Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second)
Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second)
2nd Edition
ISBN: 9780393655551
Author: KARTY, Joel
Publisher: W. W. Norton & Company
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Chapter 14, Problem 14.23P
Interpretation Introduction

Interpretation:

Assuming the given compound is planar, it is to be determined and explained whether it is aromatic, antiaromatic, or nonaromatic.

Concept introduction:

Electrons can be resonance delocalized over a set of atoms that contribute conjugated p-orbitals to a single π system of molecular orbitals. For an acyclic conjugated system, the π electrons are the ones that can be shifted via resonance from one end to the other. Counting of the π systems and number of electrons is useful when a compound contains a triple bond. According to the MO theory, the two pi bonds are perpendicular to each other in a triple bond. Therefore, only one of those pi bonds can be conjugated with the neighboring π system.

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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.

Chapter 14 Solutions

Organic Chemistry: Principles And Mechanisms: Study Guide/solutions Manual (second)

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