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11 votes

Is tropylium cyclopentadienide possible?

While I can't give a definitive disproof, my intuition is that an unsubstituted cyclopentadienide anion would be far too nucleophilic and react with the tropylium cation at non-cryogenic temperatures (...
Nicolau Saker Neto's user avatar
7 votes

Nomenclature of C6H5CO-O-NH2

According to the last printed version of Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book), the retained name hydroxylamine was used for the construction ...
Loong's user avatar
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7 votes

I left scented candles in a polypropylene container. How do I remove the smell?

The answer depends on (1) how patient you are (how much time you have), (2) how low a concentration of the offending substances you need to obtain, (3) whether you have someplace you can leave the box ...
Buck Thorn's user avatar
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6 votes

Why does the Wurtz-Fittig reaction occur?

The reaction follow either or both of following mechanism: Organo-Alkali Mechanism: When the aryl halide is reacted with sodium metal, an intermediate organo-alkali compound is formed, which is ...
Nilay Ghosh's user avatar
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6 votes
Accepted

Why does the Wurtz-Fittig reaction occur?

It is a question of randomization. Let's imagine that mixture of a moles of ArX and b moles of RX reacts with $\ce{Na}$. If the aryl halide Ar-X and alkyl halide R-X are reacting with about the same ...
Maurice's user avatar
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5 votes

Is the 4H-Pyran Cation aromatic?

As noted by Nicolau in the comments, this is really the pyrylium ion. It is usually drawn with a double bond to the oxygen atom, which then formally takes the positive charge. This allows an extra pi ...
Oscar Lanzi's user avatar
  • 59.9k
5 votes

Is there a symbol or representation for tolyl groups as there is for the phenyl group?

Yes there is Tol if I presume you refer to p-tolyl. See for instance page 16 of the author guidelines (revision December 2014) of the Encyclopedia of Organic Reagents initiated by Leo Paquette. On ...
Buttonwood's user avatar
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5 votes

Friedel-Crafts alkylation of fluorochloropropane

In the aforementioned question, Soumik Das has given acceptable reasoning (at least within our community, nobody has questioned his answer for five years). However, beside the fact that the Lewis acid ...
Mathew Mahindaratne's user avatar
4 votes

Why can't picric acid be made more acidic by adding nitro groups at the meta positions?

You can certainly make pentanitrophenol but it is way more harder to get the -NO2 group to occupy the last remaining m-places. Historically, it has been achieved previously in the early 1900s but the ...
Nilay Ghosh's user avatar
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4 votes
Accepted

Can a carbocation ever be more stable than a neutral molecule?

Yes this question is poorly stated, probably through no fault of the OP. (It looks like something from a textbook, in which case the authors of the book are to blame.) You can really compare only ...
Oscar Lanzi's user avatar
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4 votes
Accepted

How is nitrogen the most powerful electron donor in aromatic rings?

Nitrogen is able to donate its electrons to the aromatic pi-system more readily than oxygen and sulfur because its p-orbital (which contains the lone pair) is energetically closer to carbon (i.e., ...
Max Kallio's user avatar
4 votes

I left scented candles in a polypropylene container. How do I remove the smell?

The search terms I'd suggest are "accelerated off-gassing" and "plastic deodorization". Here is a search result that looks relevant: https://www.sciencedirect.com/science/article/...
piojo's user avatar
  • 337
3 votes

Which one has a greater dipole moment: benzamide or benzoic acid?

If you compare formic acid (1.415 D) and formamide (3.71 D) you note that the amide has the larger dipole moment, ie there appears to be a trend. If you add a ring it has a secondary (minor) effect of ...
Buck Thorn's user avatar
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3 votes

Aromaticity of chlorobenzene

To apply the $4n+2/4n$ rule at all is wrong unless the conjugated $\pi$ electrons are precisely in a single ring. In the first structure you drew that is true, and you can confidently count six $\pi$ ...
Oscar Lanzi's user avatar
  • 59.9k
3 votes

Is there a symbol or representation for tolyl groups as there is for the phenyl group?

Use tol as abbreviation for tolyl group. Ref.: https://www.axeleratio.com/ip/ligands/abbrev/IndexGrpLigAbbrev.htm
Nilay Ghosh's user avatar
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3 votes
Accepted

Non-catalysed exhaust gas

A much better tracer for leaks than toluene would be helium. Compared to toluene, helium is a noble gas and hence unlikely to react at the temperatures and presence of the catalysts in a converter. (...
Buttonwood's user avatar
  • 30.4k
3 votes

Is acetophenone a saturated compound?

This case explains a problem with using "saturated" versus "unsaturated". The boundary in real chemistry is not as distinct as the words would seem to imply because the behavior of ...
Oscar Lanzi's user avatar
  • 59.9k
3 votes
Accepted

How to neutralize the stink of decomposed fish?

The difference between fish hydrolysate and synthetic NPK is the world of plant beneficial microbes you are culturing and adding to the soil. Have those microbes work for you to reduce odour during ...
Lisa's user avatar
  • 46
2 votes

Why is the ortho isomer a major product in the nitration of toluene?

One other factor favoring the ortho isomer: hydrogen bonding. Yes, hydrogen bonding to the methyl group. Following the molecular orbital description of hydrogen bonding, an electron pair from the ...
Oscar Lanzi's user avatar
  • 59.9k
2 votes

Why is benzoic acid a stronger acid than 3-aminobenzoic acid?

3-Aminobenzoic acid exists as a zwitterion in solution (just like aminoacids, which the given compound is, just not natural) thus instead of existing as $\ce{C6H4(COOH)(NH2)}$ it exists as $\ce{C6H4(...
Kamal Koushik Duppalapudi's user avatar
2 votes

Aromaticity of a fused ring compound

The electron pair on the right is meant to be outward pointing in the plane of the atoms, not part of the pi system. If you had the electrons in the pi system, then the carbon would be attached to a ...
Oscar Lanzi's user avatar
  • 59.9k
2 votes

Does tropylium chloride exist in ionic form or does it exist as a covalent molecule?

The linked source in Mithoron's comment seems not to give a definitive answer, due to the instability/reactivity of the tropylium chloride/7-chloroheptatriene. We do know that hydroxy-tropylium ($\...
Oscar Lanzi's user avatar
  • 59.9k
2 votes

Why do halobenzenes not give Birch reduction?

Birch reduction of chlorobenzene has been achieved using gas-phase hydrated electrons $\ce{(H2O)_n^−}$, n = 30–65 leading to formation of a chloro-cyclohexadienyl radical $\ce{C6H6Cl.}$1. Birch ...
Nilay Ghosh's user avatar
  • 26.3k
2 votes
Accepted

1-Bromo-4-tert-butylbenzene reaction with NaNH2

The reaction will proceed by deprotonation of the benzene ring to give the benzyne, an unstable intermediate, which then will react with ammonia/amide anion to give a mixture of m and p t-butyl ...
Waylander's user avatar
  • 22.6k
2 votes
Accepted

Phenol reaction with nitration mixture

Yes, that's correct. Benzoquinone is one of the byproducts of nitration reaction and it occurs from oxidation. During the preparation of nitrophenols, by-products of oxidation, in particular ...
Nilay Ghosh's user avatar
  • 26.3k
1 vote

What test would give me a qualitative recognition of the presence of benzene in methylphenidate?

With my experience in Natural Products Chemistry, I think NMR is superior to any other method to identify a organic compound. And if you are a graduate student in any university you may get access to ...
Mathew Mahindaratne's user avatar
1 vote

Why is chlorine atom in chlorobenzene deactivating the benzene ring when it has M+ effect, which is stronger than I- in other cases?

Think about the lone pairs of halides. In case of fluorine, it is 2p-orbitals, in case of chlorine, it is 3p-orbitals and so on. Benzene, being an aromatic compound, interacts with electron-donating ...
jona173's user avatar
  • 567
1 vote

ease of dehydration

There are certain conditions we have to check before using the 4n rule to classify the compound as aromatic or anti-aromatic. One of the conditions required is that the electron density should ...
Sarah's user avatar
  • 21
1 vote

Why is o used for hydroxy groups in IUPAC naming instead of saying 2-hydroxy

Consider the two forms as dialects. With ortho (or o) you describe a 1,2 meta (or m) you describe a 1,3 para (or p) you describe a 1,4 relationship of two substituents of for instance a benzene ring....
Buttonwood's user avatar
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1 vote

How does the following cyclization reaction work?

Terminal to the alkyl chain, you have the motif of an acetal. In presence of aqueous acid, it can pass to hemiacetal and free aldehyde. From there, the aldehyde possibly is activated further by ...
Buttonwood's user avatar
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