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 2PP
Interpretation Introduction

Interpretation:

The stereochemistry of 2bromopropane is to be discussed.

Concept introduction:

The compounds which are non-superimposable or not identical with their mirror images are known as chiral objects. The pair of two mirror images which are non-identical is known as enantiomers. Enantiomers have same physical and chemical properties in an achiral environment and they rotate the direction of polarized light to equal, but opposite angles.

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

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Drawn below are the structures of (+)-menthol and (-)-menthol. These are stereoisomers of one another. They have identical physical properties are indiscernible by most laboratory techniques (e.g. melting point, boiling point, IR spectroscopy), except they interact with polarized light differently (hence the +/- designation). Curiously, they can be perceived differently by humans by our sense of smell. (a) Make a model of the structures or draw them both and describe how they are related geometrically. (b) Why is it that these nearly physically identical compounds can be discerned by our sense of smell? OH HO (+)-menthol (-)-menthol
For each pair of compounds, predict which one has the higher molecular dipole moment, and explain your reasoning.(a)  cis-1,2-dichlorocyclobutane or trans-1,3-dichlorocyclobutane
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