浙江大学马成有机化学乙课件 Chapter 7 Conjugation in Alkadienes and Allylic Systems.pdfVIP

Chapter 7: Conjugation in Alkadienes and Allylic Systems 2009/9/13 1 Summary A adjacent πsystem in the form of a double (or triple) bond can alter the characteristic chemistry of the functional group, due to the effects of resonance within a conjugated system This πsystem does not have to be all C as in a C=C or C≡C but can also contain heteroatoms, e.g. C=O or C≡N 1. Functional groups (independent units, conjugation units) 2. Allylic System 3. Dienes 4. Conjugation addition 5. Diels-Alder Reaction (M.O.) 2009/9/13 2 7.1 Conjugation 1. Some Dienes and Polyenes 2009/9/13 3 2. Conjugation In organic chemistry, Conjugation is used to describe: π −π systems p - π systems σ- π systems Character: Lowered Molecule Energy 1)The action not decrease with the distance in the conjugation system 2)Charge changes one by one (electronegativety, electronic charge) Comared to inductive effect ! The fundamental Orbital involved in the bonding within the system 1) A continuous array of p orbitals that can align to produce a bonding overlap along the whole system. (parallel and co-plane) 2) In σ- π systems ,with σ orbitals , Pseudo-conjugation or Super- conjugation The Effect of three Conjugation: π –π p - π σ- π 2009/9/13 4 π –π O C C C C C C C N C C C H C C C C C C 2009/9/13