Chapter 11 Substitution Reactions

A nucleophile was defined as a species that donates two electrons to carbon to form a new covalent σ-bond. Using a Lewis base analogy, a nucleophile is a two-electron donor, but the product is not an “ate” complex. Nucleophiles react with a variety of molecules that have electrophilic carbon atoms in a reaction where one atom or group replaces another. When iodide and bromomethane collide, the energy transferred must be equal to the energy of activation in order to initiate a SN2 reaction. The polar and protic water can be contrasted with an aprotic solvent. The SN2 reaction is one of the more important transformations in organic chemistry since one functional group can be transformed into a different functional group. Halide ions are important nucleophiles to interconvert the halogen of alkyl halides.

Nucleophiles

Defining SN2 Reactions

Pentacoordinate Transition State

Substitution and Structure

Solvent Effects in SN2 Reactions

Alkyl Halides & Sulfonate Esters

Functional Group Transformations. Halide and 0 Nucleophiles

Functional Group Transformations. N and C Nucleophiles

Ionization ofTertiary Halides

The SN1 Reaction

Stereochemistry and SN1 Reactions

Rearrangement and SN1 Reactions

Alcohols React H-X Acids

SNi Reactions

Ethers React with Strong Acids

Epoxides React By SN2 and SN1 Reactions

Radical Halogenation

Rate of Substitution of Difticrent H Atoms

Radical Bromination of Alkanes

Allylic Halogenation

Mitsunobu Reaction

Alkyne Coupling