Addition Reaction.

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Presentation transcript:

Addition Reaction

Addition Reactions: Addition to Alkenes

Addition Reactions: HX to Alkenes General Order of HX Reactivity: HI > HBr > HCl > HF Usually Dissolved in Solvent (CH3CO2H, CH2Cl2)

Addition Reactions: HBr to Alkenes p Bond (Nucleophile) Protonate  Carbocation Intermediate Carbocation Captured by Br¯ (Nucleophile)  HBr Added HBr (or other HX) Addition in Two Overall Steps H+ and Carbocation are the Respective Electrophiles This is a SYMMETRIC Alkene  ASYMMETRIC ALKENES?

Markovnikov’s Rule: HBr to Alkenes 2-Bromopropane is Major Product Only Very Small Amount of 1-Bromopropane Observed True With Other Alkenes

Markovnikov’s Rule: Why? Product Distribution Explained When Looking at Intermediates Consider Carbocation Stability (2° > 1°) Major Product Formed From More Stable C+ Intermediate

Markovnikov’s Rule: C+ Stability We Know 2° Carbocations More Stable Than 1° Major Product Formed From More Stable C+ Intermediate Means TS in 2° Carbocation Pathway Lower in Energy Lower Energy of Activation Activation Energies in 1° Carbocation Pathways Much Larger

H2SO4 Addition to Alkenes

Alcohols From Alkyl Hydrogen Sulfates HYDROLYSIS Reaction of Alkyl Hydrogen Sulfate Simply Heat the Sulfate in Water Net Reaction is Markovnikov Addition of H2O to Alkene Used in One Industrial Ethanol Making Process

Addition of H2O to Alkenes: Hydration HYDRATION Reaction of an Alkene

Addition of Cl2 and Br2 to Alkenes

General Mechanism of Dihalide Addition

Anti-Markovnikov HBr Addition Addition of Peroxides (ROOR)  ANTI-MARKOVNIKOV Goes Through a Radical Mechanism

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