ch 9 reactions of alkynes

1. xs NaNH2

2. H2O

elimination of an alkane to terminal alkyne

xs HX

hydrohalogenation

terminal alkyne to alkane

HX

hydrohalogenation

terminal alkyne to halogen and r group double bonded

HgSO4

H2SO4, H2O

acid-catalyzed hydration

terminal alkyne, to enol, to ketone

1. R2BH

2. H2O2, NaOH

hydroboration oxidation

terminal alkyne to aldehyde

X2 (one equiv)

CCl4

halogenation of terminal alkyne

xs X2

CCl4

halogenation

terminal alkyne to tetrahalide

1. O3

2. H2O

ozonolysis

terminal alkyne to carboxylic acid plus CO2

1. NaNH2

2. RX

alkylation

terminal alkyne to internal alkyne

Na

NH3

dissolving metal reduction

internal alkyne to trans alkene

H2

Pt

hydrogenation

internal alkyne to alkane

H2

lindlar's catalyst

hydrogenation

internal alkyne to cis alkene