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Alkyne —H-X→
1 X added across double bond
Alkyne —2(H-X)→
Alkane with 2 X’s
Alkyne —X2→
2 X’s add trans
Alkyne —2(X2)→
This monstrosity

Alkyne —H2O, HgSO4, H2SO4→
Ketone

Alkyne —1) (sia)2BH, 2) H2O2, NaOH→
Aldehyde

Alkyne —2(H2), Pd/C→
Alkane
Alkyne —H2, Lindlar’s catalyst→
Z-alkene

Alkyne —2(Na°), NH3(l)→
E-alkene

Alkyne —NaNH2 + SN2 substrate→
Alkyne + extended carbon chain
Alkyne —NaNH2, ketone, 2) H3O+→
Alcohol with triple bond
Alkene —X2, 2(NaNH2), H2O→
Alkyne
Alkyne-H —cold KMnO4, H2O→
keto acid

Alkyne —cold KMnO4, H2O
diketone

Alkyne —warm KMnO4 →
Carboxylic acid
Alkyne —cold KMnO4, H2O→
2 carboxylic acids
Alkyne-H —1) cold O3, 2) H2O→
Carboxylic acid + formic acid
Alkyne —1) cold O3, 2) H2O→
Two carboxylic acids