Organic Chemistry
Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 6, Problem 6.32AP
Interpretation Introduction

Interpretation:

The structure of the chiral alkane which has the lowest molecular mass and do not contain a ring is to be drawn.

Concept introduction:

A carbon atom that has four nonequivalent atoms or groups attached to it is known as the chiral carbon atom. Chiral carbon centers are also called asymmetric or stereogenic centers. A carbon atom that does not have four nonequivalent atoms or groups attached to it is known as an achiral carbon atom.

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For the cyclohexane structures shown below, draw both chair structures for each and identify which is lower in energy (briefly explain why).
I'm confused as to why the chiral centers are the was they are. I understand that the horizontal lines are wedged and vertical are dashed. Wouldn't the first priority be the carboxylic acid, then alcohol, the carbon, and then the hydrogen? The book is saying that one method is to keep two of the straight lines and pick one group to be dashed and one to be wedged. Then switch the last priority group (H) with whatever group you chose to be on the dash. Whatever configuration you get, make it the opposite since you switched groups. And when I use this method I end up getting S when the top one should be R.
Consider the structure of the molecule below The absolute configuration (R/S) of the chiral carbon with chlorine is The enantiomer of this structure is (draw it to the right): Draw a constitutional isomer of the molecule (draw it to the right):
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