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 17PP
Interpretation Introduction

Interpretation:

The substructure that would have an R designation is to be drawn from the given structure.

Concept Introduction:

▸ The molecules which are non-superimposable or not identical with their mirror images are known as chiral molecules.

▸ A pair of two mirror images which are non-identical is known as enantiomers which are optically active.

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

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

▸ 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.

▸ Priority is given to all the four group attached to the chirality center.

▸ Priority is assigned on the basis of the atomic number of the atom. Higher the atomic number, higher will be its priority.

▸ If priority cannot be assigned according to atomic mass, then, it is assigned according to first point of difference.

▸ After assigning priority to the four groups, rotate the molecule such that fourth priority group is away from the observer.

▸ Now, move from a to b to c; if the direction is clockwise, then the chiral center designated as (R) and if the direction is anticlockwise, then the chiral center designated as (S).

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(b) (c) Draw the more stable chair conformation of each of the following compounds in which an sp³-hybridized heteroatom is part of the ring. ZI
h 1.73 Consider the three compounds shown below and then answer the questions that follow: H H H H-C-C-C-C H H H H Compound A -CN-H H. H H-C-N. H H-C-C-H H H H Compound B Η Η Η H-C-C-C=N: H H H Compound C ( 2

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