Organic Chemistry (Alkene Reactions)

Reagents: HBr (or HCl, HI)

What's Added: H⁺ & Br⁻

Regioselectivity: Markovnikov

Sterioselectivity: -

Intermediate: Carbocation

Rearrangements: Possible

Reaction: Hydrohalogenation

Reagents: H₃O⁺

What's Added: H⁺ & OH⁻

Regioselectivity: Markovnikov

Sterioselectivity: -

Intermediate: Carbocation

Rearrangements: Possible

Reaction: Hydration

Reagents: H⁺, ROH

What's Added: H⁺ & OR⁻

Regioselectivity: Markovnikov

Sterioselectivity: -

Intermediate: Carbocation

Rearrangements: Possible

Reaction: Addition of Alcohol

Reagents: Br₂/CCl₄ (or Cl₂)

- CCl₄ & Cl₂ are Inert

What's Added: Br⁺ & Br⁻

Regioselectivity: -

Sterioselectivity: Anti Addition

Intermediate: Bromonium Ion

Reaction: Bromination

Reagents: Br₂/H₂O (or Cl₂/H₂O)

What's Added: Br⁺ & OH⁻ (or Cl⁺ & OH⁻)

Regioselectivity: Markovnikov

Sterioselectivity: Anti Addition

Intermediate: Bromonium Ion

Reaction: Bromination in H₂O

Reagents: Br₂/ROH (Cl₂/ROH)

What's Added: Br⁺ & OR⁻ (or Cl⁺ & OR⁻)

Regioselectivity: Markovnikov

Sterioselectivity: Anti Addition

Intermediate: Bromonium Ion

Reaction: Bromination in Alcohol

Reagents: 1. Hg(OAc)₂, H₂O

2. NaBH₄

What's Added: H⁺ & OH⁻

Regioselectivity: Markovnikov

Sterioselectivity: Anti Addition

Intermediate: Mercurinium Ion

Reaction: Oxymercuration-Demurcuration

Reagents: 1. Hg(OAc)₂, ROH

2. NaBH₄

What's Added: H⁺ & OR⁻

Regioselectivity: Markovnikov

Sterioselectivity: Anti Addition

Intermediate: Mercurinium Ion

Reaction: Alkoxymercuration-Demercuration

Reagents: 1. BH₃∙THF

2. H₂O₂, OH⁻, H₂O

What's Added: H⁺ & OH⁻

Regioselectivity: Anti-Markovnikov

Sterioselectivity: Syn Addition (H⁺ & OH⁻ are Syn)

Intermediate: -

Reaction: Hydroboration-Oxidation

Reagents: H₂/Catalyst

(Catalyst = Pt/C, Pd/C, or Ni)

What's Added: H & H

Regioselectivity: -

Sterioselectivity: Syn Addition

Intermediate: -

[Forms Meso Compound]

Reaction: Catalytic Hydrogenation (Catalytic Reduction)

Reagents: HBr/ROOR (Peroxide)

What's Added: H∙ & Br∙ Regioselectivity: Anti-Markovnikov

Sterioselectivity: -

Intermediate: Radical

Reaction: Hydrobromination w/ Peroxide

Reagents: 1. RCO₃H (MCPBA)

2. H₃O⁺

What's Added: OH & OH

Regioselectivity: -

Sterioselectivity: Anti Addition

Intermediate: Epoxide

Reaction: Anti-Hydroxylation

Reagents: 1. RCO₃H (or MCPBA)

What's Added: OH & OH

Regioselectivity: -

Sterioselectivity: Anti Addition

Intermediate: Epoxide

Reaction: Epoxidation

Reagents: 1. OsO₄

2. H₂O₂

What's Added: OH & OH

Regioselectivity: -

Sterioselectivity: Syn Addition

Intermediate: -

[Forms Meso Compound]

Reaction: Syn-Hydroxylation

Reagents: KMnO₄ (cold, dilute)/ OH⁻

What's Added: OH & OH

Regioselectivity: -

Sterioselectivity: Syn Addition

Intermediate: -

[Forms Meso Compound]

Reaction: Syn Hydroxylation

Reagents: KMnO₄ (hot, conc.)/ H₃O⁺

What's Added: Cleave double bond and add OH to less substituted C.

Reaction: Oxidative Clevage

Reagents: 1. O₃

2. H₂O₂ (Peroxide)

What's Added: Cleave double bond and add OH to less substituted C.

Reaction: Ozonolysis (under Oxidizing Conditions)

Reagents: 1. O₃

2. (CH₃)₂S or (Zn/H₂O)

What's Added: Cleave double bond and add H (Aldehyde) to less substituted C

Reaction: Ozonolysis (Under Reducing Conditions)