1. Provide a multistep synthesis for ONE of the two problems below. You get to choose. If you do work on each, make it VERY CLEAR WHICH ONE YOU WANT GRADED. Note that each carbon in your final product must originate from the given starting material. You have an infinite supply of that starting material. You also have an infinite supply of anything you make from it. You can use any other reagents you want, and you do not have to make them yourself, as long as they do not become part of your final product structure. For example, if you use CH3CH2O (ethoxide) as a strong base for an E2, you do not have to make it. If you use it as a nucleophile for SN2 and it becomes part of your product, then you do have to make it. Addressing some common questions from students: You are not asked to provide any arrow-pushing mechanisms. You are not required to show a retrosynthetic analysis. You can receive full credit for, at minimum, having a correct sequence of reactions even without showing any products along the way. You can receive partial credit for your synthetic intermediates, which are just the products made along the way, whether as part of a retrosynthesis or forward synthesis. 6 points only C source ° | H H only C source (rac)

1. Provide a multistep synthesis for ONE of the two problems below. You get to choose. If you do work on each, make it VERY CLEAR WHICH ONE YOU WANT GRADED. Note that each carbon in your final product must originate from the given starting material. You have an infinite supply of that starting material. You also have an infinite supply of anything you make from it. You can use any other reagents you want, and you do not have to make them yourself, as long as they do not become part of your final product structure. For example, if you use CH3CH2O (ethoxide) as a strong base for an E2, you do not have to make it. If you use it as a nucleophile for SN2 and it becomes part of your product, then you do have to make it. Addressing some common questions from students: You are not asked to provide any arrow-pushing mechanisms. You are not required to show a retrosynthetic analysis. You can receive full credit for, at minimum, having a correct sequence of reactions even without showing any products along the way. You can receive partial credit for your synthetic intermediates, which are just the products made along the way, whether as part of a retrosynthesis or forward synthesis. 6 points only C source ° | H H only C source (rac)

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter16: Synthesis Workshop 1

Section: Chapter Questions

Problem 25E

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