8-32c - Organic Chemistry (Mcmurry)

Question

Which of the reactions below would result in a product mixture that would rotate plane-polarized light?

c) 

Step-by-Step Solution

Answer

The product mixture of this reaction will rotate plane polarized light.

Enantiomers

Enantiomers are having same chemical formula but they are non- superimposable mirror images of each other. Enantiomers should have one chiral center and these are having same physical and chemical properties. 

Two types of enantiomers are there i.e. erythro enantiomers and threo enantiomers. The enantiomers having similar groups on the same side are known as erythro enantiomers and the enantiomers having similar groups on the different side are known as threo enantiomers. 

Example

Enantiomers have different configurations.

Example of erythro and threo enantiomers:

Observation

In the presence of  ozonolysis reaction will take place. In this reaction oxidative cleavage of double bond will take place and we will get the product mixture as shown below:

In this the product of reaction has one chiral center having four different groups and this is enantiomer therefore, it will rotate plane polarized light.