# Questions tagged [chirality]

Applicable to questions about the ability of a molecule (or class of molecules) to be superimposed on their mirror image(s).

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### Do we need to check for all kinds of symmetry in a compound to declare it achiral?

I know that a compound is achiral if it contains any one of the following kind of symmetry. 1.Plane of symmetry 2.Centre of symmetry 3.Normal axis of symmetry 4.Alternate axis of symmetry It is ...
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### Type of chirality in polycyclic compounds

Ignoring whether or not this molecule could exist, is there a name for this type of chirality? This molecule's mirror image cannot be superimposed on itself but there are no chiral centres. Even ...
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### What reactants are suitable for testing flow based enantioselective catalysis? [closed]

Are there any simple and low cost reactants that normally forms racemic mixture that could be tested with a enantioselective catalyst to produce predominantly S or R results? The reactants should be ...
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### Why can't an “upside down” chiral molecule neutralize the polarized light effect? [duplicate]

Steve Mould did a nice video a few months back called "Why Sugar Always Twists Light To The Right" (link is timestamped at the critical part). However his explanation was not complete. He ...
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### Why has this molecule a S-chirality? [closed]

Can someone explain to me, why this molecule has an (S)-chirality? I don't get it. I tried to apply the rules, but I get only an (R)-chirality. Is there something special with cyclo-alkanes?
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### Number of chiral centers in penicillin V

I have often seen that in many drugs chirality plays a role. So I was trying to analyze the structure of Penicillin V. What is number of chiral centers in the structure of penicillin V? Is the ...
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### Which chiral carbon do L and D in L- or D-glucose refer to? [duplicate]

I see and D- and L- glucose are mirror images of each other. and I understand D and L are for chirality. But it is not clear which carbon do D and L refer to. Could anybody let me know? Thanks. What ...
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### Do different alkyl groups affect chirality?

I am a bit confused on the definition of a chiral center; A carbon atom is chiral if it has four different items bonded to it at the same time. source However I am not sure whether different alkyl ...
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### Are there reactions where the stirring direction would make a difference?

I'm not a chemist. I don't really do anything with chemistry, so I know little of the subject. I know a bit about chiral molecules. For example, I know that homochirality can affect light polarity. I'...
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### Can a chiral molecule be optically inactive?

Does there exist a chiral compound with zero optical activity? It seems possible that for some (chiral) arrangement of atoms, the optical activity of one section of the molecule could be exactly ...
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### Is nitrogen with 3 different substituents and lone pair a chiral center? Does it make the whole compound chiral too? [duplicate]

Is nitrogen considered a chiral centre or stereocenter when it has three different substituents attached to it along with a lone pair. By definition LG Wade says An asymmetric carbon atom is the ...
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### How is plane polarized light rotated by chiral compounds? [duplicate]

There are plenty of questions related to this topic on this site but no proper answer. Can anyone please explain to me how plane polarized light is rotated by chiral compounds, and why it cannot be ...
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### Identification of the organic compound

An organic compound A $(\ce{C10H14O})$ exhibits following characteristics. A) It reacts with metallic sodium to give a colorless odorless gas. B) It is oxidized by $\ce{KMnO4}$ to benzoic acid. C) It ...
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### QM9 dataset with chirality

I am trying to find chiral centers of molecules in QM9 dataset. Browsing their SMILES representation, I noticed SMILES yield using datasets.get_qm9(GGNNPreprocessor(), return_smiles=True) don't ...
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### Chirality as atom feature

I have been reading some literature on molecular energy prediction using machine learning techniques and I have noticed that one of the input parameters in many of the available models is "chirality". ...
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### Chirality in carbocations

The following compound is a carbocation. Clearly, the given compound does not have any element of symmetry. The compound is non planar due to the presence of ethyl group. Thus it must be chiral. But ...
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### Stereochemistry of C as non-chiral centre

When a C of a molecule is not a chiral centre, the spatial orientation of its substituent group doesn't affect its stereochemical specification, does it? Ex:
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### Priority of carbons attached to chiral group, one with double bonded oxygen, one with two oxygens [closed]

I have a chiral carbon. Two of the atoms attached to the carbon are other carbon atoms. One of those carbons has a double bonded oxygen and a methyl group attached. The other has two oxygens and a ...
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### Cahn–Ingold–Prelog Rules, cyclic structures, and breaking ties

(3S,5R)-3-ethyl-5-methylcyclohex-1-ene Does anyone know how one reaches the conclusion that the 5C is R? I tried using the Cahn–Ingold–Prelog priority rules but kept getting confused. From chem....
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### Chirality with tautomers

This molecule has 6 peaks in its proton NMR. I think this is due to the following tautomerisation: However, I am unsure as to whether this molecule would be chiral, as it can freely interconvert ...
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### Does a non-chiral substrate (2-bromo-2-methylpropane) also form two products via an SN1 mechanism?

If I have an alkyl halide, in which its tertiary carbon is non-chiral (for example 2-bromobutane), which reacts via an SN1 mechanism does it also produce 2 products? I am asking because I know that ...
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### Chiral carbon in carvone molecules

This is the structure of carvone, with the chiral carbon noted by *. I don't understand why this is a chiral carbon, to my understanding a chiral carbon is a carbon with 4 different chemical groups ...
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### How are these two molecules identical?

I can see that these compounds are identical as we have basically just done a 180 degree rotation of the molecules. But if we go by the concepts of chirality, the carbons 2 and 4 are chiral centers ...