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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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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 ...
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27 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?
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19 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 ...
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1answer
24 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 ...
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37 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 ...
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3answers
480 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 ...
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2answers
55 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 ...
3
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1answer
257 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. ...
2
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2answers
95 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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0answers
35 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 ...
4
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56 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 ...
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1answer
83 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?
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2answers
66 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 ...
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0answers
92 views

Does 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 $\ce{Cu^1+}$finally giving reddish brown precipitate of $\ce{Cu2O}$. ...
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72 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 ...
2
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1answer
55 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?
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63 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 ...
0
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3answers
169 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 ...
0
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2answers
86 views

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 ...
4
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1answer
62 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 ...
2
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1answer
151 views

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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0answers
15 views

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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62 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 ...
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1answer
92 views

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 ...
4
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1answer
81 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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205 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 ...
3
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1answer
30 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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0answers
87 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 ...
2
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1answer
66 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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1answer
285 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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0answers
47 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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0answers
21 views

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 ...
2
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1answer
88 views

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 ...
0
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1answer
71 views

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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1answer
36 views

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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0answers
84 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 ...
1
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1answer
669 views

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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0answers
63 views

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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0answers
82 views

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. ...
4
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2answers
864 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 ...
0
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1answer
101 views

Baeyer-Villiger Oxidation restricted to Ketones

According to Wikipedia, Baeyer Villiger oxidation occurs at the electron deficient oxygen site, with elimination of the carboxylate ion, and migration of an R group. But it is restricted to ketones ...
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0answers
69 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. ...
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0answers
249 views

Oxidation of ethanedioic acid with potassium permanganate

What are the products of the reaction of 1,3-butadiene with hot $\ce{KMnO4}$ (excess)? I know that $\ce{KMnO4}$ will first cleave the double bonds and we should get $$\ce{CH2=CH-CH=CH2 ->[KMnO4] ...
7
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2answers
756 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 ...
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2answers
66 views

Oven safe dessiccant?

Im sure there is a chemist/lab tech that knows a simple solution to my problem, as I cant seem to find a solution. When trying to strip and re-season cast iron cookware, I occasionally have problems ...
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1answer
503 views

Why do alkylarenes react with alkaline KMnO4, but not benzene? [closed]

Benzene($\ce{C6H6}$) does not react with alkaline $\ce{KMnO4}$, however alkylarenes react when there are benzylic hydrogens. What could be the reason for this? Thanks in advance
5
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0answers
136 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 ...
0
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2answers
593 views

Why can't we oxidise allylic alcohol to aldehyde using pyridinium chlorochromate? [closed]

I read in my book that we cannot use pyridinium chlorochromate (PCC). Why is that?
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2answers
2k views

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 ...
3
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2answers
69 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 ...