ALIPHATIC NUCLEOPHILIC SUBSTITUTION

Lesson Structure

1.0       Objectives

1.1       Introductions

1.1.1    Leaving groups as (or leaving) nucleophiles or nucleofuge

1.1.2    Incoming nucleophile  

1.2.      Mechanism SN² Reaction

1.3.      The SN¹ mechanism (carbocation process)

1.3.1    Evidence for the SN¹ mechanism

1.4.      Mixed SN¹ and SN² mechanism

1.5.      SNⁱ mechanism

1.6.      SET mechanism

1.6.1    Evidence for SET mechanism:

1.7.      Neighbouring Group Participation (Intramolecular Nucleophilic Displacement)

1.8.      Classical and Non- Classical Carbocation (bridged carbocations)

1.9.      Carbocation Rearrangements

1.10.    Norbornyl systems

1.11.    Norbornyl cation

1.12.    Nucleophilic substitution at an allylic carbon

1.13.    Nucleophilic substitution at an aliphatic trigonal carbon

1.14.    Nucleophilic substitution at vinylic carbon

1.15.    Structure & Reactivity Analysis of Nucleophilic Substitution Reactions

1.16.    HSAB principle

1.16.1  HSAB Principle 

1.16.2  HSAB & FMO Analysis  

1.16.3  Characteristics of Hard, Soft & Borderline Acids & Bases

1.16.4  Applications of HSAB Principle

1.17.    Ambident Nucleophiles

1.18.    Summary

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