Alkene and Alkyne Reactions

Acid-Catalyzed Hydration (Markovnikov)

Typical Reagents: Dilute Acid (H₂SO₄, H₃PO₄, etc.)

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Addition of Hydrogen Halides to Alkenes (Markovnikov)

Typical Reagents: HX

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Addition of Halogen (Anti-addition, stereospecific). Vicinal Dihalide forms.

Typical Reagents: X₂ and CCl₄

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Formation of Vicinal Halohydrin (Anti-addition, stereospecific)

Typical Reagents: X₂ and H₂O

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Hydroboration Oxidation (Anti-Markovnikov, Syn-addition, stereospecific). 

Typical Reagents 1.) BH₃ ^. THF and 2.) H₂O₂/KOH

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Reduction via Catalytic Hydrogenation (syn-addition, think of it as reducing double bond to nothing)

Typical Reagents: H₂, Pd, Pt, PtO₂ etc. (Catalysts and H₂)

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Direct Epoxidation (stereospecific and syn addition)

Typical Reagents: MCPBA, CH₂Cl₂

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Indirect Epoxidation.

1.) Formation of Vicinal Halohydrin

2.) Add Strong Base

Typical Reagents: 1.) X₂, H₂O and 2.) KOH

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Syn Hydroxylation

Typical Reagents: OsO₄ and NMO^.H₂O

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Anti-Hydroxylation

Typical Reagents: Dilute Acid (H₃O⁺ and H₂O)

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Ozonolysis

Typical Reagents:

1.)O₃ and 2.) (CH₃)₂S or H₂O/Zn

or

Cleavage of Vicinal Diol

1.) Syn Hydroxylation

2.) NaIO₄

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