes
0 answers
33 views

Oxidation of 1,2 dicarbonyls by tollens reagent

According to the wiki page on Tollen's reagent https://en.wikipedia.org/wiki/Tollens%27_reagent#Qualitative_organic_analysis It also gives a positive test with hydrazines, hydrazones, α-hydroxy ...
mark's user avatar
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Why does hydrogen peroxide decompose during the oxidation of an aryl amine to and nitroarene (rt) and what are the possible overoxidation products?

Small scale: I attempted the oxidation of an aryl amine (2-amino-6-bromonaphtalene) to the nitroarene using hydrogen peroxide (ArNH2, H2O2, MeCN (15 mL as solvent). After trying it on small scale (0.1 ...
The Red Man Jolan Bonelli's user avatar
0 votes
0 answers
55 views

Mechanism of oxidation reaction with periodate

What is the mechanism of reaction of periodate with β-hydroxy amine? I tried the to write the mechanism similar to that of reaction with 1,2-diol but I am not able to obtain 2 carbonyl compound and ...
WIZARD GAMER's user avatar
1 vote
0 answers
60 views

Can I make an alcohol-based stain from a pigment with an alkaline extraction process?

I'm in a situation where I don't really even know enough to know if what I want makes sense or has the kinds of problems that I think it might have, but here's the situation: I would like to make a ...
nyckarna's user avatar
1 vote
2 answers
53 views

Oxidation of Isopropanol by Permanganate in Basic Solution

so I've been designing an experiment where I will explore the effect of isopropanol concentration on the colour change of a solution containing permanganate, isopropanol, and NaOH. I know that the ...
Brian Yu's user avatar
3 votes
0 answers
49 views

Can Schiff's reagent respond to hemiacetal?

Glucose responds with both Tollens' reagent $(\ce{AgNO3})$ and Fehling's solution $(\ce{CuSO4}).$ But it doesn't respond when treated with Schiff's reagent (p-rosaniline hydrochloride), the reason ...
znerd's user avatar
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-4 votes
2 answers
99 views

The Role of Acidified Potassium Manganate(VII) in Oxidation of Alcohols [closed]

The chemical equation for the oxidation of ethanol is given as: $$\ce{C2H5OH + 2[O] -> CH3COOH + H2O}.$$ Acidified potassium manganate (VII) solution $\ce{KMnO4}$ is added as the oxidising agent. ...
ZhangJin's user avatar
1 vote
0 answers
61 views

How does Tollen’s reagent reacts with hydroxylamine?

How does the Tollens' reagent react with hydroxyl amines? For example, let's consider phenylhydroxylamine $\ce{Ph-NH-OH}$ reaction with Tollens' reagent. First it yields $\ce{Ph-N=O}$ and on further ...
Aditya's user avatar
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Oxidation of substituted cyclic ketone using permanganate

From what I had learnt, reaction of this with $\ce{KMnO4}$ should give a dicarboxylic acid after cleavage of the carbon-carbon bond. But apparently this is the reaction that happens: Why is there a ...
AVS's user avatar
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-5 votes
1 answer
40 views

PH - Free Radical - O2 confusion [closed]

some context 1st, this is my understanding: I understand PH as the balance of protons vs electrons 7 being neutral, 1 being too many protons and 9 too many electrons. A free radical in the body as a ...
juanmf's user avatar
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1 vote
0 answers
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What's this reaction converting 9,10-dihydroanthracene into anthracene

I have no idea what this reaction converting 9,10-dihydroanthracene into anthracene is. Could someone help me with the name of the reaction/ or explain the mechanism of the formation of the product? 9,...
CarnotEngine's user avatar
3 votes
0 answers
46 views

How might humidity inhibit the drying or hardening chemical oxidation process of linseed-based oil paint?

I understand that linseed-based oil paint essentially dries or hardens by the chemical process of oxidation and not by evaporation. If it is possible that humidity somehow inhibits the chemical drying ...
Sketcher's user avatar
1 vote
0 answers
143 views

What reaction products are formed if an unsaturated fat is reacted at 20 - 50 °C with H2O2 of 35 %?

My question is: What reaction products are formed if an unsaturated fat is reacted at ca. 20 - 50 °C with aqueous hydrogen peroxide of ca. 35 %? To find the answer, we can subdivide the question into ...
IV_'s user avatar
  • 271
2 votes
1 answer
154 views

Oxidation Mechanism of A Peroxide reacting with a sulfide to form Anthracene

I have the following reaction: A peroxide reacting with a sulfide to form anthracene, sulfoxide and water or sulfoxide and water depending on the reactant. The reaction is from a paper discussing the ...
bobsburger's user avatar
1 vote
0 answers
152 views

Acetic acid reacted with Fehling's solution

During our experiment, we reacted acetic acid solution with Fehling's solution, expecting nothing to happen. Much to our surprise, the blue faded and the solution turned reddish-brown. Has this ...
Jono94's user avatar
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5 votes
0 answers
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Oxygen tolerant RAFT polymerization using AIBN?

I want to do some RAFT polymerizations but don't have a nitrogen line at the moment. It seems that people have recently implemented oxygen scavenging strategies to enable open-air RAFT polymerization. ...
toodles's user avatar
  • 137
-5 votes
1 answer
200 views

Does KMnO4 Oxidize Alpha-Beta Unsaturated Aldehydes? [closed]

I suspect that since $\ce{KMnO4}$ is a strong oxidizing agent it will react with the $\alpha,\beta$-unsaturated part of the carbonyl forming an epoxide. Are there any secondary reactions that one ...
TheBorcanu's user avatar
-1 votes
1 answer
73 views

Why is Quinone used, while oxidising primary alcohols by Oppenauer Oxidation, instead of Acetone? [closed]

Usually, during Oppenauer Oxidation, while oxidising secondary alcohols, acetone solution is used with Aluminium Tertiary Butoxide. This results into the oxidation of secondary alcohol into a ketone, ...
Enormity's user avatar
1 vote
1 answer
89 views

Hydroboration–oxidation reaction without THF

The first step of hydroboration–oxidation usually involves $\ce{BH3}$ accompanied by THF. Is it possible for hydroboration to occur without the presence of THF? Borane is incredibly reactive. Wouldn't ...
user28684's user avatar
9 votes
1 answer
695 views

Why might a prepared 1% solution of glucose take 2 hours to give maximum, stable reading on a glucometer?

I put 1.000g of glucose powder into a 1 L volumetric flask and filled the flask to the 1L line with room temperature distilled water. I then inverted several times for 10 minutes to mix until there ...
Joseph Hirsch's user avatar
1 vote
0 answers
73 views

Erythritol oxidation using acidified KMnO4

I have recently experimented with erythritol oxidation my primary aim was to make glyoxal. However regarding the nature and structure of erythritol several other side-products were also observed one ...
Copper Chopper's user avatar
4 votes
0 answers
180 views

Does acrolein give positive iodoform test?

Which of the following compound(s) give(s) a positive iodoform test? A. Acrolein B. Acetone C. Acetoacetic ester D. 2-Propanol According to me, the answer should be options B, C, and D as B is a ...
Vyom Joshi's user avatar
3 votes
1 answer
232 views

Definition of mineralisation in context of organic chemistry

What does it mean when an organic compound, say methylene blue, is said to be mineralised? An accompanied equation shows the dye being converted into carbon dioxide and oxygen. The only results I have ...
watermelonnn's user avatar
2 votes
1 answer
2k views

Oxidation of toluene, ethylbenzene and styrene with potassium permanganate in acidic medium

While I was studying my organic chemistry textbook, I came across the following reactions that need more clarifications: Oxidation of toluene (1) is the only reaction from the textbook, and I ...
donthababakka's user avatar
-4 votes
1 answer
723 views

Why does acetone give a positive test in Tollens test? [closed]

Tollens test is used to distinguish between ketones and aldehydes wherein it oxidizes aldehydes into a carboxylic acid (according to my textbook). However, another book says acetone gives a positive ...
blair's user avatar
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3 votes
0 answers
121 views

Troubleshooting synthesis of halazone from dichloramine-T

I was trying to oxidize some dichloramine-T to halazone. It should be easy enough since dichloramine-T has a free methyl group para to the para-sulfomyldichloro group. I followed a published procedure ...
Pulkit Sharma's user avatar
2 votes
0 answers
113 views

How does iodic(VII) acid oxidise amines? [closed]

What happens when 3‐aminobutan‐2‐one undergoes oxidative cleavage with $\ce{HIO4}?$ I'm particularly interested in the amine part. Would the hydroxy and amino groups on the same carbon be stable? Or ...
Umesh Konduru's user avatar
0 votes
1 answer
1k views

Does hot potassium permanganate break benzene rings?

Benzene rings are broken during ozonolysis, and alkenes treated with hot $\ce{KMnO4}$ undergo oxidative ozonolysis. So does that mean that the double bonds of benzene also are broken by hot $\ce{...
Mridul Kumar's user avatar
1 vote
0 answers
58 views

Chlorinated hydrocarbon destruction

What's a convenient method for lab-scale destruction of chlorinated hydrocarbons? Reductive dechlorination, total oxidation are fine as well as other routes you want to point out. If specific ...
Lorenzo Lami's user avatar
0 votes
0 answers
125 views

Do fats in edible oils and ghee undergo oxidation or rancidation when cooked in pressure cooker along with rice?

In a lot of dishes, it's quite common to cook rice along with fats like edible oil or ghee(clarified butter), in a pressure cooker. Now the pressure cooker can reach very high temperatures, to quickly ...
Profile name's user avatar
3 votes
0 answers
30 views

Are Wacker oxidations tolerant of carbonyl groups?

I was wondering if there was anything in the mechanism of a Wacker oxidation that would interfere with ketones or aldehydes already present in the molecule. Ketones and aldehydes can't be oxidized any ...
sweetandtangy's user avatar
2 votes
1 answer
123 views

Stereochemical outcomes for hydrohalogenation when there is a carbocation rearrangement

The following reaction is given: I want to be able to tell which of the following stereochemical outcomes are possible. I am aware that there are other possible products than the ones shown here ...
BlueMagic1923's user avatar
3 votes
0 answers
151 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 ...
Sam Lv's user avatar
  • 31
0 votes
0 answers
84 views

Side-chain Oxidation vs Oxidative Cleavage

When the above compound is subjected to acidified $\ce{KMnO4}$, can both side chain oxidation and oxidative cleavage of $\ce{C=C}$ bond occur? Or will one have priority over the other?
john's user avatar
  • 242
2 votes
0 answers
210 views

Oxidative cleavage of alkenes by Chromic Oxide

Does CrO3 (hot concentrated or acidified like Jones Reagent) cleave alkenes and alkynes like hot conc KMnO4 would, like this reaction? If not, why not? And do any other reagents other than Ozone ...
Hridai Khurana's user avatar
2 votes
1 answer
566 views

Reducing sugars and redox potential

I am wondering if reducing sugars are those that can act as reducing agents, and they act as such with Tollens and Fehling reaction, then what's the redox potential here? And is it a reversible ...
Luis's user avatar
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1 vote
0 answers
102 views

Differences in activated manganese dioxide synthesis

I've looked into preparations of activated manganese dioxide for some time now, and what confused me is the contrast between the original Attenborough method and some of the alternatives. A solution ...
steve d.'s user avatar
  • 323
9 votes
3 answers
2k 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 ...
Mia's user avatar
  • 123
-1 votes
2 answers
392 views

what happens if iron clamp is attached to a copper pipe to a wall? [closed]

I'm guessing its not a good idea, since iron will then corrode easily (also depending on the location and environment), Although copper do not rust it will increase the rate of it from oxidizing. plus ...
Khrizielle Castro's user avatar
4 votes
1 answer
3k 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. ...
Cyclopropanol's user avatar
2 votes
2 answers
391 views

Synthesis of active chemical manganese dioxide (CMD) for primary alcohol oxidation

This paper1 uses chemical manganese dioxide (CMD) instead of activated manganese dioxide for mild alcohol oxidation. I'm looking for a route on how to synthesize active CMD. Could this work? $$\ce{...
steve d.'s user avatar
  • 323
1 vote
0 answers
43 views

Does HIO4 cleave hemiacetals? [duplicate]

I had written in my notes that it does. But I can't find any credible source for it. A simple Google search only brings up this old and unanswered question. The questioner failed to specify the source ...
Ranjeet Mishra's user avatar
4 votes
0 answers
158 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 ...
steve d.'s user avatar
  • 323
1 vote
1 answer
178 views

Can dimethyl sulphide be used for ozonolysis of benzene?

There is literature that suggests that ozonolysis of benzene occurs with ozone and $\ce{Zn/H2O}$. Can it take place with ozone and dimethyl sulphide?
Anshu Apoorva's user avatar
1 vote
2 answers
377 views

Combustion and oxidation [closed]

What is the difference between combusting and oxidizing? Oxidation of alcohols leads to formation of aldehydes and carboxylic acid whereas the combustion of alcohols leads to the formation of carbon ...
Lime's user avatar
  • 41
5 votes
1 answer
2k views

Do formaldehyde and ethylene glycol give positive Fehling's test?

Fehling's test follows a single electron transfer mechanism, with electron transfer form the substrate to $\ce{Cu^2+}$, which forms $\ce{Cu^+},$ finally giving reddish brown precipitate of $\ce{Cu2O}$....
sameed hussain's user avatar
6 votes
0 answers
111 views

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 ...
john's user avatar
  • 242
2 votes
1 answer
372 views

Why is the silver salt ammoniated to form the Tollen's reagent? [duplicate]

When doing a distinguishing test between aldehydes and ketones using Tollen's reagent, is it necessary to convert $\ce{Ag+}$ ions into $\ce{Ag(NH3)2+}$ in order to oxidize the aldehyde?
john's user avatar
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1 vote
0 answers
70 views

Reaction of Tollen's reagent with 7‐oxabicyclo[2.2.1]heptan‐1‐ol

Identify whether the given compound will get oxidised by Tollen's reagent. The problem here is with the bridged alpha carbon. It cannot pertain sp2 character in the middle of the reaction as it is ...
Abhishek P's user avatar