SECTION 6 ² REACTIONS AND SYNTHESIS OF ALKENES 6-1 -- Addition of Halogens (X2) x Stereochemistry (Anti-Addition Observed) x Bromonium Ion Intermediate x Nucleophilic Solvent (H2O) vs. Inert Solvent (CCl4) 6-2 -- Halohydrin Formation x Use of Hypobromous Acid (HO-Br) x Anti-Addition of ²Br and ²OH 6-3 -- Hydration Reactions x Conversion of Alkenes to Alcohols x Markovnikov Regiochemistry x Acid-Catalyzation of Hydration Reactions x The Principle of Microscopic Reversibility 6-5 -- Oxymercuration Reaction x Markovnikov Addition of ²H and -OH x Use of NaBH4 as a Source of Hydride (:H-) x No Carbocation Rearrangements Observed x Hydride Shift 6-6 -- Hydroboration Reaction x Borane, BH3 x Replacing Borane·s ²H·s with Alkyl Groups (Substitution) x Mechanism for Hydroboration is ´Concertedµ x Reaction of BH3 with the Solvent Tetrahydrofuran (THF) x Steric Effects Control the Regiochemistry of the Observed Products x Syn-Addition (´Cisµ-like) 6-9 -- Non-Markovnikov Addition of HBr x Does Not Work with the Reagents HCl or HI x Free-Radical Chain Mechanism x Initiation and Propagation Steps of the Mechanism x 3° Radical vs. 1° Radical Intermediates (Stability) x Radical Stabilities x Polymer Production (Teflon, Polystyrene, Polyvinylchloride [PVC], and Plexiglass) 6-11 -- Catalytic Hydrogenation Reaction x Syn-Addition of H2 Across a Double-Bond 6-11 -- Hydroxylation Reaction x Conversion of an Alene to a Diol 6-12 -- Oxidative Cleavage Reactions x The Ozonolysis Reaction www.OChemNotes.com x Permanganate Reactions (MnO4-) 6-12 -- Carbene Additions Across a Double Bond x Their Use in Producing 3-Membered Rings x How Carbenes are Generated 6-13 -- The Simmons-Smith Reaction x Carbenoids x Zn(Cu) = ´Zn-Cuµ Couple 6-14 -- Periodic Acid Cleavage x Cleavage of Diols to Produce 2 Carbonyl Compounds www.OChemNotes.com SECTION 6 – REACTIONS AND SYNTHESIS OF ALKENES Were the FREE Section 6 Notes Useful? Want the FULL VERSION of the Section 6 Notes? Download Them Instantly for Only $6.99 at: OChemNotes.com www.OChemNotes.com