有機化學第14ç« ï&f

有機化學第14ç« ï&f

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Unformatted text preview: 2009/3/31 1 14. Conjugated Compounds and Ultraviolet Spectroscopy 共軛雙鍵與紫外光譜 Based on McMurry’s Organic Chemistry , 7 th edition Conjugated and Nonconjugated Dienes Compounds can have more than one double or triple bond If they are separated by only one single bond they are conjugated and their orbitals interact 2 The conjugated diene has properties that are very different from those of the nonconjugated diene 2009/3/31 2 Why this Chapter? Conjugated compounds are common in nature Extended conjugation leads to absorption Extended conjugation leads to absorption of visible light, producing color Conjugated hydrocarbon with many double bonds are polyenes 3 Examine properties of conjugated molecules and reasons for the properties Polyenes Compounds with many alternating single and double bonds Extended conjugation leads to absorption of visible light, producing color (lycopene 蕃茄紅素 is responsible for red color in tomatoes) Extended conjugation in ketones (enones) found in hormones such as progesterone 黃體酮 2009/3/31 3 OUTLINE ¡ Stability of Conjugated Dienes: Molecular Orbital Theory Molecular Orbital Theory ¡ Electrophilic Additions to Conjugated Dienes: Allylic Carbocations ¡ Kinetic vs. Thermodynamic Control of Reactions ¡ The Diels-Alder Cycloaddition Reaction ¡ Characteristics of the Diels-Alder Reaction ¡ Diene Polymers: Natural and Synthetic Rubbers 5 OUTLINE ¡ Structure Determination in Conjugated Systems: UV Spectroscopy UV Spectroscopy ¡ Interpreting UV Spectra: The Effect of Conjugation ¡ Conjugation, Color and the Chemistry of Vision 6 2009/3/31 4 14.1 Stability of Conjugated Dienes: Molecular Orbital Theory Typical Method to Prepare Diene by elimination in allylic halid e 7 Industrial Processes of Isoprene 8 Chloroprene 2-chloro-1,3-butadiene 2009/3/31 5 The single bond between the conjugated double bonds is shorter and stronger than sp 3 各種烯類加氫處理所放之熱 2009/3/31 6 Measuring Stability Conjugated dienes are more stable than...
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有機化學第14ç« ï&f

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