Alkynes

Synthesis internal Alkynes (alkyne forming)

NaNH₂ (strong base)

Synthesis terminal Alkyne (Alkyne forming)

NaNH₂

Alkyne hydrogenation (+H alkyne —> alkene)

1. H₂

2. Pd

Alkyne Hydrogenation ONLY Cis alkene (+H alkyne —> alene) 

1. H₂

2. Lindlars Catalyst 

Alkyne dissolving metal reductive hydrogenation (trans alkenes Na wants to be Na⁺)

1. Na

2. NH₃

Hydrohalogenation of Alkyne markovnikov (Alkyne —> alkane with X+H) 

HBr

Radical hydrohalogenation (antimarkov) adds H-Br (alkyne —> alkene) 

1. HBr 

2. ROOR

Mercury Catalyzed Hydration created a ketone (2 methyls, to carbon, to double bonded O)

1. HgSO₄

2. H₃O⁺(H₂SO₄ + H₂O)

Hydroboration Oxidation adds double bonded O

1. R₂BH

2. H₂O₂, NaOH

Halogenation Antiaddition for trans alkene

Cl₂

Ozonolysis internal alkyne forms 2 carboxylic acids double donded O, and OH,

on terminal alkyne forms 1 COO and 1 CO2

1. O_3. 

2. H₂O

Radical chlorination methane - chnages 1 H to X

• polychlorination excess changes all H to X 

1. Cl₂

2. hv 

Allylic Bromination H to Br (H that is adjacent to double CC bond)

• forms radicals of br and also forms br2 

1. NBS 

2. hv