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Please explain in detail about Pseudo chiral carbon and its applications in organic chemistry

Please explain in detail about Pseudo chiral carbon and its applications in organic chemistry

Grade:12

4 Answers

Chetan Mandayam Nayakar
312 Points
10 years ago

Pseudo-asymmetric Carbon Atom

The traditional name for a tetrahedrally coordinated carbon atom bonded to four different entities, two and only two of which have the same constitution but opposite chirality sense. The r/s descriptors of pseudo-asymmetric carbon atoms are invariant on reflection in a mirror (i.e. r remains r, and s remains s), but are reversed by the exchange of any two entities (i.e. r becomes s, and s becomes r). An example is C-3 of ribaric (C-3 is r), xylaric acid (C-3 is s) or hyoscyamine (C-3 is r). The hyphen in pseudo-asymmetric may be omitted.

 


ribaric acid xylaric acid


hyoscyamine

 

Godfrey Classic Prince
633 Points
10 years ago

Dear Sanatan Vatsa,

Pseudo Asymmetric Chiral Carbon, the traditional name for a tetrahedrally coordinated carbon atom bonded to four different entities, two and only two of which have the same constitution but opposite chirality sense.
The r/s descriptors of pseudo-asymmetric carbon atoms are invariant on reflection in a mirror (i.e. r remains r, and s remains s), but are reversed by the exchange of any two entities (i.e. r becomes s, and s becomes r).

For more idea please visit the following page given below

http://old.iupac.org/goldbook/P04921.pdf

 

Hope this helped you immensely..

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rahul malik
19 Points
4 years ago
The atom which changes from chiral centre to achiral centre by the change in its configuation is known as psuaedo chiral centre.
conditions for psuedo chiral centre is :
1: that atom should be bonded with 2 different groups
2:atom should be bonded with 2 identical chiral centres or 2 double bondsthat can show G.I{geometrical isomerism}
ankit singh
askIITians Faculty 614 Points
one year ago

Well what I know is a Pro Chiral Carbon. But with the given name "Pseudo", it seems both are same.
Such a carbon atom that is not Chiral initially, but becomes Chiral after the attack of a my reagent is called a Pro Chiral Carbon.
Consider the case of a tertiary butyl free radical, with the form as -

CH(3)---C---CH(2)-Cl
|
CH(2)-F
If you perform Bromination in the presence of sunlight, then a Br group attaches to the free radical carbon, in super controlled conditions.
In such a case, as you can see, the compound in initially not Chiral but after reaction becomes Chiral.
This is what we call pro chiral carbon or pseudo chiral carbon.

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