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Alkyne + (1. NaNH2/Et2O 2. RI)

Alkyne + (H2; Lindlar Pd - EtOH)

Catalytic Hydrogenation (Stops at alkene)

Markovnikov Oxidation

Na/NH3

NaNH2/Et2O

Alkyne + (H2; Pd/C - EtOH)

Alkyne + (H2O, H2SO4, HgSO4)

Deprotonation

Br replaces H on C next to alkene

1. BH3/THF 2. H2O2, NaOH, H2O

NBS/CCl4/heat

Benzene Ring, -OH something + (H2SO4)

Catalytic Hydrogenation (All the way)

Attach R to Alkyne

Anti-Markovnikov Oxidation

Alkyne to Alkene (Trans)

loss of -OH, attachment to ring