Organic Chemistry
Organic Chemistry
2nd Edition
ISBN: 9781118452288
Author: David R. Klein
Publisher: WILEY
Question
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Chapter 5, Problem 32PP
Interpretation Introduction

Interpretation: The configuration and chirality should be identified for the given molecule by using its structure.

Concept Introduction:

Chiral carbon: Chiral atom is the one which is bonded to four different molecules or groups.

Configuration of a molecule: The configurations of a molecule arise due to the spatial arrangement of atoms. The configuration can be assigned by following CIP rules as follows.

Rules

Find the chiral carbon atom in a molecule.

Assign numbering to the groups bonded to the chiral carbon based on the molecular weight and electronegativity.

If the sequence of the numbering follows clockwise direction the chiral atom is assigned as R configuration.

If the sequence of the numbering follows anticlockwise direction the chiral atom is assigned as S configuration

The R and S configuration of a molecule can be interchanged when a least prior group present in above plane.

To find: The chiral atoms present of the given molecule.

Expert Solution & Answer
Check Mark

Answer to Problem 32PP

The R and S nomenclature for the given molecule are shown below.

Organic Chemistry, Chapter 5, Problem 32PP , additional homework tip  1      Organic Chemistry, Chapter 5, Problem 32PP , additional homework tip  2

Explanation of Solution

  • Draw the structure of the given molecule and find the chiral centers.

Organic Chemistry, Chapter 5, Problem 32PP , additional homework tip  3

Chiral centers of the molecule are indicated by using *

The chiral center in the given molecule is marked using*. The * Carbons are chiral since all the carbons are sp3 hybridized and it is bonded to four different groups namely OH,CH3,CH2andH. The chirality structure for the given molecule is drawn by which different groups linked to the same central carbon atoms. (For example one –OH group were attached in axial position carbon atoms).

The presence of an asymmetric carbon center is one of several structural features that induce chirality in organic molecules.

  • Assign absolute configuration R-S for the given molecules using CIP rules.

Organic Chemistry, Chapter 5, Problem 32PP , additional homework tip  4 Organic Chemistry, Chapter 5, Problem 32PP , additional homework tip  5

Chiral carbons are labeled as shown above molecules. Further the right and left hand nomenclature is used to name the enantiomers of chiral compounds. The stereocenter are indicated as R or S.

From the priority is assigned of the above molecules, according to the substitution of elements with higher atomic number, or other attached groups.

Conclusion
For the given organic molecule the chiral centers and absolute configuration is identified by analyzing by R-S sequence rules.

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