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 20PP
Interpretation Introduction

Interpretation:

The optically active compounds among the given compounds are to be identified.

Concept introduction:

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

A pair of two mirror images that are non-identical is known as a pair of enantiomers, and these are optically active.

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. .

The objects or molecules which are superimposable with their mirror images are achiral objects or molecules. 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.

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(a) All Isomers have the same molecular formulae. Explain this further. Hint what does it mean to have the same molecular formulae? (b) What is Constitutional (structural) isomerism? Hint, isomers are different, so what is different between a pair of constitutional isomers (see the chart on the last page for examples). (c) What is Conformational isomerism?
5.76 2,3-Dibromoprop-1-ene (C3H4Br₂) has four H atoms. Suppose that any of these H atoms can be replaced by a Cl atom to yield a molecule with the formula C3H3Br₂Cl. (a) Identify two H atoms where this substitution would yield constitutional isomers of C3H3Br₂Cl; (b) enantiomers of C3H3Br₂Cl; (c) diastereomers of C3H3Br₂Cl. co 11 HHH Juods H Brugtrio 2 bas A 2,3-Dil so ontemme A chon Br 2,3-Dibromoprop-1-ene
2.35 Consider 1-bromo-2-methylpropane and draw the following.(a) The staggered conformation(s) of lowest energy(b) The staggered conformation(s) of highest energy

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