Chapter 15 Conjugated Systems

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1 Chapter 15 Cnjugated Systems What makes a cnjugated system? When yu have alternating duble bnds, the electrns f the pi system can flw ver a lnger length. This is cnjugatin. Stabilities f Dienes Cnjugated alternating duble bnds Islated the duble bnds are separated by at least ne sp 3 carbn Cumulated this is an allene C Stability cnjugated>islated>cumulated Resnance energy the additinal stability gained frm resnance by cnjugated systems as ppsed t islated duble bnds Dn t wrry abut mlecular rbitals Additin f X t cnjugated dienes When yu add the prtn t a cnjugated diene, yu have the chice f fur places t put it. If yu put it at ne f the utside spts, yu will get an allylic carbcatin Br Ex. Outside placement f the prtn Inside placement f the prtn

2 Because f this resnance-stabilizatin, the majr prduct always has the prtn added t an utside psitin Once yu ve narrwed it dwn t the tw utside psitins, then yu need t lk at bth resnance structures fr each f the pssible prtn placements. 2 allylic 1 allylic 2 allylic 3 allylic Find the prtn placement that gives yu the mst stable carbcatin and crss ut the less stable ne 2 allylic 1 allylic

3 2 allylic 3 allylic The mre stable intermediate gives yu the kinetic prduct. lw temp Br 3 allylic The mre stable prduct is the thermdynamic prduct. high temp Br tri-substituted duble bnd 1,2- vs. 1,4- additin This is just a way f describing what happened when yu went thrugh all f the steps abve. Call the carbn where yu added the prtn 1. If the halgen is at carbn #2, then it was 1,2-additin If the halgen is at carbn #4, then it was 1,4-additin D nt tell yurself that the kinetic prduct is always 1,2-additin and the thermdynamic prduct is always 1,4- (r vice-versa). There is n crrelatin! SN1 with allylic intermediates Once the carbcatin frms, yu can get an allyl shift

4 Br C3O C C O O SN2 with allylic leaving grups Even SN2 is helped ut by allylic and benzyllic psitins. Azide in is N3 - Prpellant used in airbags Allylic Radicals Drawing resnance with radicals is a little mre invlved C C Use NBS t brminates at allylic psitins If yu want t brminates an alkene, yu will get sme allylic brminatin, but yu will als get additin acrss the duble bnd. T prevent this, add NBS (n-brmsuccinimide) r NCS fr chlrine Diels-Alder The Mst Magical Reactin f the Curse! An electrn-rich cnjugated diene reacts with an electrn-pr alkene r alkyne t frm a six-membered ring If the dienphile is an alkene, the prduct will have a template that lks like the mlecule n the right abve. If the dienphile is an alkyne, the prduct will have a template that lks like the mlecule belw.

5 Electrn-dnating grups make the diene mre reactive Alkyl grups dnate by inductin -O and OR grups dnate by resnance Nitrgen can dnate by resnance (as lng as it isn t NO2) Electrn-withdrawing grups make the dienphile mre reactive Carbnyl-cntaining grups Nitr grups Cyan-grups Sterechemistry f the Diels-Alder reactin Dienes can be described as being in either the s-cis cnfrmatinr the s- trans cnfrmatin s-cis s-trans s-trans is mre stable, but s-cis is necessary fr this reactin At the time f the reactin, the diene must be in the s-cis cnfrmatin. If there are substituents n either piece, sterechemistry is retained. What happens when the diene is in a ring? The ther carbn(s) f the ring get ut f the way f the reactin and frm a bridge.

6 The End Rule Mre truble than it s wrth! When yu start with a cyclic diene, there will be a bridge. If there are substituents n the dienphile, they will be trans t the bridge, if pssible. That s it. Cnjugatin and light Extended cnjugatin increases the wavelength f light absrbed. Remember that ROYGBIV is lwer t higher frequency, s it s really lnger t shrter wavelength. Nt terribly imprtant fr this curse.

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