ORGANIC CHEMISTRY (LL) W/WILEYPLUS NEXT
ORGANIC CHEMISTRY (LL) W/WILEYPLUS NEXT
12th Edition
ISBN: 9781119664635
Author: Solomons
Publisher: WILEY
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Chapter 5, Problem 42P
Interpretation Introduction

Interpretation:

The given pairs of compounds are to be identified as diastereomers, enantiomers, constitutional isomers and not isomeric.

Concept Introduction:

Isomers are molecules which have same number of atoms but different arrangements of the atoms in space.

Stereoisomers have the same molecular formula, but the arrangement of atoms in the three-dimensional orientation is different.

Enantiomers are stereoisomers whose molecules have a chiral center and are mirror images of each other.

Diastereomers are stereoisomers that are not mirror images of each other. They are non-superimposable.

Molecules whose atoms are connected differently are called constitutional isomers.

Meso are those compounds whose molecules are superimposable on their image mirrors in spite of the presence of asymmetric carbon atom.

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.

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

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(a) assign R or S configuration to each chiral center, (b) Which compound are enantiomers? (c) Which compounds are diastereomers?
Coibacin B (shown below) is a natural product that exhibits potent anti-inflammatory activity and potential activity in the treatment of leishmaniasis, a disease caused by certain parasites (Org. Lett. 2012, 14, 3878-3881): (a) Assign the configuration (R or S) of each chirality center (labeled A to C) in coibacin B. (b) Identify the number of possible stereoisomers for this compound, assuming that the geometry of the alkenes are fixed. Choices are given below and write the CAPITAL LETTER of your choice. A. 2 В. 4 С. 8 D. 16 ANSWERS: (a) A. В. C. (b)
4. (a) Draw all possible isomers of C4H3CI2. (b) Indicate which pairs of compounds are enantiomers of one another. (c) Indicate which pairs of compounds are diastereomers of one another. (d) Indicate which compounds would have optical rotations of 0°. (e) Assign R and S configurations to all chirality centers of the compounds in part (a).

Chapter 5 Solutions

ORGANIC CHEMISTRY (LL) W/WILEYPLUS NEXT

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