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Chapter 6

Nucleophilic Substitution and Elimination Reactions of Alkyl Halides

Alkyl Halides
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine,…
Nucleophilic Substitution Reactions
Historical perspective In 1896, the German chemist Paul Walden discovered that he could interconvert pure enantiomeric (+) and (-) malic acids…
Nucleophiles
The word “nucleophile” has a Greek root and translates to nucleus-loving. Nucleophiles are either negatively charged or neutral species…
Electrophiles
This lesson explains the definition, classification, and characteristic features of an electrophile that are key features of nucleophilic…
Leaving Groups
The nature of leaving groups strongly influences the outcome of a nucleophilic substitution reaction. In general, in a nucleophilic substitution…
Carbocations
Carbocations are one of the reaction intermediates formed during several nucleophilic substitutions or elimination reactions. A carbocation is an…
S<sub>N</sub>2 Reaction: Kinetics
In a chemical reaction, a relationship exists between the concentration of reactants and the rate at which the reaction proceeds. The study to…
S<sub>N</sub>2 Reaction: Mechanism
The kinetic studies of SN2 reactions suggest an essential feature of its mechanism: it is a single-step process without intermediates. Here, both the…
S<sub>N</sub>2 Reaction: Transition State
An SN2 reaction of an alkyl halide is a single-step process in which bond formation between the nucleophile and the substrate and bond breaking…
S<sub>N</sub>2 Reaction: Stereochemistry
In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As…
S<sub>N</sub>1 Reaction: Kinetics
In an SN2 reaction, the reaction rate depends on both the type of nucleophile and the substrate. A hindered tertiary alkyl halide is practically…
S<sub>N</sub>1 Reaction: Mechanism
Kinetic studies of ionization of a tertiary halide in a protic solvent suggest that only the substrate participates in the rate-determining step…
S<sub>N</sub>1 Reaction: Stereochemistry
This lesson provides an in-depth discussion of the stereochemical outcomes in an SN1 reaction. In the first step of an SN1 reaction, the bond between…
Predicting Products: S<sub>N</sub>1 vs. S<sub>N</sub>2
Nucleophilic substitution reactions of alkyl halides can proceed via an SN1 or an SN2 mechanism. While in SN2 reactions, the nucleophile attacks the…
Elimination Reactions
A nucleophile can react with an alkyl halide to give the substitution product by displacing the halogen. Or it can function as a base to give the…
E2 Reaction: Kinetics and Mechanism
SN2 substitutions and E2 eliminations of alkyl halides proceed via a concerted pathway. While the nucleophile attacks the alpha carbon in SN2…
E2 Reaction: Stereochemistry and Regiochemistry
Elimination reactions of alkyl halides can yield one or more alkenes depending on the specific regiochemical and stereochemical considerations. While…
E1 Reaction: Kinetics and Mechanism
Here, in contrast to the E2 reaction mechanism, we delve into the aspects of the E1 reaction mechanism, which has two steps: rate-limiting loss of…
E1 Reaction: Stereochemistry and Regiochemistry
One of the critical aspects of the E1 reaction mechanism, as also observed in E2, is the regiochemistry, with multiple regioisomers obtained as…
Predicting Products: Substitution vs. Elimination
When a nucleophile and an alkyl halide react, nucleophilic substitution and β-elimination reactions compete to generate products. The following…
Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyl(tropone)iron
aza-Michael adducts of tricarbonyl(tropone)iron are synthesized by two different methods. Primary aliphatic amines and cyclic secondary amines…
Improved In-gel Reductive &#946;-Elimination for Comprehensive O-linked and Sulfo-glycomics by Mass Spectrometry
Separation of proteins by SDS-PAGE followed by in-gel proteolytic digestion of resolved protein bands has produced high-resolution proteomic analysis…
Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Bicyclic aziridinium ions were generated by the removal of an appropriate leaving group through internal nucleophilic attack by nitrogen atom in the…

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