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 5.7, Problem 5.26TIY
Interpretation Introduction

Interpretation: The structures of the products of monobromination of (S)-2-bromopentane at each carbon atom should be written as well as name of the products, the optically active forms along with their chiral or achiral nature and whether formation will occur in equal or unequal amounts should be identified.

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 now are arranged are read from highest towards least in clockwise fashion the R is assigned to the stereocenter, if the rotation is anticlockwise the S is assigned at the configuration.

Four kinds of symmetry elements that may be present are tabulated as follows:

  S.NoSymmetry elementNotation1.Axis of symmetryCn2.Plane of symmetryσ3. Alternating axis of  symmetrySn4.Center of symmetryi

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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