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Results tagged with organic-chemistry
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user 4945
Use this tag for questions relating to organic molecules and their properties (structure of organic molecules, spectroscopic properties, reaction mechanisms, stereochemistry etc). DO NOT use this tag as the only tag in your question, as this tag by itself cannot appropriately classify your question. Always use this tag in addition to other more specific tags.
1
vote
Accepted
Drawing formal charges/ lone pairs?
Ambiguity is the enemy of scientific communication. If things are up to interpretation, misinterpretation will happen, which will likely turn into errors down the line.
The chemistry teacher of a frie …
- 44.4k
11
votes
Accepted
Aromaticity of 1,4-Dioxin
Aromaticity is a fuzzy subject and there are no strict mathematical rules. There is no recognised unilateral theory that does explain it. This becomes a real issue when we are dealing with compounds t …
- 44.4k
3
votes
Why is carbon tetrachloride more stable than methane?
It is impossible to compare the stability of methane and carbon tetrachloride directly as the do not have a common frame of reference. At the same time you cannot claim that the dichlorine molecule is …
- 44.4k
3
votes
Keto-enol tautomerism in a bicyclo compound
Most of the times, the keto-tautomer is lower in energy than the enol-tautomer of a given compound. In all cases this is also very dependent of the actual conditions.
There are few cases, where the en …
- 44.4k
8
votes
How can I determine the size of tropolone molecule?
Since we're comparing: molden has a zmat builder and a force field (amber) implemented. You can start with the obvious choices of getting a structure from a database, or generating a starting structur …
- 44.4k
6
votes
Why is 1,2,3,4,5,8-hexahydronaphthalene more stable than 1,4,4a,5,8,8a-hexahydronaphthalene?
Disclaimer:
This post might be hard to read for some people. Some may even consider this a rant. You have been warned.
This answer will question the validity of the used models, as well as the basis f …
- 44.4k
7
votes
Accepted
How is resonance energy measured?
Resonance energy is a fictitious value, it cannot be measured, it is always only estimated. The definition in the gold book[1] clearly states this:
The difference in potential energy between the actu …
- 44.4k
8
votes
How to compare the acidity of this multicyclic hydrocarbon to the acidity of cyclopentadiene?
The method presented by Yusuf is a simplified model, which works best for well-behaved molecules. Unfortunately in this case it presents the 'correct' result based on incorrect assumptions. (Even thou …
- 44.4k
8
votes
Which biphenyl is optically active?
TL;DR: It's 2 (2,2'‐dibromo‐6,6'‐diiodo‐1,1'‐biphenyl) and maybe even 3 (2,2'‐diiodo‐1,1'‐biphenyl; 2,6‐dimethyl‐1,1'‐biphenyl) at higher temperatures.
Introduction
According to the IUPAC gold book …
- 44.4k
5
votes
What is the correct lewis structure of SCH⁻?
The ion in question is the deprotonated form of thioformaldehyde. While Lewis structures are in general not a very accurate way to depict the molecular structure, it should be made clear, that the mol …
- 44.4k
9
votes
Accepted
Stability of 4-pyridone vs 4-pyridinol
I don't think this is an either this or that situation. As with most of the equilibria we know it depends very much on the circumstances we look at it. Many examples of keto-enol-tautomerism are heavi …
- 44.4k
6
votes
Accepted
Why does coumarin predominantly exist in keto form?
The answer is as simple as it will be unhelpful to your original question: There is no tautomer possible.
Coumarin does not have a keto group, and there are no enolisable protons either. Coumarin co …
- 44.4k
5
votes
Which is the correct definition for metamers (or metamerism)?
There is no IUPAC definition for metamers or metamerism in the gold book (not even one that makes it obsolete), and Wikipedia doesn't even have a real article about it, see Metamerism.
In chemistr …
- 44.4k
5
votes
Can a molecule be achiral whilst it's resonance form chiral?
Unfortunately the sloppy depiction of sulfoxides will cause such misconceptions. Your analysis is quite good:
The central sulfur atom is bound to 3 atoms and then has a lone pair, so surely it has …
- 44.4k
6
votes
Accepted
What is the best hydrogen bond acceptor in 2-amino-N-(3-hydroxyphenyl)acetamide?
As a general rule of thumb, a nitrogen is usually a better hydrogen bond acceptor than an oxygen. There is a brief overview on Wikipedia with a couple of values and where they were derived from.
This …
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