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Alkynyl Reaction Mechanisms (Additions and Products (Markovnikov Additions…
Alkynyl Reaction Mechanisms
Synthesis
Elimination of Hydrogen Halides
Geminal Dihalides + NaNH2 (strong base)
yields most substituted alkyne
Deprotonation
Acetylene + NaNH2 (strong bases or grignard reagents)
Sn2 Reactions with Electrophiles
Deprotonated Alkynes + Alkyl Halides
Additions and Products
Catalytic Hydrogenation
yields alkanes
Partial Hydrogenation
via Lindlar's Catalyst
yields cis (Z) alkenes
Dissolving Metal Reduction
via Na/NH3 (solvated e-)
yields trans (E) alkenes
Markovnikov Additions
Addition of HX
via 2 HX equivalent and carbocation formation
yields geminal dihalides
Addition of X2
first addition is trans, but yields alkanes
Acid-Catalyzed Hydration
via dilute acid in H2O
yields enols and ketones
Hydroboration
1) R2BH 2) NaOH, H2O2
yields aldehydes
Oxymercuration
via HgSO4 in dilute acid
yields ketones
Ozonolysis
monosubstituted alkynes
carboxylic acids and CO2
disubstituted alkynes
carboxylic acids