Reactions and Synthesis of Alkenes

Reactions and Synthesis of Alkenes -- Section 6 of Organic Chemistry Notes is 14 pages in length (page 6-1 through page 6-14) and covers ALL you'll need to know about the following lecture/book topics:

SECTION 6 – Reactions and Synthesis of Alkenes

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

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Reactions and Synthesis of Alkenes

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