From page 251 of your text: advice and warning

Drill and practice with reactions of alkenes The 4 main classes of reactions of alkene are: (U-Pick) a)elimination, substitution, allylic addition, rearrangement b)SN1, SN2, E1 and E2 c)Carbocation addition, bridgehead addition, free radical addition and organometallic/redox reactions d)Radical substitution, SN1, E2 and allylic rearrangement In a carbocation addition, addition proceeds: a)To make rearranged alkene b)Anti-Markovnikoff, inverted c)Markovnikoff, inverted d)Markovnikoff, racemic Which class of reactions of alkenes always involves Br 2 in CCl 4 or ether ? Bridgehead (halohydrin) mechanism

Free radical additions are characterized by: a)Absence of peroxides and markovnikoff addition b)Formation of rings and unsaturated produces c)Presence of peroxides and markovnikoff substitution d)Presence of peroxides and anti-markovnikoff substitution Key intermediate state in halohydrin reactions : a)Sp 2 Carbocation b)Free radical c)3-atom semi-carbocation d)5-coordinate complex Which reaction class(es) can produce larger dimers, trimers…polymers a) bridgehead b) Organometallic /redox c) radical d) carbocation Which reaction class includes reactions that aren’t additions ? Organometallic (ozonolysis and allylic substitutions)

Term Anti addition Reaction class Bridgehead (halohydrin) Anti Markovnikoff additionRadical 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 Markovnikoff addition carbocation

>95% yield 100% Mark. Br 2 CCl 4 wet H2OH2O H+/reflux Hg(OAc) 2 in THF NaBH 4 /OH-

Syn diol Product name ? Etc…

KOH + majorminor ethanol Run an ozonolysis O3O3 Zn/H + Run the anti-Markovnikoff Brown 2 step preparation of alcohols B 2 H 6 neat H 2 O 2 with OH -

ether What’s my common name ? diazomethane

Metal amalgamOrganic halide What’s my reaction name? CH 2 I 2 Zn(Cu) Simmons-Smith insertion H2H2 Pt, Pd, Rh, or Ni

An epoxide Anti-diol Industrial route to isopropanol ??? Besides cold KMnO 4, what other reagent allows us to make a syn diol ? OsO 4

Final product above is ……. Anti diol A different route to anti diol Peroxide/formic acid (makes hydroperoxide) Starting from any alkene, make 3-bromo-1-butene in one step

I love Organic Chemistry ! It makes people cry.