Alkynes Flashcards
Hydrohalogenation
Alkyne + HX –> trans alkene
trans alkene + HX –> geminal halide (geminal:gemini: twins)
Halogenation
Alkyne + X2 –> trans alkene
trans alkene + X2 –> tetra halide
Acid-Catalyzed Hydration
Alkyne + acid –> enol –> ketone
Hydroboration-oxidation
Alkyne –> ketone
if TERMINAL Alkyne –> aldehyde
Catalytic Hydrogenation (Reduction)
- Synthesis of alkanes
- Synthesis of cis-alkenes
- Synthesis of trans-alkenes
Synthesis of alkanes
+H2 and Pt in excess converts alkynes to alkanes
+2 moles H2 and Pd converts alkynes to alkanes
Synthesis of cis-alkenes
Alkyne +H2 + Lindlar’s catalyst + Ni2B –> cis alkene
Synthesis of trans-alkenes
Alkyne + H2 + Na/Li in NH3 in low temp –> trans alkene
Lindlar’s Catalyst
P-2 or metallic Pd deposited in CaCO3
Oxidation of Alkynes
- Ozonolysis
2. Oxidation in KMnO4
Ozonolysis
+ O3 –>
- nonterminal alkynes : 2 carboxylic acids
- terminal alkynes: 1 carboxylic acid and 1 carbonic acid
Oxidation in KMnO4
+hot +basic +KMnO4 –> carboxylic acid + CO2
Synthesis of Alkynes
- Dehydrohalogenation of vicinal dihalides