9.8: Stereochemistry of Reactions - Hydration of Chiral Alkenes
- Page ID
- 110176
Learning Objective
- discern the stereochemical differences between the EAR of chiral and achiral alkenes
Stereochemistry - the Subtle Details
In the previous section, the addition of water to the achiral alkene produced a racemic mixture of two enantiomeric alcohols. They are produced in equal amounts so the mixture is optically inactive. What would occur if we carried out a similar reaction on a chiral alkene? Consider (S)-3-methyl-1-pentene reacting with water (acid catalyzed). Proton addition produces a carbocation intermediate that is chiral (* denotes stereogenic centre). That intermediate does not have a plane of symmetry and therefore attack by water is not equal from the top and bottom. This ultimately produces R and S products in a non 50:50 ratio as shown in the mechanism below.
Exercise
1. Predict the products of the following reaction showing stereochemistry.
- Answer
-
1. The products are diastereomers of one another.
Contributors and Attributions
Dr. Dietmar Kennepohl FCIC (Professor of Chemistry, Athabasca University)
Prof. Steven Farmer (Sonoma State University)