CHEM 282 Lecture Notes - Lecture 1: Heterocyclic Amine, Osteoporosis, Sulfonate
23 Mar 2018
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Hemiacetyl: comp that switches b/n an alcohol and ketone. Propene w bromine adds the halogen across the double bond at low temps but at high temps or low [halogen] sub occurs. Propene undergoes allylic bromination w n-bromosuccinimide (nbs) in presence of light or peroxide (o-o bond easily breaks and forms radical species) Nbs provides a low conc of br for radical rx, low conc favours allylic sub over alkene addition. Propagation step: br reacts w propene to prod an allylic radical and hbr, hbr reacts w. Nbs to prod bromine molecule which reacts w a propene radical to regen a bromine stability of allyl radical. Can be explained via molecular orbital theory or resonance theory. Allyl radical has two contributing resonance forms. Allyl cation is intermediate in stability b/n tertiary and secondary carbocation resonance rules. Resonance structures are not a true representation of the real structure.
