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 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 ...
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Will Laticrete's Spectralock 1 grout desilver a mirror's edges?

I make/sell mosaic mirrors. I'd like to use Laticrete's Spectralock 1 grout but I don't know if it will desilver the mirror's edges over time. I contacted both Laticrete and the mirror manufacturer to ...
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-1 votes
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reason for Popoff's rule [duplicate]

Popoff's rule, unless I'm mistaken basically states that when a chain containing a carbonyl carbon is oxidised, on fragmentation the carbonyl group(C=O) is retained by the smaller chain. Is there any ...
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3 votes
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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 ...
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2 votes
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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 ...
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1 vote
1 answer
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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{...
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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 ...
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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 ...
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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 ...
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2 votes
1 answer
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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 ...
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3 votes
0 answers
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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 ...
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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?
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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 ...
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1 vote
1 answer
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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 ...
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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 ...
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9 votes
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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 ...
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2 answers
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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 ...
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4 votes
1 answer
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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. ...
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2 votes
2 answers
124 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{...
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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 ...
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4 votes
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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 ...
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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?
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2 answers
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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 ...
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5 votes
1 answer
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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 $\ce{Cu2O}$....
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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 ...
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2 votes
1 answer
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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?
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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 ...
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0 votes
3 answers
719 views

How does copper oxidise alcohols?

Consider for example ethanol being heated in the presence of copper at 300 °C. How does it give ethanal as a product? Copper being in its elemental state (oxidation state 0). Since negative oxidation ...
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2 answers
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Major product in reaction of butan-2-one + selenium dioxide

When reading about $\ce{SeO_2}$ I read this following reaction: $\ce{CH3CH2COCH3 ->[SeO2] CH3CH2COCHO + CH3COCOCH3}$ In the following reaction it was stated that $\ce{CH3CH2COCHO}$ was the major ...
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4 votes
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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 ...
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2 votes
1 answer
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Periodic acid oxidation of carbonyls?

The following reaction seem to be valid; $\ce{CH2OH-CHOH-CH2OH ->[HIO4]CH2O + HCOOH + CH2O + 2H2O}$ Apparently, there are similar reactions by 2,3-dihydroxypropanal, and also by the straight chain ...
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1 vote
0 answers
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Nanocellulose suspension in water being dialysed in ethanol

I am working on nanocellulose. To prepare the sample for silanization, the first step is to dialyse the preparation in ethanol overnight. I wonder why this is a necessary step. Sorry, I am a physicist ...
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6 votes
0 answers
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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 ...
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1 answer
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Why is the molozonide adduct thermally unstable?

In the mechanism of alkene-ozonolysis, the intermediate molozonide adduct, which is a cyclical but symmetric molecule (shouldn't symmetry about the C-C single bond bring stability?), decomposes ...
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5 votes
1 answer
123 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-...
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0 votes
0 answers
435 views

What reaction is used for calculating pH of the solution obtained after ethanol oxidation with potassium permanganate?

If $\pu{30.0 ml}$ of $\pu{0.20 M}$ ethanol solution reacts with $\pu{1.80 g}$ potassium permanganate, what will be the final $\mathrm{pH}$ of the solution? Assume a complete reaction and that only the ...
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4 votes
1 answer
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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 ...
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3 votes
0 answers
288 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 ...
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2 votes
1 answer
94 views

Does CH3COOH + H2O (vinegar) lose its antibacterial and antiviral properties when exposed to air?

I have been reading about using CH3COOH + H2O (vinegar) as a mild antibacterial and antiviral agent. For example: https://pubmed.ncbi.nlm.nih.gov/15698693/ Note, before anyone gets confused (or ...
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10 votes
1 answer
327 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 ...
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1 vote
0 answers
48 views

What happens when unsaturated primary alcohol is reacted with acidic potassium dichromate? [closed]

It is clear that the hydroxy group in the substrate gets oxidised to carboxylic acid. But what happens to the double/triple bond in the unsaturated primary alcohol when it reacts with acidic potassium ...
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Which group will migrate in this BVG oxidation?

I know that H has a higher migratory aptitude order than phenyl. But, in this case, the phenyl ring has electron donating groups attached to it which enhances its migratory aptitude. So, which group ...
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2 votes
1 answer
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Why is potassium permanganate used to kill mollusks?

I know that potassium permanganate is used as a disinfectant for bacteria. Permanganate acts as a strong oxidizing agent that can rip the electrons off of bacterial cell membranes, resulting in a ...
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Counting electrons in Ozonolysis [closed]

I can't understand the electron count made on this page about Ozonolysis. (http://ursula.chem.yale.edu/~chem220/chem220js/STUDYAIDS/ozonolysis/Oz.html) This is the specific part of the article: From ...
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Relationship between microplastics and wildfire smoke [closed]

My understanding is that: microplastics are short fragments of previously long polymer chains; wildfire smoke largely consists of incompletely burned organic materials such as wood. Wood burns by ...
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0 votes
0 answers
152 views

Mechanism for oxidative workup of ozonide

Oxidative workup of ozonide produces ketone (in case both the substituents of carbon are alkyl groups) or carboxylic acid (in case one of the substituents is hydrogen), depending on the alkene. I have ...
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2 votes
1 answer
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Oxidation of alcohols by Ceric Ammonium Nitrate

I have realized that reaction with ceric ammonium nitrate essentially results in coordination of alcohol with $\ce{Ce(IV)}$ and my teacher referred that we should be able to proceed it to form ketone ...
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How do I get the smell of Febreeze (uncomplexed cyclodextrin composition) out of my carpet?

Help! I sprayed my old carpet, which had gotten a little mildewy from some wet towels left on it, with Febreeze original scent. Now I can't get that horrible scent out! It might also be mixed with ...
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Reaction of a cyclic tertiary alcohol with chromic acid

We know that $\ce{H2CrO4}$ cannot oxidize tertiary alcohols. The mechanism is: Now the ${\alpha}$ carbon does not have any hydrogen to proceed to next step. Therefore, this reaction would not occur. ...
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4 votes
2 answers
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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 ...
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