Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 5, Problem 15PP
Interpretation Introduction

Interpretation:

The percent enantiomeric excess and the enantiomer that is in excess are to be determined.

Concept introduction:

The molecules that are non-superimposable or not identical with their mirror images are known as chiral molecules. Chiral molecules have the capability to rotate plane-polarized light.

A pair of mirror images that are non-identical is known as a pair of enantiomers.

The enantiomers in which the path traced from the highest to the lowest atomic number is in the anticlockwise direction are designated as S provided that among the four groups attached to the chiral carbon, the least priority group is in horizontal position in Fischer projection.

The enantiomers in which the path traced from the highest to the lowest atomic number is in the clockwise direction are designated as R provided that among the four groups attached to the chiral carbon, the least priority group is in horizontal position in Fischer projection.

In a solution, as light is passed through a sample, the orientation of the monochromatic plane-polarized light changes. This change is known as specific rotation ([α]).

The difference between the values of mole fractions of two enantiomers is called the enantiomeric excess.

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If molecules A and B are isomers of each other, then what kinds of isomers could they be (i.e., enantiomers, diastereomers, or constitutional isomers) under each of the following conditions?(a) Both molecules have the same IHD.(b) Molecule A has a ring but molecule B does not.(c) Molecules A and B contain different functional groups.(d) Molecules A and B share exactly the same functional groups.(e) Molecule A has a plane of symmetry but molecule B does not.
• PRACTICE PROBLEM 5.22 Write three-dimensional formulas for all of the stereoisomers of each of the following compounds. Label pairs of enantiomers and label meso compounds. enslg a nsudomotaib esvierd ofni oluelom oreovb dase to ope.n 1oim s ier 1erto (a) ibaong (b) A boemo OH (c) CI ОН CI F F OH win vle (f) HO,C. (d) (e) OH CI CO,H Br im slm (b) OH Tartaric acid
5:51 Draw examples of the following: (a) A meso compound with the formula C8H18 (b) A meso compound with the formula C9H20 (c) A compound with two chirality centers, one R and the other S

Chapter 5 Solutions

Organic Chemistry

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