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.

Filter by
Sorted by
Tagged with
-1
votes
1answer
75 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
2
votes
0answers
33 views

Why doesn't HIO4 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 ...
-1
votes
0answers
38 views

Why Triple bond should not be placed at terminal carbon of Alkyne? [closed]

In Hydrogenation of Alkynes (eg like Lindlar or Birch reduction) it is said that, Triple bond shoudn't be attached to terminal carbon of alkyne. Why it is said like this ?
-1
votes
2answers
58 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?
9
votes
2answers
261 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
votes
2answers
33 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 ...
2
votes
0answers
30 views

What is the order of adding chemicals in Hummers method for graphite oxide?

I am trying to make graphene oxide but failing miserably. The XRD peak is at 24 (2θ) instead of being near 10. Raman shows correct g and d peaks but are not very sharp. The colour of the end product ...
2
votes
0answers
62 views

What is the product of following iodoform reaction?

Question Attempt I think the product A would be as I have attempted below, but I am getting the answer as A but book says D. Where am I wrong? Please help.
0
votes
1answer
71 views

2-Methylpropan-2-ol and Iodoform test

Can 2-methylpropan-2-ol be converted into methyl ketone the action of $\ce{I2}$ in the presence of alkali base and thus give iodoform test? Answer given to this question is that it can't give ...
1
vote
0answers
48 views

Mechanism of alkene dihydroxylation with potassium permanganate

I have scavenged the internet for different mechanisms for permanganate-mediated alkene oxidation and have found satisfactory mechanisms for oxidative cleavage and dihydroxylation under basic ...
0
votes
1answer
66 views

Reaction of 1,2-diketones with periodic acid [closed]

$\ce{HIO4}$ can oxidise alcohols. But does $\ce{HIO4}$ undergo any reaction/act as oxidant with 1,2-diketones?
0
votes
1answer
38 views

Chirality and number of sterioisomers

I have recently read that the number of sterioisomers in a compound having n chiral centres is 2^n. (That is, if no meso form is present) The below question asks for the number of sterioisomers in ...
2
votes
1answer
207 views

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 ...
-4
votes
1answer
47 views

Organic chemistry [closed]

Could someone tell me what happens when a compound having a benzene ring reacts with a mixture of NaOH/HCHO? What reaction and mechanism does this follow?
-1
votes
1answer
62 views

Do all anhydrous organic matter burn? [closed]

All organic matter seems to be inflammable when dried up. Petroleum, Alcohol, Wood, and Coal burns readily. Can I call it a general rule? Are there known exceptions? What makes them the exceptions?
1
vote
0answers
15 views

Residue from biomass incineration [closed]

What gasses are typically produced when biomass is incinerated at high temperatures (600 C) in high oxygen environments and what is a typical composition of the ashes left behind?
0
votes
0answers
54 views

Does an aryl compound with any functional group attached to it, undergo benzylic oxidation? [duplicate]

> If you look at this compound, only the benzylic carbon on the top has a hydrogen attached to it, so how do we oxidize only the top part without touching the lower one (not sure if this product is ...
0
votes
0answers
16 views

Is there any way of testing antioxidant ability of different substances?

For my investigation, I am looking at the antioxidant levels of different types of tea. How could I compare the antioxidating ability of each tea? For example, I know there is a method calling for ...
1
vote
1answer
228 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. ...
0
votes
2answers
87 views

Is aluminium foil pure aluminium? [closed]

Is aluminium foil pure aluminium? Or does it have other elements in the e.g: tin (Sn) or lead (Pb)? Because when I try to oxidize it through the process of submerging it in water, it doesn't look like ...
2
votes
1answer
46 views

Converting cyclic compounds to their corresponding aliphatic compounds

Is there any reaction available to convert cyclic compounds to their corresponding aliphatic compounds? eg. Converting cyclohexane to n hexane
2
votes
1answer
87 views

Why glucose and other similar carbohydrates are oxidised fully by HIO4?

$\ce{HIO4_{(aq)}}$ requires the vicinal diols to have syn configuration, as it forms a cyclic periodate ester. But glucose does not have syn configuration at C3, and if you consider cyclic forms of ...
1
vote
0answers
38 views

Oxidation of ascorbic acid (Vitamin C) [closed]

What would you suggest me to use for oxidation of vitamin C to dehydroascorbic acid instead of bromine water?
-1
votes
1answer
103 views

Mechanism of the reaction of cyclohexanol and concentrated nitric acid to form adipic acid [closed]

If someone could please give me the hint to how the initial attack is carried out, it'd be a huge help.
0
votes
1answer
200 views

What is the oxidation state of copper in Gilman's Reagent? [closed]

What is the oxidation state of copper in Gilman's reagent? In $\ce{R-Cu}$ bond the oxidation state is +1. Thus in $\ce{R-Cu-R}$ bond the oxidation state has to be +2. But if that so why positive $\ce{...
0
votes
0answers
68 views

What exactly is an 'activated' alcohol? Benzylic vs. Allylic vs. Aliphatic

I'm currently writing a report about the oxidations of various alcohols using different catalytic systems. In all papers it is stated that benzylic and allylic alcohols are "activated", while ...
2
votes
0answers
53 views

Do tertiary ethers tolerate oxidative workup of an ozonolysis reaction?

I am attempting to cleave a double bond into a carboxylic acid and carbon dioxide using an ozonolysis reaction followed by an oxidative workup. I am concerned with the presence of a tertiary ether in ...
1
vote
0answers
51 views

Rate determining step in oxidation of alcohols using chromium-related compounds

I wanted to ask a question about the kinetics of an oxidation reaction using chromium reagents. I was given a lecture today on the mechanism of alcohol oxidations using Chromate (VI) reagents: My ...
0
votes
0answers
402 views

Oxidation of certain acids by potassium permanganate

Why does potassium permanganate oxidize formic acid and oxalic acid, but has no reaction with benzoic acid and acetic acid? The reactions were heated in a water bath (~70-80 °C). Oxalic acid had ...
-1
votes
1answer
169 views

Do secondary alcohols react faster than primary alcohols or is it the other around? [closed]

My questions is that do secondary alcohols react faster than primary alcohols or is it the other around? This for the oxidation of the alcohol to a ketone or an aldehyde. This reaction is with KMnO4 ...
4
votes
0answers
175 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 ...
1
vote
1answer
93 views

Does the explosion of TNT include oxidation?

This comment below the question Rocket explosion compared to kT of TNT; has one ever knocked something over at a distance? suggests that ...TNT includes it's own oxidizer... Explosion isn't the ...
2
votes
0answers
26 views

Can an alcohol oxidation to ketone happen with hydrogen peroxide? [duplicate]

As far as I know, usually $\ce{CrO3}$ and $\ce{KMnO4}$ are used for this scope, but can other oxidizers such as $\ce{H2O2}$ be used?
4
votes
0answers
47 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....
1
vote
2answers
54 views

Mixtures readily oxidzing organic matter [closed]

Are there other mixtures than piranha solution with similiar or better ability to completely and readily oxidize organic matter? Perhaps peracetic/performic acid?
4
votes
2answers
136 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 ...
1
vote
1answer
195 views

Usage of TFA in Pfitzner-Moffat oxidation and Collins vs Jones oxidation

Is the addition of TFA in Pfitzner-Moffat oxidation to protonate the DCC to form a positive carbocation for the alcohol to attack? Or is there more to it? Why is TFA used and not other acids? Are ...
0
votes
0answers
49 views

Last steps of mechanism of Swern Oxidation

My question is regarding Swern oxidation. Why is the methyl group of the DMSO deprotonated and not directly the red hydrogen atom of the R2-CH-O bond deprotonated? Shouldn't it be that oxygen more ...
2
votes
0answers
64 views

Equivalents Triethylamine in Swern-oxidation

Hey folks, so I've been wondering why the use of 5 equivalents of Et3N in this case of a Swern-oxidation is necessary. I have done this reaction succesfully quite a few times now, but all the ...
2
votes
1answer
112 views

Reaction between 1-methylcyclopentanol and potassium permanganate

In my basic organic chemistry class, I learned that only primary and secondary alcohols undergo oxidation (using $\ce{KMnO4}$). However, what is the outcome of reacting tertiary alcohol (1-...
6
votes
2answers
576 views

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 ...
0
votes
0answers
61 views

Oxidation of Aromatic Methyl to Aldehyde by CAN

I read in my text that Ceric Ammonium Nitrate is used for oxidation of primary alcohols. But the surprising part was that, according to the book, it could oxidise aromatic methyl group to a -CHO group....
2
votes
0answers
31 views

Why is the titratable acidity of my wine going down as it ages and oxidises?

I am currently studying chemistry in grade 12 studies and I have come across a halt in my investigation. The experiment was to see how the increase in ethanol would lead to a more acidic wine, ...
5
votes
1answer
93 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, ...
2
votes
2answers
151 views

What reagents or series of reactions would allow for selective hydroxylation of an allylic methyl group outside of a ring?

Sample transformation for selective hydroxylation of an allylic methyl group outside of a ring. Selenium dioxide would not work since hydroxylation would be favored inside the ring.
1
vote
1answer
140 views

Cheap but efficient disinfectant / biocide for home lab

EDIT I am forced to reword my question about a chemical mixing ratio. I have seen in Wikipedia that peroxide ($\ce{H2O2}$) and Acetic Acid can be mixed to Peracetic acid - this is an equilibrium. I ...
3
votes
1answer
123 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 ...
1
vote
0answers
74 views

Oxidation of diols to dialdehydes

How could 1,4-butanediol be converted to 1,4-butandial (succinic aldehyde)? I thought of simple oxidation with $\ce{CuO}$ but apparently it yields gamma-butyrolactone according to erowid and this ...
3
votes
1answer
127 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 ...
1
vote
1answer
337 views

The products of a chain reaction beginning with acetone and sodium amide

I encountered the following question in an exam: $\ce{CH3COCH3 + NaNH2}$  giving out $\ce{A}$. $\ce{A}$ then reacts with $\ce{C2H2}$ giving out $\ce{B}$. $\ce{B}$ then reacts with $\ce{H+}$ to ...