Organic Chemistry: Structure and Function
Organic Chemistry: Structure and Function
8th Edition
ISBN: 9781319079451
Author: K. Peter C. Vollhardt, Neil E. Schore
Publisher: W. H. Freeman
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Chapter 5, Problem 35P
Interpretation Introduction

Interpretation: Either of one of the enantiomeric forms of below chiral molecules should be drawn and stereochemistry of carbon should be labeled.

  Organic Chemistry: Structure and Function, Chapter 5, Problem 35P

Concept introduction: In order to assign absolute configuration of R and S, Cahn − Ingold − Prelog rules are used and the first step is to assign the priority order on the basis of atomic number. The one with highest atomic number gest highest priority and is designated as a and so on.

The Fischer projection is written along with the priorities assigned and groups are interchanged between adjacent places so as to obtain lowest priority group at the bottom or lowest priority.

If the groups arranged are read from highest towards least in clockwise fashion then R is assigned to the stereocenter.If the rotation is anticlockwise then S is assigned at the configuration.

The enantiomers are identical chemical compounds that have a mirror-image relationship to each other while diastereomers do not hold mirror image relationships. The former are chiral and optically active while the latter can be chiral or achiral.

Any organic compound must have no plane of symmetry in order to be optically active. The compounds with any plane of symmetry are achiral and optically inactive.

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