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Section 6 - 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 on 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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