Alkyne Addition Reactions

1)xs NaNH2 2)H2O Elimination

Makes alkyne from One X on each C of triple bond

xs HX

two X on first C with R

HX

double bond with X on first C with R

1) H2SO4, H2O 2)HgSO4 Acid-catalyzed hydration

Ketone

1) R2BH 2)H2O2, NaOH Hydroboration-oxidation

Aldehyde

1) X2(one equivalent) 2)CCl4 Halogenation

double bond with X added on each side

1)Excess X2 2)CCl4 Halogenation

two X on each C

1)O3 2)H2O Ozonolysis

terminal: 1 Carboxylic Acid + 1 CO2

Internal: 2 Carboxylic acid replaces triple bond

1)NaNH2 2)RX Alkylation

R' on the other side

1)Na 2)NH3 (l) Dissolving Metal Reduction

Trans double bond

1)H2 2)Pt Hydrogenation

remove triple bond to become single

1)H2 2)Lindlar's Catalyst Hydrogenation with Poisoned catalyst

Cis double bond