Chapter 9 alkyne rxns

Elimination - Geminal

Uses xs NaNH2 and H2O, X2 are on the same carbon - made into alkyne

Elimination - Vicinal

Uses xs NaNH2 and H20, X2 are on opposite carbons - made into alkyne

Hydrohalogenation - 2 equivalents

Markovnikov addition, uses xs HX

Hydrohalogenation - 1 equivalent

Markovnikov addition, uses HX, 1 equivalent

Acid catalyzed hydration

Markovnikov addition, addition of H-OH, uses HgSO4, H20 and H2SO4, forms an enol that taut to ketone

Hydroboration-oxidation

Anti-Markovnikov addition, forms an aldehyde, uses R2BH and H202 and NaOH

Halogenation - 1 equivalent

Anti (trans) addition, uses X2 and CCl4

Halogenation - 2 equivalents

uses X2 and CCl4

Ozonolysis

Formation of a carboxylic acid or CO2 (CO2 is formed from terminal alkyne, any other alkyne forms a carboxylic acid)

Alkylation

Formation of a Nu: and E+ (terminal C: -), uses NaNH2 and whatever group needs put on the end

Dissolving metal reduction

Anti (trans) addition, alkyne to alkene, uses Na* and NH3

Hydrogenation

Addition of H2, alkyne to alkane

Hydrogenation with poisoned catalyst

Cis alkene, uses H2 and lindlar catalyst