Nucleophilic Substitution Organic Substitution versus Inorganic Single Replacement
Nucleophilic Substitution Organic Substitution versus Inorganic Single Replacement Oxidation-reduction, with new ionic bonds, in single replacement Making and breaking covalent bonds in
organic substitution Aromatic and Acyl Substitution Addition/elimination that reconstitutes aromatic system
Addition/elimination that reconstitutes carbonyl group Radical Substitution Nucleophilic Substitution Bimolecular Nucleophilic
Substitution (SN2) Unimolecular Nucleophilic Substitution (SN1) Second Order with Inversion
First Order with Racemization SN2 Inversion versus SN1 Racemization SN2 Inversion SN1 Racemization
Stereospecific Loss of optical purity Kinetics of SN2 versus SN1 SN2
Rate = k[Substrate][Nucleophile] Rate depends on nucleophile conc. Restrictive collision orientation in RDS SN 1 Rate = k[Substrate] Rate independent of nucleophile conc.
Net bond dissociation in RDS Kinetic Control versus Thermodynamic Control Steric Hindrance versus Carbocation Stability
Less hindered substrate favors SN2 More stable carbocation favors SN1 Protic Solvents for SN2 versus SN1 Nucleophile stabilized in SN2
Charged intermediates stabilized in SN1 Protic versus Aprotic Solvents Effect of Nucleophile SN2 could be favored with superior nucleophiles:
Localized, destabilized anion Low electronegativity atom Larger, more polarizable atom
High p-character hybrid orbital Low steric hindrance Factors Favoring SN2 versus SN1 Less hindered substrates favor SN2; substrates with more stable carbocation intermediates favor SN1. Polar aprotic solvents, which avoid sequestration of
nucleophiles, are favored for SN2; protic solvents, which stabilize intermediates, are favored for SN1. Exceptional nucleophiles may improve the preference for SN2 over SN1.
- Luminous and non-luminous objects - History of light - The electromagnetic spectrum - Prisms - Colour . TeachWithFergy Preview File. Please enjoy this preview of your Power Point. Some slides appear blank because they have been removed.
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