Quick Carbonyl Question

Edible

Hey, I need to know, can a carbonyl carbon which is singly bonded to two differenct alkyl groups be termed an assymetric carbon atom?
Cheers.

napapa

yes because the alkyl chains are of different length, whereas acetone is symmetric.

Mucco

I would say no, as it's planar and therefore has a plane of symmetry.
It can be deemed pro-chiral though, as the two faces of the carbonyl are different. This means that it's one step away from a chiral carbon, for instance, is you react it with a Grignard, you'll get two enantiomers.

The two faces of a carbonyl can be assigned by the CIP rules 're' and 'si'.

M

dirtyden

Its not chiral, it is prochiral, carbons with C2 symmetry are not chiral. As a previous poster pointed out either face of the carbonyl 'may' differentiate in a chiral enviroment and nuceophilic substitution may yield a chiral product.

Dave147

No, absolutely not.

napapa

I stand corrected. Apologies for misleading information, chirality was never my forte so shouldn't really comment on it. Thanks for correct explanation.