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Yale University

Proving the Configuration of Glucose and Synthesizing Cyclobutadiene - Lecture 37

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Overview

Explore the structure, constitution, and configuration of glucose in this 55-minute lecture from Yale University's Freshman Organic Chemistry II course. Delve into the historical development of glucose analysis, from van't Hoff's early work to the Kiliani-Fischer synthesis. Examine Fischer's groundbreaking methods, including osazones and projections, which led to the proof of glucose's configuration. Learn about modern spectroscopic tools for analyzing glucose's structure and isomeric interconversions. Discover the synthesis of cyclobutadiene precursors using designer clamshell molecules, and investigate the antiaromaticity of cyclobutadiene. Gain insights into the evolution of organic chemistry techniques and their application in understanding complex molecular structures.

Syllabus

- Chapter 1. Glucose Structure by IR, NMR, and X-Ray
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- Chapter 2. Glucose Constitution from van't Hoff to the Kiliani-Fischer Synthesis
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- Chapter 3. Fischer's Osazones, Fischer's Projection, and Fischer's Evidence
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- Chapter 4. Fischer's Proof of the Configuration of Glucose
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- Chapter 5. Synthesizing a Cyclobutadiene Precursor in a Designer Clamshell
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- Chapter 6. The Antiaromaticity of Cyclobutadiene
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