It has been mentioned that the two carbon atoms of a C__C double bond and the four atoms directly attached to them are all in the same plane and that rotation around the double bond is prevented. This means that in the case of a molecule WXC=CYZ, stereoisomerism exists when W X and Y Z. There are two and only two isomers (62 and 63), each superimposable on its mirror image unless one of the groups happens to carry a stereogenic center. Note that 62 and 63 are diastereomers, by the definition given on. There are two ways to name such isomers. In the older method, one isomer is called cis and the other trans. When Wผ Y, 62 is the cis and 63 the trans isomer. Unfortunately, there is no easy way to apply this method when the four groups are different. The newer method, which can be applied to all cases, is based on the Cahn–Ingold–Prelog system. The two groups at each carbon are ranked by the sequence rules. Then that isomer with the two higher ranking groups on the same side of the double bond is called (Z) (for the German word zusammen meaning together); the other is (E) (for
entgegen meaning opposite).218 A few examples are shown. Note that the (Z) isomer is not necessarily the one that would be called cis under the older system (e.g.,64, and 65). Like cis and trans, (E) and (Z) are used as prefixes; for example, 65 is called (E)-1-bromo-1,2-dichloroethene.
It has been mentioned that the two carbon atoms of a C__C double bond and the four atoms directly attached to them are all in the same plane and that rotation around the double bond is prevented. This means that in the case of a molecule WXC=CYZ, stereoisomerism exists when W X and Y Z. There are two and only two isomers (62 and 63), each superimposable on its mirror image unless one of the groups happens to carry a stereogenic center. Note that 62 and 63 are diastereomers, by the definition given on. There are two ways to name such isomers. In the older method, one isomer is called cis and the other trans. When Wผ Y, 62 is the cis and 63 the trans isomer. Unfortunately, there is no easy way to apply this method when the four groups are different. The newer method, which can be applied to all cases, is based on the Cahn–Ingold–Prelog system. The two groups at each carbon are ranked by the sequence rules. Then that isomer with the two higher ranking groups on the same side of the double bond is called (Z) (for the German word zusammen meaning together); the other is (E) (forentgegen meaning opposite).218 A few examples are shown. Note that the (Z) isomer is not necessarily the one that would be called cis under the older system (e.g.,64, and 65). Like cis and trans, (E) and (Z) are used as prefixes; for example, 65 is called (E)-1-bromo-1,2-dichloroethene.
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It has been mentioned that the two carbon atoms of a C__C double bond and the four atoms directly attached to them are all in the same plane and that rotation around the double bond is prevented. This means that in the case of a molecule WXC=CYZ, stereoisomerism exists when W X and Y Z. There are two and only two isomers (62 and 63), each superimposable on its mirror image unless one of the groups happens to carry a stereogenic center. Note that 62 and 63 are diastereomers, by the definition given on. There are two ways to name such isomers. In the older method, one isomer is called cis and the other trans. When Wผ Y, 62 is the cis and 63 the trans isomer. Unfortunately, there is no easy way to apply this method when the four groups are different. The newer method, which can be applied to all cases, is based on the Cahn–Ingold–Prelog system. The two groups at each carbon are ranked by the sequence rules. Then that isomer with the two higher ranking groups on the same side of the double bond is called (Z) (for the German word zusammen meaning together); the other is (E) (for
entgegen meaning opposite).218 A few examples are shown. Note that the (Z) isomer is not necessarily the one that would be called cis under the older system (e.g.,64, and 65). Like cis and trans, (E) and (Z) are used as prefixes; for example, 65 is called (E)-1-bromo-1,2-dichloroethene.
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