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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.
5
votes
Accepted
Why does the cyclization of open-chain glucose occur via the C5 hydroxyl group?
Due to the internal ring strain the best possible conformation is a six-membered heterocycle in this case called pyranose . A five-membered heterocycle may in rare cases also be formed, called furanos …
- 44.4k
3
votes
Accepted
Index of Hydrogen Deficiency for para-Toluenesulfonylchloride
You have to start from the general formula for the degree of unsaturation
$$DU = 1 + \frac{1}{2} \sum n_i(v_i-2),$$
where $n_i$ is the number of atoms with a valency of $v_i$.
For para-toluenesulfuny …
- 44.4k
2
votes
Accepted
What is an example of a biodegradable polyethylene?
In a short research I found little to no evidence, that a there is polypropylene/polyethylene, that can actually be called biodegradeable. I have found a couple of articles that have this as a topic. …
- 44.4k
2
votes
Why are tertiary carbon atoms of polymers more prone to photo-oxidation and -degradation?
This is admittedly a very brief and somewhat tempting answer and it might not be complete.
Photo-oxidation and -degradation occurs mainly via a radical mechanism. This is outlined on Wikipedia in mo …
- 44.4k
10
votes
Which platonic solids have been built as carbon skeletons?
There are the three painfully obvious platonic hydrocarbons: tetrahedrane, cubane, dodecahedrane.
The latter one also exists as a fullerene, i.e. $\ce{C20}$, which is also believed to be the smallest …
- 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 …
- 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
3
votes
Accepted
Generalizations regarding functional groups on benzene ring
Generalisation while often is a very useful tool at the zeroth approximation level, – that is crude, very crude, barely resembling the truth, – is a temptingly dangerous game to play. It often boils d …
- 44.4k
13
votes
Accepted
Is 1,2-dihydronaphthalene aromatic?
Hückel's rules are a very concise set of very strict rules. Most aromatic compounds do not comply with these.
Hückel (4n + 2) rule
Monocyclic planar (or almost planar) systems of trigonally (or …
- 44.4k
9
votes
Accepted
What is the major product of the reaction given?
Your reasoning is quite correct for an uncatalysed reaction.
I think you have forgotten about the hydrochloric acid you also add (in catalytic amounts). You will therefore protonate the double bond f …
- 44.4k
48
votes
Accepted
Why does cyclopropane react with bromine?
The following ring opening reaction will occour:
You are quite right about the angle strain. Because orbital interactions are not optimal in this geometry. Consider p-orbitals, then a natural bon …
- 44.4k
6
votes
Conformations of butane
Some years ago I did a (relaxed) rotational scan of n-butane for the purpose of showing that fatty acids are all-trans. That is also why I found the graph in Awesome's answer some kind of disturbing - …
- 44.4k
3
votes
Favorskii rearrangement
In extension to ron's answer, there are two reasons, why I think a $\ce{S_{N}2}$ reaction is unlikely to occur.
The LUMO, where the nucleophile will attack, of 2-Chlorocyclohexanone is the antibondi …
- 44.4k
6
votes
Accepted
SN1 reaction of ethanol at tertiary alkyl halide
Just to leave this question not unanswered. As ron already pointed out, you reasoning is correct. Based on the information given, the ethanol may perform a nucleophilic attack at the carbocation. To a …
- 44.4k
8
votes
Accepted
What are the most important resonance structures of 5-aminocycloheaxa-2,4-dienone?
The handwriting of your TA probably stems from ancient egyptian script, I had a hard time reading it. In the end I agree with jerepierre, interpreting it as "6E" or "8E" short for 6/8 electrons. The l …
- 44.4k