Chapter 15 - Wade(1)

Chapter 15 - Wade(1) - Introduction to General and Organic...

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Chapter 15 Conjugated Systems Dr. David P. Brown Department of Chemistry Introduction to General and Organic Chemistry III
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Chaper 15 2 Introduction Conjugated double bonds are separated by one single bond. Example : 1,3- pentadiene . Isolated double bonds are separated by two or more single bonds. 1,4-pentadiene . Cumulated double bonds are on adjacent carbons. Example : 1,2-pentadiene .
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Chaper 15 3 Resonance Energy Heat of hydrogenation for trans -1,3- pentadiene is less than expected . 2200 H for 1-pentene is 30.0 kcal/mol and for trans -2-pentene is 27.4 kcal/mol, so expect 57.4 kcal for trans -1,3-pentadiene. Actual H is 53.7 kcal , so the conjugated diene is more stable. Difference, (57.4 – 53.7) 3.7 kcal/mol , is the resonance energy . =>
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Chaper 15 4 Relative Stabilities twice 1-pentene more substituted
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5 Structure of 1,3-Butadiene Most stable conformation is planar.
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Chapter 15 - Wade(1) - Introduction to General and Organic...

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