Aliphatic Electrophilic Substitution

Lesson Structure

1.1         Objectives

1.2         Introduction

1.3         Unimolecular Substitution Reactions (S_E1)

1.3.1     Evidence for the S_E1 mechanism

1.3.2     Stereochemistry of S_E1 reaction

1.4         Bimolecular Substitution Reaction (S_E2)

1.4.1     S_E2 (Front) and S_E2 (Back): Evidence and Stereochemistry

1.4.2     S_Ei mechanism: Evidence and Stereochemistry

1.5         Electrophilic substitution accompanied by double bond shift

1.6         Effect of various factors on aliphatic electrophilic substitution

1.6.1     Effect of substrate

1.6.2     Effect of leaving group

1.6.3     Effect of solvent

1.7         Migration of double bond

1.7.1     Base catalysed double bond migration

1.7.2     Acid catalysed double bond migration

1.8         Some examples of aliphatic electrophilic substitution reactions

1.8.1     Halogenations of aldehydes and ketones

1.8.1a   Mechanism of base catalysed halogenations

1.8.1b   Mechanism of acid- catalysed halogenations

1.8.2     Halogenations of carboxylic acids and acyl halides

1.8.3     Halogenation of sulphoxide and sulphones

1.8.4     Aliphatic Diazonium coupling

1.8.5     Diazo transfer reaction

1.8.6     Nitrosation at Carbon (C-Nitrosation)

1.8.7     Nitrosation at Nitrogen (N-Nitrosation)

1.8.8     Addition – Elimination mechanism

1.8.8.1 Acylation at an aliphatic carbon

1.9         Some Naming Reaction of Aliphatic Substitution

1.9.1     Hell-Volhard-Zelinskii reaction

1.9.2     The Stork- Enamine reaction

1.9.3     Haloform reaction

1.10 Summary

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