Chapter14 - Conjugated and Nonconjugated Dienes 14....

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1 14. Conjugated Dienes and Ultraviolet Spectroscopy Based on McMurry’s Organic Chemistry , 6 th edition 2 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 ± The conjugated diene 1,3-butadiene has properties that are very different from those of the nonconjugated diene , 1,5-pentadiene 3 Polyenes ± Compounds with many alternating single and double bonds ± Extended conjugation leads to absorption of visible light, producing color ± Conjugated hydrocarbon with many double bonds are polyenes (lycopene is responsible for red color in tomatoes) ± Extended conjugation in ketones (enones) found in hormones such as progesterone 4 14.1 Preparation and Stability of Conjugated Dienes ± Typically by elimination in allylic halide ± Specific industrial processes for large scale production of commodities by catalytic dehydrogenation and dehydration
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2 5 Measuring Stability ± Conjugated dienes are more stable than nonconjugated based on heats of hydrogenation ± Hydrogenating 1,3-butadiene takes up 16 kJ/mol more heat than 1,4-pentadiene 6 Molecular Orbital Description of Bonding ± Isolated p -orbitals combine to give bonding and anti- bonding orbitals 7 14.2 Molecular Orbital Description of
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Chapter14 - Conjugated and Nonconjugated Dienes 14....

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