Chapter 4, Problem 39P

Interpretation Introduction

Interpretation:

The number of stereoisomers in muscarine is to be determined. The number of stereoisomers in which one of the substituents on the ring is trans to the other two is to be determined. The structural formula of muscarine having the configuration $\text{2S,3R,5S}$ is to be written.

Concept introduction:

For a particular stereoisomer, the maximum number of stereoisomers ${\text{2}}^{\text{n}}$, where n is equal to the number of chirality centers.

When determining the configuration, the molecule is oriented such that the lowest ranked atom points away from the observer.

The order of decreasing priority of the three other atoms or groups is determined. If it traces a clockwise path, the configuration is R, and if it traces a counterclockwise path, the configuration is S.

In cycloalkanes, the groups that lie on the opposite side of the ring are trans to each other.