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 14.5YT
Interpretation Introduction

Interpretation:

The carbon-carbon bond lengths in ethane and ethene are to be compared to those in cyclobutadiene.

Concept introduction:

The normal bond length of carbon-carbon single bond is 154 pm while that for carbon-carbon double bond is 132 pm. In cyclic conjugated compounds, due to resonance stabilization, carbon-carbon bond length of single bond significantly shows double-bond character and is substantially shorter than a normal carbon-carbon single bond and longer than a normal double bond.

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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.

Chapter 14 Solutions

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

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