Q7-53E - Organic Chemistry (Mcmurry)

Question

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 E or Z configuration to the double bonds in both compounds.

Step-by-Step Solution

Answer

Tamoxifen will have Z configuration.

Clomiphene will have Z configuration.

Step 1: 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.

Step 2: 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.