Alkynes
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Alkynes. Reaction Acidity Synthesis. s- Complex of Acetylene. p- Bonds. Hydrocarbon Comparison. Alkyne Nomenclature. Enes with Ynes. Catalytic Hydrogenation. Lindlar’s Catalyst. H 2 on a Poisoned Catalyst Prevents Over-Reduction cis Alkenes. Addition of HX. Br 2 Addition.

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Alkynes

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Alkynes

Reaction

Acidity

Synthesis


s-Complex of Acetylene

p-Bonds


Hydrocarbon Comparison


Alkyne Nomenclature


Enes with Ynes


Catalytic Hydrogenation


Lindlar’s Catalyst


H2 on a Poisoned CatalystPrevents Over-Reductioncis Alkenes


Addition of HX


Br2 Addition


Hydration: OxymercurationMarkovnikov


Enol – Keto TautomerizationIntermolecular


Oxymercuration Mechanism


Hydration: HydroborationAnti-Markovnikov


Hydroboration Mechanism


Draw the Products


Acidity of Terminal Alkynes


Acetylide Formation


Alkylation of Acetylide IonsHomologations using SN2 rxn


Multi-step Syntheses


Retrosynthetic AnalysisBegin with the Product


Fill in the Reagents


How Many Steps?


5 Steps


Compound A, C9H12, absorbs 3 equivalents of H2 on catalytic reduction over palladium to give B, C9H18. On reaction with acidic KMnO4, compound A gives, among other things, a ketone that was identified as cyclohexanone. On treatment with NaNH2 in NH3, followed by addition of iodomethane, compound A gives a new hydrocarbon C, C10H14. What are the structures of A, B and C?


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