PRACTICE, PRACTICE, PRACTICE

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PRACTICE, PRACTICE, PRACTICE How do you master Organic Chemistry (and get a good grade) ?? PRACTICE, PRACTICE, PRACTICE

Drill and practice with reactions of alkenes (the re-run) The 4 main classes of reactions of alkene are: (U-Pick) elimination, substitution, allylic addition, rearrangement SN1, SN2, E1 and E2 Carbocation addition, bridgehead addition, free radical addition and organometallic/redox reactions Radical substitution, SN1, E2 and allylic rearrangement In a carbocation addition, addition proceeds: To make rearranged alkene Anti-Markovnikoff, inverted Markovnikoff, inverted Markovnikoff, racemic Which class of reactions of alkenes always involves Br2 in CCl4 or ether ? Bridgehead (halohydrin) mechanism

Free radical additions are characterized by: Absence of peroxides and markovnikoff addition Formation of rings and unsaturated produces Presence of peroxides and markovnikoff substitution Presence of peroxides and anti-markovnikoff substitution Key intermediate state in halohydrin reactions : Sp2 Carbocation Free radical 3-atom semi-carbocation 5-coordinate complex Which reaction class(es) can produce larger dimers, trimers…polymers c) radical d) carbocation b) Organometallic /redox a) bridgehead Which reaction class includes reactions that aren’t additions ? Organometallic (ozonolysis and allylic substitutions)

Anti addition Term Reaction class Bridgehead (halohydrin) Anti Markovnikoff addition Radical addition Syn and anti; H.C. Brown, peroxy acids and NBS Organometallic/redox Dimers and trimers; industrial route to ethanol carbocation Polymerization; carbene insertion; freon additions Radical addition carbocation Markovnikoff addition

CCl4 wet Br2 H+/reflux H2O Hg(OAc)2 in THF NaBH4 /OH- >95% yield 100% Mark.

Product name ? Syn diol Etc…

KOH + Run an ozonolysis O3 Zn/H+ ethanol major minor Run the anti-Markovnikoff Brown 2 step preparation of alcohols B2H6 neat H2O2 with OH-

Final question ….

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