Organic Chemistry
Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 7, Problem 7.31P

Using your reaction roadmap as a guide, show how to convert acetylene and bromoethane into 1-butene. All of the carbon atoms of the target molecule must be derived from the given starting materials. Show all intermediate molecules synthesized along the way.

Chapter 7, Problem 7.31P, Using your reaction roadmap as a guide, show how to convert acetylene and bromoethane into 1-butene.

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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.
Please answer the question and provide detailed explanations.

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How to Design a Total Synthesis; Author: Chemistry Unleashed;https://www.youtube.com/watch?v=9jRfAJJO7mM;License: Standard YouTube License, CC-BY