Section 7 - Alkynes
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Alkynes - Section 7 of Organic Chemistry Notes is 12 pages in length (page 7-1 through page 7-12) and covers ALL you'll need to know on the following lecture/book topics:
7-1 -- Definition, Bond Length, and BDE of Alkynes
7-1 -- Alkyne Nomenclature
· “-yne” Ending
· Alkenynes – Compounds Having Both Double Bonds and Triple Bonds
· Alkynl Substituents (Branches)
7-2 -- Stabilities of Alkynes
· Alkyl Groups (-R) Stabilize Triple Bonds
· Terminal Alkynes vs. Internal Alkynes
· Cycloalkynes
7-3 -- Hydration of Alkynes
· Markovnikov Addition of H2O
· Tautomerization
· Use of Hg2+ as a Catalyst
7-5 -- Addition of HX Across the Triple Bond
· Markovnikov Regiochemistry
· The –H and –X Add Trans
· Two Consecutive Markovnikov Additions of HX are Observed
7-5 -- Addition of X2 Across the Triple Bond
· X2 = Cl2 or Br2
· Mixtures of Products (Cis and Trans)
7-6 -- Hydroboration
· Non-Markovnikov Addition of H2O
· Internal Alkynes vs. Terminal Alkynes
· Internal Alkynes and Increased Steric Hindrance
· Terminal Alkynes and Use of Disiamyl Borane
· Tautomerization is Observed
7-7 -- Addition of H2 Across a Triple Bond – 2 Ways
· Catalytic Hydrogenation
· Use of the “Lindlar Catalyst”
· Syn-Addition Gives Cis Product (Catalytic Hydrogenation)
· Reduction of Alkynes with Li (or Na) in NH3(l)
· Anti-Addition Gives Trans Product (Reduction Reaction)
7-8 -- Alkylation of Terminal Alkynes
· The “Acetylide Ion” as a Nucleophile
· pKA of Alkynes
· Use of Sodamide (NaNH2)
7-10 -- Oxidative Cleavage of Alkynes
· Zn(Cu) = “Zn-Cu” Couple
· Formation of 2 Carboxylic Acids
· Use of KMnO4 and H3O+
7-10 -- Synthesis of Organic Compounds
· “Working Backwards” When Given a Final Product to Synthesize
7-11 -- Retrosynthetic Analysis
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