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Magazine Chapter 7: Q7-53E (page 219)
Tamoxifen, a drug used in the treatment of breast cancer, and clomiphene, a drug used in fertility treatment, have similar structures but very different effects. Assign Eor Zconfiguration to the double bonds in both compounds.
Short Answer
Tamoxifen will have Z configuration.
Clomiphene will have Z configuration.
Step by step solution
Definition of E and Z configuration
When the same priority groups are adjacent to each other, then the alkene are termed as Z configuration
Similarly, when the same priority groups are opposite to each other, then the alkene termed as E configuration.
Assigning configuration to Tamoxifen
The benzene ring will have greater priority than the alkyl group.
Among the phenyl group, the substituted phenyl group will have greater priority.
Hence, Tamoxifen has Z configuration.
Structure of the given compounds with the configuration is given below.
2: Assigning configuration to Clomiphene
Since chlorine has a higher atomic number than carbon, chlorine will be given first priority. Among the phenyl groups, the substituted phenyl group will be given greater priority.
Hence, clomiphene has Z configuration.
Structure of the given compound with the configuration is given below.
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