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Chapter 5: Q.22 (page 195)

If the two stereogenic centers of a compound are R,S in configuration, what are the R,S assignments for its enantiomer and two diastereomers?

Short Answer

Expert verified

R, R for enantiomers.

R, R and S, S for diastereomers.

Step by step solution

01

Enantiomers  

The enantiomers contain chiral centers (with four different groups), and they are identified by the inverted stereochemistry.

For example, the R isomer, and S isomer are enantiomers.

02

Diastereomers

The diastereomers also contain chiral centers or stereogenic centers, and they are identified by the difference in stereochemistry at only one center.

For example, the R, S isomer and R, R isomer are diastereomers.

03

Explanation

  1. The R, S assigned molecule has its enantiomer with S, R stereochemistry. The stereochemistry is inverted in this case due to non-superimposable mirror images.
  2. The R, S assigned molecule has its diastereomer with S, S stereochemistry. The stereochemistry of one chiral atom remains the same in this case due to not having any mirror image relationship.

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Most popular questions from this chapter

a. Locate the stereogenic centres in the ball-and-stick model of lisinopril, a drug used to treat high blood pressure.

b. Label each stereogenic centre as R or S.

Draw all the possible stereoisomers for each compound and label pairs of enantiomers and diastereomers.

a.

b.

Locate the stereogenic centers in each molecule. Compounds may have one or more stereogenic centers.

a.

b.

c.

d.

e.

f.

Label each stereogenic center as R or S.

a.

b.

c.

d.

e.

f.

g.

h.

Draw in a plane of symmetry for each molecule.

a.

b.

c.

d.
See all solutions

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