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NaNH3
OR
NaØ
NH3
Trans reduction
H2, Lindlar’s cat.
Cis reduction
H2/Pt
OR
H2
Pd/C
Full reduction from alkyne to alkane
1) 2 equiv. NaNH2
1) Deprotonation
If there is no step 2, the Na+ binds to the C-
Li as an ion bound to C
Analogous with Na
2)
LDA
???
Au+
H2O
Hydration
1) O3
2) H2O
(terminal C)
Ozonolysis
adds