CHEM 233 Lecture Notes - Lecture 18: Nucleophilic Substitution, Relative Permittivity, Dielectric
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3-10 depending on the nature of r), ch3o (pka ch3oh 16); enolates of mono-carbonyl compounds (pka 20 25), etc. Exposure to basic nucleophiles causes only elimination by the e2 mechanism: nucleophiles may be classified as: Such compounds possess a high dielectric constant, r. Meeting of oct 18: 2 the electrostatic force f between two charges, q1 and q2, separated by a distance r and embedded in a medium (gas, liquid, or solid), is (coulomb equation): R = dielectric constant of the medium: such polar media facilitate the dissociation of the alkyl halide into a halide ion and a carbocation by diminishing the electrostatic attractive force between the two ions. Ch3: following dissociation of the alkyl halide, a suitable non-basic nucleophile can combine with the carbocation, leading to a product of substitution of halogen. The above two-step mechanism (dissociation + capture of the carbocation) is described as an sn1 reaction.
