# Tag Info

17

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 eliminated from the initial aldol product. In the case of a benzoin aldol product, elimination of water is impossible.] Your second premise is a good one. ...

11

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 and peroxidase) that are responsible for it. Steaming is simply one way to do this: Much of the oxidation process revolves around polyphenols, particularly the ...

10

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 highly substituted alkene) preferentially reacts. With methyl groups there probably isn't too much steric hindrance. m-CPBA approaches above/below the alkene ...

10

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 precipitate with iodine in presence of $\ce{NaOH}$. That gives only 5 in given answer to satisfy all criteria. Let's eliminate given compounds in systematic order: ...

10

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 reactions conditions can be gentler. For examples, alkynes form vicinal dicarbonyls in neutral permanganate solution. For the alkene reaction to vicinal ...

9

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 periodic acid has been used as a qualitative test for the presence of epoxide moiety in organic compounds (Ref.1). The procedure is a modification of the ...

8

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 might be helpful for this identification (or simply verification). OP can do this at home since he/she has done simple distillation at home. Ethanol/water binary ...

8

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 that it can dissolve almost anything organic since it is rather mid-range in polarity. Other than that, it is also non-nucleophilic, non-electrophilic and ...

8

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 either the ortho or para position allows the loss of iodobenzene and another molecule of acetic acid. What I can't explain right now is why it chooses to go para ...

8

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: Treatment of 3β- and 3α-hydroxy-(acetoxy-)cholest-4-en-6-one and of 6β-and 6α-hydroxy-(acetoxy-)cholest-4-en-3-one with MCPBA gives two types of product, ...

8

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 statement C and D, as you've mentioned.

8

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 Patent and this Org. Syn prep) that refer to the production of naphthoquinones by oxidation of naphthalenes with high valent Chromium reagents under acid ...

8

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 in the figure above) converts into two carbonyl groups $\ce{C=O}$. The resulting molecule consists of a ketone part (blue) and an aldehyde part (red). The ...

7

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've not seen any evidence for it participating in the reaction. Alcohols react to form alkylhydroperoxides post ozonolysis. Toluene and acetonitrile can be ...

6

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 be taken up by $\ce{OCl-}$ (Remember, $\ce{HOCl}$ is a weak acid (but not as weak as water), so it's conjugate base i.e $\ce{OCl-}$ is a moderately strong base ...

6

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 methyl group. Firstly, if we delve into the mechanism of the oxidation of Cumene, we'll find that there is a rearrangement step in the mechanism. The ...

6

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 polarisation results in an electrophilic oxygen atom that adds to alkenes. The most substituted alkene will be the most electron-rich alkene and hence the most ...

6

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 Malaprade reaction. Several solvents have been used to increase the solubility of organic substrates and the reaction proceeds faster under acidic conditions. This ...

6

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 difference between oxidation and reduction agens being separate molecules, or being different parts of the same molecule. Note that TNT, in contrary to e.g ...

6

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, with a sufficiently high reaction rate. Characteristic combustion behavious is high temperature raise with thermal IR and light emission, frequently with ...

5

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 of several α-diketones to carboxylic acids. In the case of hexadecane-8,9-dione, permanganate oxidation under at least three sets of conditions provided ...

5

Here are the three equations describing the reduction of manganese (and concurrent oxidation of whatever substrate may be present) under basic, neutral and acidic conditions respectively. $$\ce{Mn^{+7}O4- +e- ->~ Mn^{+6}O4^2-~~~~[basic]}$$ $$\ce{2H2O + Mn^{+7}O4- + 3e- ->~ Mn^{+4}O2 + 4OH-~~~~[neutral]}$$ $$\ce{8H+ + Mn^{+7}O4^{-} + 5e- ->~ Mn^{+2} ... 5 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-nitrosocyclohexanone by reaction with nitric acid. With attendant ring opening and uptake of water the latter compound is transformed into 6-hydroxyimino-6-nitro ... 5 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. If you want to make sure that the Aluminium foil you're using is pure, the only way would probably to ask the manufacturer. Other than that, it could be the case ... 5 The selective Baeyer-Villiger Oxidation of unsaturated ketones is definitely depends on the conditions used. I do not want to eloborate this fact any further because it was well documented in Waylander's answer. Howevr, so far into the literature suggest that use of peracids in presence of unsaturation in the substrate ketone is not a good idea. The quote "... 5 The provided link (Lab Tutorial at Washington University in St. Louis) states the following: Another problem for water-treatment plants in the Great Lakes and Mississippi Valley is zebra mussels, which can "congregate" at the water intake and clog the screen, eventually sealing it off. Potassium permanganate, KMnO4, can be used to kill these ... 5 The above depicts a concept, rather than an equation for that there is no balance of atoms on the left and right of the arrow. Because if \ce{Mo2O3} is said to be used as catalyst rather than a (stoichiometric) reagent, then the oxygen in formaldehyde must be of different origin than \ce{Mo2O3}. On industrial scale, formaldehyde is prepared from ... 5 You likely had either or both of the following: Copper had some oxide on it, and this oxidized the alcohol leaving the metal behind. If there was air in your system, especially on heating copper could have reacted with it to generate the oxide (a relatively fast reaction with heating) and you're back to (1). The metal would then, of course, be available ... 5 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}$$When hot copper oxide \ce{CuO} is in contact with some ethanol vapor \ce{C2H5OH}, it reacts according to :$$\ce{CuO + C2H5OH -> Cu + CH3CHO + H2O} And the copper metal is regenerated. So if a copper plate is ...

5

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. In normal combustion (involving oxygen) the reaction is uncontrolled and tends to go mostly to completion (that is most things end up in their most ...

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