The Chirality of Adrenaline

external image adrenaline.jpg

Adrenaline contains one asymmetric carbon atom - the first carbon branched from the benzene ring. As we have learned in Chapter 5, an asymmetric carbon, or chiral center, is a carbon atom that is bonded to 4 different groups. The asymmetric carbon in adrenaline is bonded to H, OH, CH2NHCH3, and the 1,2-benzenediol.

If a compound contains one asymmetric carbon, it is chiral. Adrenaline is a chiral molecule because its mirror image is not superimposable. All chiral compounds must have an R and an S enantiomer. In adrenaline, the priority of the atoms attached to the chiral center is as follows, with the group containing the highest priority atom listed first: OH, CH2NHCH3, 1,2-benzenediol, and H. The priority of the atoms is determined by molecular weight. In R enantiomers, the first three atoms of highest priority are bonded in a clockwise order around the carbon. In S enantiomers, the atoms are bonded in a counterclockwise order.

In the experiments, a racemic mixture of adrenaline is used. A racemic mixture contains equal amounts of each enantiomer. A racemic mixture is optically inactive, and cannot yield an optically active product.

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