Reagents in Orgo for AlkYnes

NaNH₃

OR

Na^Ø

NH₃

Trans reduction

H2, Lindlar’s cat.

Cis reduction

H2/Pt

OR

H₂

Pd/C

Full reduction from alkyne to alkane

1) BH3, THF

2) H2O2, NaOH

1) Hydroboration

2) Oxidation

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

1) THF OR 9-BBN

2) H₂O₂, NaOH