22
votes
Accepted
In what way could benzoin give Tollen's test?
Of your three "thoughts", you are correct that an aldol reaction is not an option. Not only is the product "crowded", but the reaction is reversible. [BTW, an aldol condensation occurs when water is ...
- 16.4k
13
votes
Accepted
Why might a prepared 1% solution of glucose take 2 hours to give maximum, stable reading on a glucometer?
Crystalline glucose is the alpha anomer, but the enzyme in the glucometer is specific for the beta form. They interconvert slowly in solution. See https://www.jofem.org/index.php/jofem/article/view/...
- 39k
12
votes
Accepted
Monoepoxidation of 1,2-dimethylcyclohexa-1,4-diene using m-CPBA
The interaction of the alkene with m-CPBA is primarily nucleophilic/electrophilic in nature, i.e. the π MO of the alkene attacks the O–O σ* orbital. Therefore, the more electron-rich alkene (i.e. more ...
- 71.1k
11
votes
How does steam prevent oxidation in tea leaves?
According to Tony Gebely at Tea Epicure (https://teaepicure.com/tea-leaves-oxidation/), it's not steam per se, but rather heating that slows oxidation, by denaturing two enzymes (polyphenol oxidase ...
- 12.1k
11
votes
Does Phenylacetylene undergo side chain oxidation with hot alkaline Potassium permanganate?
According to this source Chemistry Libre Texts
Alkynes, similar to alkenes, can be oxidized gently or strongly depending on the reaction environment. Since alkynes are less stable than alkenes, the ...
- 21.5k
10
votes
Identification of the organic compound
The given answer is wrong in many ways:
4 did not satisfy both criteria C and E, because it is not a chiral compound to begin with.
10 did not satisfy the criteria D, because it does give a ...
- 39.5k
9
votes
Accepted
Is cyclic ether oxidised by periodic acid?
Cyclic ethers usually do not get oxidized by periodic acid. However, epoxides would do only if they were acidified first or use acidified periodic acid in the reaction (Ref.1). In general, acidified ...
- 39.5k
9
votes
Accepted
Reaction of naphthalene with sodium dichromate/sulfuric acid
It depends on the reaction conditions.
I suspect the answer the question setter wants to see is phthalic acid, but the true answer is none of these. I have found multiple references (such as this US ...
- 21.5k
9
votes
Accepted
Does Phenylacetylene undergo side chain oxidation with hot alkaline Potassium permanganate?
Brief explanation
Hot alkaline solution of potassium permanganate oxidises a terminal alkyne according to the following process:
Triple bond between the first and second carbon atoms (they are marked ...
- 546
8
votes
Accepted
How to test for methanol?
Sorry @ JavaScriptCoder, but I've to agree with aventurin. I'd say idoform test should have been done in a certified laboratory because of safety concern. However, I think fractional distillation ...
- 39.5k
8
votes
What is the role of dichloromethane in the ozonolysis / Criegee oxidation?
Sometimes the solvent choice is very important to enhance or decrease reactivity of either of the reactants.
Dichloromethane is a widely used organic solvent. Chemists sometimes say tongue-in-cheek ...
- 67.3k
8
votes
Accepted
Partial oxidation of toluene
You can justify the formation of Benzaldehyde from Toluene by oxidising with peroxide just by looking at the mechanism of the reaction and think of migratory aptitude of Phenyl group , hydride and ...
- 5,593
8
votes
m-CPBA Selectivity between Baeyer Villiger Oxidation and Epoxidation?
The answer appears to be "it depends" (perhaps this should not surprise an experienced organic chemist).
According to the abstract of the paper by Mendelovici and Glotter [1] in steroid chemistry:
...
- 21.5k
8
votes
Accepted
Identification of the organic compound
I think that correct answer should be 5 and 6 only, because:
12 will produce terephthalic acid, instead of benzoic acid as it possess two benzylic-H (also given by 7).
4 and 10 doesn't satisfy ...
- 3,033
8
votes
How does copper oxidise alcohols?
When heated in air, a piece of copper metal gets oxidized into black copper oxide $\ce{CuO}$ according to $$\ce{2 Cu + O2 -> 2 CuO}$$
When hot copper oxide $\ce{CuO}$ is in contact with some ...
- 27k
8
votes
Definition of mineralisation in context of organic chemistry
Simply put: organic → inorganic. Mineralization is often also called TOC diminution (the term “TOC reduction” is purposely avoided due to ambiguity in chemical context). From Duffus et al. [1, p. 1263]...
- 37.4k
7
votes
What is the role of dichloromethane in the ozonolysis / Criegee oxidation?
Dichloromethane (DCM) is used in ozonolysis for inertness and it also gives ready access to easy work up through aqueous washing, from which it is easily separated normally containing the product(s).I'...
- 2,191
7
votes
Accepted
Mechanism of oxidative dearomatisation with hypervalent iodine
The conventional mechanism is as follows:
The phenol displaces one acetate group on iodine – this makes the iodine itself act as what is essentially a fancy leaving group. Nucleophilic attack at ...
- 71.1k
7
votes
Accepted
Epoxidation with peroxyacids
This source states that MCPBA gives preferential epoxidation of the more substituted alkene. This source explains that due to intra-molecular hydrogen bonding in solution, the high degree of ...
- 21.5k
7
votes
Accepted
Does the explosion of TNT include oxidation?
3 nitrogroups of TNT are rich of oxygen, but the aromatic ring has only carbon and hydrogen atoms.
Therefore oxygen of nitrogroups oxidizes carbon and hydrogen atoms.
There is no principle ...
- 39.1k
6
votes
Accepted
Product of oxidation of alkanes
Potassium permanganate, $\ce{KMnO4}$, is the most common and probably the most applicable oxidizing agent discussed in organic chemistry teaching classes. $\ce{KMnO4}$ is a very strong oxidizing agent,...
- 39.5k
6
votes
Accepted
Mechanism with hypohalite in haloform reaction
The mechanism of haloform reaction will also be almost similar in the case if we use hypohalites (here, it is $\ce{NaOCl}$).
In the first step, instead of $\ce{OH-}$, the acidic $\alpha$ proton will ...
- 5,593
6
votes
Is cyclic ether oxidised by periodic acid?
This quote is from Comprehensive Organic Name Reactions and Reagents by Zerong Wang.
The oxidation of adjacent diols with periodic acid or its salt in aqueous solution is generally known as the ...
- 4,312
6
votes
Combustion and oxidation
Combustion versus oxidation is not about what products are created, but about the way how they are produced.
Combustion is the kind of oxidation, usually using gaseous oxidant, sufficiently exothermic,...
- 39.1k
6
votes
Accepted
Combustion and oxidation
Apart from the fact that not all combustion involves oxygen (virtually everything combusts in chlorine trifluoride and oxygen doesn't come into it) the major difference is how far the reaction goes.
...
- 35.4k
5
votes
Mechanism of toluene oxidation with CrO3
The following mechanism is based on the findings made in The Mechanism of the Etard Reaction[1].
Reference:
(1) Necsoiu, I.; Balaban, A. T.; Pascaru, I.; Sliam, E.; Elian, M.; Nenitzescu, C. D. The ...
- 3,075
5
votes
What is the mechanism for the oxidative cleavage of diketones via permanganate under basic/hot conditions?
In J. Org. Chem. 1979, 44 (15), 2726–2730, the authors Lee and Chang have investigated the permanganate oxidation of alkynes to α-diketones. In addition, they investigated the oxidative cleavage ...
- 16.4k
5
votes
Accepted
Hydrogen peroxide and glycerol combination
If you want to ruin both reagents, then you can go ahead and mix them. Hydrogen peroxide oxidizes glycerol to various reagents. A possible reaction pathway can be depicted as follows (Ref.1):
This ...
- 39.5k
5
votes
Accepted
Mechanism of the reaction of cyclohexanol and concentrated nitric acid to form adipic acid
From the article by van Asselt and van Krevelen [1]:
Cyclohexanol is oxidized to cyclohexanone.
The cyclohexanone reacts with the nitrous acid to yield isonitrosocyclohexanone producing 2-nitro-2-...
- 364
5
votes
Accepted
Is aluminium foil pure aluminium?
From the Institute of Minerals, Materials and Mining,
Most aluminium foil is made from pure aluminium, but increasingly alloys are used to improve properties and reduce the thickness required.
...
- 168
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