Alkene/Alkyne Reactions and Synethesis

Start: Alkene
Reagents: H₂, Pd/Pt/Ni

Product: Alkane (syn addition)
Name: Catalytic Hydrogenation

Start: Alkene

Product: Alkane (syn addition)

Reagents: H₂, Pd/Pt/Ni

Name: Catalytic Hydrogenation

H₂, Pd/Pt/Ni

Start: Alkene
Reagents: HX (HCl, HBr, HI)

Product: Alkyl halide (Markovnikov)
Name: Hydrohalogenation

Start: Alkene

Product: Alkyl halide (Markovnikov)

Reagents: HX (HCl, HBr, HI)

Name: Hydrohalogenation

HX

Start: Alkene
Reagents: H₂O/H₂SO₄

Product: Alcohol (Markovnikov)
Name: Acid-Catalyzed Hydration

Start: Alkene
Product: Alcohol (Markovnikov)

Reagents: H₂O/H₂SO₄

Name: Acid-Catalyzed Hydration

H₂O/H₂SO₄

Start: Alkene
Reagents: 1) Hg(OAc)₂, H₂O 2) NaBH₄

Product: Alcohol (Markovnikov, NO rearrangements)
Name: Oxymercuration–Reduction

Start: Alkene
Product: Alcohol (Markovnikov, NO rearrangements)

Reagents: 1) Hg(OAc)₂, H₂O 2) NaBH₄

Name: Oxymercuration–Reduction

1) Hg(OAc)₂, H₂O 2) NaBH₄, NaOH

Start: Alkene
Reagents: 1) BH₃·THF 2) H₂O₂, OH⁻

Product: Alcohol (Anti-Markovnikov, syn)
Name: Hydroboration–Oxidation

Start: Alkene
Product: Alcohol (Anti-Markovnikov, syn)

Reagents: 1) BH₃·THF 2) H₂O₂, OH⁻
Name: Hydroboration–Oxidation

1) BH₃·THF 2) H₂O₂, OH⁻

Start: Alkene
Reagents: X₂ (like Br₂ or Cl₂)

Product: Vicinal dihalide (anti)
Name: Halogenation

Start: Alkene
Product: Vicinal dihalide (anti)

Reagents: X₂ (like Br₂ or Cl₂)
Name: Halogenation

Br₂

Start: Alkene
Reagents: Br₂ + H₂O

Product: Halohydrin (anti, OH on more substituted C)
Name: Halohydrin Formation

Start: Alkene

Product: Halohydrin (anti, OH on more substituted C)

Reagents: X₂ + H₂O

Name: Halohydrin Formation

X₂ + H₂O

Start: Alkene
Reagents: mCPBA

Product: Epoxide
Name: Epoxidation

Start: Alkene

Product: Epoxide

Reagents: mCPBA

Name: Epoxidation

mCPBA

Start: Alkene
Reagents: OsO₄ (or cold KMnO₄)

Product: Vicinal syn diol
Name: Syn Dihydroxylation

Start: Alkene

Product: Vicinal syn diol

Reagents: OsO₄ (or cold KMnO₄)

Name: Syn Dihydroxylation

OsO₄, H₂S

Start: Alkene
Reagents: O₃ → (CH₃)₂S or Zn/H₂O

Product: Aldehydes/Ketones
Name: Ozonolysis

Start: Alkene
Product: Aldehydes/Ketones

Reagents: O₃ → (CH₃)₂S or Zn/H₂O
Name: Ozonolysis

1) O₃, 2) H₂O₂

Start: Alkyl halide
Reagents: Strong base (OH⁻, OEt⁻, t-BuOK)

Product: Alkene

Name: Dehydrohalegenation

Start: Alkyl halide

Product: Alkene

Reagents: Strong base (OH⁻, OEt⁻, t-BuOK)

Name: Dehydrohalegenation

NaOH/t-BuOK

Start: Alcohol
Reagents: H₂SO₄ + heat

Product: Alkene

Name: Dehydration

Start: Alcohol

Product: Alkene

Reagents: H₂SO₄ + heat

Name: Dehydration

H₂SO₄ + heat

Start: Alkyne
Reagents: H₂, Lindlar

Product: Cis-alkene

Name: Cis Reduction

Start: Alkyne
Product: Cis-alkene

Reagents: H₂, Lindlar

Name: Cis Reduction

H₂, Lindlar

Start: Alkyne
Reagents: Na/NH₃

Product: Trans-alkene

Name: Trans Reduction

Start: Alkyne
Product: Trans-alkene

Reagents: Na/NH₃

Name: Trans Reduction

Na/NH₃

Start: Alkyne
Reagents: H₂, Pd/Pt/Ni

Product: Alkane

Name: Complete Reduction

Start: Alkyne
Product: Alkane

Reagents: H₂, Pd/C

Name: Complete Reduction

H₂, Pd/Pt/Ni

Start: Terminal alkyne
Reagent: NaNH₂

Product: Acetylide ion

Name: Deprotonation

Start: Terminal alkyne
Product: Acetylide ion

Reagent: NaNH₂

Name: Deprotonation

NaNH₂