Carbocationic Reaction Intermediates: Factors that influence carbocation formation Nature of the leaving group Structural factors Solvent effects Salt.

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Presentation transcript:

Carbocationic Reaction Intermediates: Factors that influence carbocation formation Nature of the leaving group Structural factors Solvent effects Salt effects Isotope effects

Factors that influence carbocation formation Nature of the leaving group

Factors that influence carbocation formation Anionic leaving groups

Factors that influence carbocation formation Structural factors

Factors that influence carbocation formation Solvent effects Solvent effects : Any property of a solvent system that can lower the energy of activation for heterolytic bond cleavage will favor carbocation formation.

The role of solvent in carbocation formation Dielectric constant - a rough measure of the ability of the solvent to separate oppositely charged ions. Dielectric constant - a rough measure of the ability of the solvent to separate oppositely charged ions. Hydrogen-bonding ability Hydrogen-bonding ability Acid-base properties Acid-base properties Nucleophilicity: As the nucleophilicity of a solvent decreases, the likelihood of discrete carbocation formation increases. Nucleophilicity: As the nucleophilicity of a solvent decreases, the likelihood of discrete carbocation formation increases.

Salt Effects: Ionic Strength As the ionic concentration of a solvent system increases, the overall polarity of the medium increases. Increased solvent polarity favors ionization of neutral molecules.

Common Ion (Mass Law) Effect

Special Salt Effect

Factors that influence carbocation formation Isotope effects

Nature of some carbocationic intermediates Stability of the intermediate

Stereochemistry of Carbocations

Stereochemistry of carbocations

Kinetics of carbocation formation

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