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 26PP
Interpretation Introduction

Interpretation:

In compounds A and B, the (R,S) designation for each chirality center is to be given and for compound C, which is a diastereomer of A and B, the Fischer projection formula is to be written and stereoisomeric property are to be discussed.

Concept Introduction:

The molecules which are non-superimposable or not identical with its mirror image are known as chiral molecules.

The pair of two mirror images which are non-identical are known as enantiomers and these are optically active.

The enantiomers, in which the path traced from the highest atomic number to the lowest atomic number is in an anticlockwise direction, are designated as S.

The enantiomers, in which the path traced from the highest atomic number to the lowest atomic number is in the clockwise direction, are designated as R.

The objects or molecules which are superimposable with its mirror images are achiral objects or molecules and these objects have a centre of symmetry or plane of symmetry.

The achiral compounds in which the plane of symmetry is present internally and consists of chiral centres are known as meso compounds, but they are optically inactive.

The stereoformula which is depicted in two dimensions, in which stereochemical information is not destroyed, is determined by the Fisher Projection formula.

The stereoisomers which are non-superimposable on each other and not mirror images of each other are known as diastereomers.

Chiral molecules are capable of rotating plane polarized light

The molecules which are superimposable or identical with their mirror images are known as achiral molecules, and achiral molecules are not capable of rotating the plane-polarised light.

Plane of symmetry is the plane that bisects the molecule in two equal halves, such that they are mirror images of each other.

Compounds having plane of symmetry are usually achiral as they do not have different atoms around the central carbon atom.

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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
Please answer D, E, F
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.

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