1|Page

REACTIONS OF ALKYNES

Addition Reactions
o Similar to addition to alkenes
o Pi bond becomes two sigma bonds.
o Usually exothermic
o One or two molecules may add.

Addition of Hydrogen

Three reactions:
o Add lots of H2 with metal catalyst (Pd, Pt, or Ni) to reduce alkyne to alkane, completely
saturated.

o Use a special catalyst, Lindlar’s catalyst to convert an alkyne to a cis-alkene.

2|Page

Example:

o React the alkyne with sodium in liquid ammonia to form a trans-alkene.

Example:

Addition of Halogens
3|Page

Addition of HX

Addition of HBr with Peroxides

Hydration of Alkynes
4|Page

Hydroboration - Oxidation

Oxidation of Alkynes
o Similar to oxidation of alkenes.
o Dilute, neutral solution of KMnO4 oxidizes alkynes to a diketone.

o Warm, basic KMnO4 cleaves the triple bond.

o Ozonolysis, followed by hydrolysis, cleaves the triple bond.

O O
(1) O3
CH3 C C CH2 CH3 CH3 C OH + HO C CH2 CH3
(2) H2O