alkyne reactivity

addition of h-x

• turns into alkene

• markovnikov

• in excess, turns into alkane (but that second part of the rxn is slower)

hydrogenation

• adding H2 and Pd/C turns it to an alkane

• using lindlars catalyst turns it into a z/cis alkene

acid catalyzed hydration

• markovnikov

• turns alkyne into a carbonyl

• tautomerization: enol in equilibrium with a carbonyl (carbonyl is favored)

hydroboration/oxidation

• alkyl to carbonyl

• antimarkovnikov

• used disiamylborane in step 1 then NaOH and HOOH in step 2