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Addition Reaction. Addition Reactions: Addition to Alkenes.

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Presentation on theme: "Addition Reaction. Addition Reactions: Addition to Alkenes."— Presentation transcript:

1 Addition Reaction

2 Addition Reactions: Addition to Alkenes

3 Addition Reactions: HX to Alkenes General Order of HX Reactivity: HI > HBr > HCl > HF Usually Dissolved in Solvent (CH 3 CO 2 H, CH 2 Cl 2 )

4 Addition Reactions: HBr to Alkenes 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?

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

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

7 Markovnikovs 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

8 H 2 SO 4 Addition to Alkenes

9 Alcohols From Alkyl Hydrogen Sulfates HYDROLYSIS Reaction of Alkyl Hydrogen Sulfate Simply Heat the Sulfate in Water Net Reaction is Markovnikov Addition of H 2 O to Alkene Used in One Industrial Ethanol Making Process

10 Addition of H 2 O to Alkenes: Hydration HYDRATION Reaction of an Alkene

11 Addition of Cl 2 and Br 2 to Alkenes

12 General Mechanism of Dihalide Addition

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


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