Organic Chemistry: Principles And Mechanisms
Organic Chemistry: Principles And Mechanisms
2nd Edition
ISBN: 9780393663549
Author: KARTY, Joel
Publisher: W. W. Norton and Company
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Chapter C, Problem C.13P
Interpretation Introduction

Interpretation:

The configuration of the double bond as E or Z, in the given molecule, is to be determined.

Concept introduction:

When assigning priorities to substituents, the atom having the greater atomic number has higher priority. In case of comparison between isotopes, the one having the greater atomic mass gets higher priority. If the substituents are attached by the same atom, then the set of atoms one bond away from the point of attachment are compared. In each set, highest priority atoms are compared. If the sets of atoms one bond away from the point of attachment are identical, then the sets of atoms one additional bond away from the point of attachment are compared. If the higher priority groups, attached to the double bonded carbon atoms, are on the same side of the double bond, the alkene is assigned Z configuration. If the higher priority groups, attached to the double bonded carbon atoms, are on the opposite side of the double bond, the alkene is assigned E configuration.

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Please answer the question and provide a detailed drawing of the structure. If there will not be a new C – C bond, then the box under the drawing area will be checked.  Will the following reaction make a molecule with a new C – C bond as its major product:  Draw the major organic product or products, if the reaction will work. Be sure you use wedge and dash bonds if necessary, for example to distinguish between major products with different stereochemistry.
Please do not use AI.  AI cannot "see" the molecules properly, and it therefore gives the wrong answer while giving incorrect descriptions of the visual images we're looking at.  All of these compounds would be produced (I think).  In my book, I don't see any rules about yield in this case, like explaining that one product would be present in less yield for this reason or that reason.  Please explain why some of these produce less yield than others.
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