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Chapter 5: Q39E (page 148)

What is the stereochemical configuration of the enantiomer of (2S,4R)-2,4-octanediol? (A diol is a compound with two-OH groups.)

Short Answer

Expert verified

Stereochemical configurationcharacterises a particular stereoisomer by the atoms or the groups of atoms.

Stereochemical configurations are of two types:

  • Absolute configuration- R, S system
  • Relative configuration D-L system

Step by step solution

01

Step 1:Stereochemical configuration

Stereochemical configurationcharacterises a particular stereoisomer by the atoms or the groups of atoms.

Stereochemical configurations are of two types:

  • Absolute configuration- R, S system
  • Relative configuration D-L system
02

Step 2:Stereochemical configuration of (2S,4R)-2,4-octanediol

The enantiomer of (2S,4R)-2,4-octanediol will be opposite in the configuration;that is, the 2S,4R configuration at the chiral centre will be changed to 2R,4S.

The 2S,4R configuration and 2R,4S configuration of 2,4 -octane diol are non-suoerimposible mirror images of each other due to a lack of symmetry in the molecule:

  • Lack of centre of symmetry
  • Lack of plane of symmetry

The Stereochemical configuration of (2S,4R)-2,4-octane diol is shown as follows:

Stereochemical configuration of (2S,4R)-2,4-octane diol

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Most popular questions from this chapter

Orient each of the following drawings so that the lowest-ranked group is toward the rear, and then assign R or S configuration:

a.

b.

c.

Question:Identify the chirality centers in the following molecules (green5Cl, yellow-green5F):

Draw both cis- and trans-1,3-dimethyl cyclohexane in their more stable chair conformations.

(a) How many stereoisomers are there of cis-1,3-dimethyl cyclohexane, and how many of trans-1,3-dimethyl cyclohexane?

(b) Are any of the structures chiral?

(c) What are the stereochemical relationships among the various stereoisomers of 1,3-dimethyl cyclohexane?

Ribose, an essential part of ribonucleic acid (RNA), has the following structure:

(a) How many chirality centers does ribose have? Identify them.

(b) How many stereoisomers of ribose are there?

(c) Draw the structure of the enantiomer of ribose.

  1. Draw the structure of a diastereomer of ribose.

Assign R or S configurations to the chirality centers in the following molecules (blue = N)
See all solutions

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