Lecture #1

Lecture #1 - Chapter 13: Conjugated Unsaturated Systems!...

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Chapter 13: Conjugated Unsaturated Systems Reactivity in saturated vs. unsaturated compounds C=C + A-B ! - bond " - bond bonds lost C-C A B ! - bonds bonds gained C C : + H-X C C + H + X - carbocation
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Focus on molecules that have a p-orbital on the atom adjacent to the double bond. CH H 2 C CH 3 No p-orbital on adjacent carbon CH H 2 C CH 2 or CH H 2 C CH 2 C + sp 2 hybridization sp 2 p z a planar geometry C H H H . electron in p orbital
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Conjugated Unsaturated Systems have a p-orbital on the atom adjacent to a double bond and give rise to extended, delocalized π bonds. C=C-C conjugated unsaturated system Conjugation means a ! -system extended by p-orbitals on adjacent carbons. C C C A ! -system of three overlapping p-orbitals is called allylic . an allylic cation, radical or anion H 2 C H C C H CH 2 Compounds with adjacent multiple bonds are also conjugated unsaturated systems
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Conjugated molecules have interesting properties and reactivity 1. More stable than non-conjugated analogues 2. Often are highly colored (absorb visible light) 3. Undergo unusual reactions
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Allylic Substitution and the Allylic Radical Propene reacts with Br 2 and Cl 2 by the usual electrophilic addition reaction at room temperature in the absence of ultraviolet radiation. CH 3 CH=CH 2 + X 2 room temp no h ! CH 3 CH X CH 2 X Electrophilic Addition Allylic Substitution At high temperatures, and under conditions where [X 2 ] is low, allylic substitution occurs:
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Lecture #1 - Chapter 13: Conjugated Unsaturated Systems!...

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