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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

Question:Which of the following molecules are chiral? Identify the chirality center(s) in each.

(a)

Coniine

(poison hemlock)

(b)

Menthol

(flavoring agent)

(c)

Dextromethorphan

(cough suppressant)

Which of the following objects are chiral?

(a) A basketball

(b) A fork

(c) A wine glass

(d) A golf club

(e) A spiral staircase

(f) A snowflake

(b)

Xylose is a common sugar found in many types of wood, including maple and cherry. Because it is much less prone to cause tooth decay than sucrose, xylose has been used in candy and chewing gum. Assign R or S configurations to the chirality centers in xylose.

The dehydration of citrate to yield cis-aconitate, a step in the citric acid cycle, involves the pro-R “arm” of citrate rather than the pro-S arm. Which of the following two products is formed?

Which of the following pairs of structures represent the same enantiomer, and which represent different enantiomers?
See all solutions

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