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 5.1, Problem 5.3E

(a)

Interpretation Introduction

Interpretation:The natural products indicated should be identified as either chiral or achiral.

  Organic Chemistry: Structure and Function, Chapter 5.1, Problem 5.3E , additional homework tip  1

Concept introduction:

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.

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

Presence of any symmetry element makes molecule achiral and optically inactive.

(b)

Interpretation Introduction

Interpretation: The three molecules that represent enantiomers of 2-chlorobutane and two that are its mirror images should be identified.

  Organic Chemistry: Structure and Function, Chapter 5.1, Problem 5.3E , additional homework tip  2

Concept introduction: 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.

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