Ch25: Anomeric Effect - Chemistry

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Chapter 25: Carbohydrates

The Anomeric Effect

In substituted cyclohexanes we learnt that the substituents usually prefer the equatorial position due to steric effects (review ?)
In rings containing O atoms and with adjacent electronegative substituents there is a preference for this substituent to be axial.
This is because of an electronic effect due to an interaction of the orbitals of the ring O and the substituent bond.
The anomeric center is important to the reactivity of carbohydrates because it is the site at which ring opening occurs, becoming the carbonyl group, the important functional group.

Study Tip:

The anomeric carbon or the anomeric center can be recognised by looking for the C that is attached to two O atoms by single bonds.