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Chapter 6

Nucleophilic Substitution and Elimination Reactions of Alkyl Halides

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Structural Properties Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as …
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Historical perspective In 1896, the German chemist Paul Walden discovered that he could interconvert pure enantiomeric (+) and (-) malic acids through a …
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The word “nucleophile” has a Greek root and translates to nucleus-loving. Nucleophiles are either negatively charged or neutral species with a …
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This lesson explains the definition, classification, and characteristic features of an electrophile that are key features of nucleophilic substitution …
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The nature of leaving groups strongly influences the outcome of a nucleophilic substitution reaction. In general, in a nucleophilic substitution reaction, …
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Carbocations are one of the reaction intermediates formed during several nucleophilic substitutions or elimination reactions. A carbocation is an …
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Kinetic Studies and Significance In a chemical reaction, a relationship exists between the concentration of reactants and the rate at which the reaction …
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The kinetic studies of SN2 reactions suggest an essential feature of its mechanism: it is a single-step process without intermediates. Here, both the …
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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 between …
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In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the …
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In an SN2 reaction, the reaction rate depends on both the type of nucleophile and the substrate. A hindered tertiary alkyl halide is practically inert to …
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Kinetic studies of ionization of a tertiary halide in a protic solvent suggest that only the substrate participates in the rate-determining step (slow …
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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 the …
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Nucleophilic substitution reactions of alkyl halides can proceed via an SN1 or an SN2 mechanism. While in SN2 reactions, the nucleophile attacks the …
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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 …
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SN2 substitutions and E2 eliminations of alkyl halides proceed via a concerted pathway. While the nucleophile attacks the alpha carbon in SN2 reactions, …
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Elimination reactions of alkyl halides can yield one or more alkenes depending on the specific regiochemical and stereochemical considerations. While the …
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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 the …
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One of the critical aspects of the E1 reaction mechanism, as also observed in E2, is the regiochemistry, with multiple regioisomers obtained as products. …
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When a nucleophile and an alkyl halide react, nucleophilic substitution and β-elimination reactions compete to generate products. The following …
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Separation of proteins by SDS-PAGE followed by in-gel proteolytic digestion of resolved protein bands has produced high-resolution proteomic analysis of …
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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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aza-Michael adducts of tricarbonyl(tropone)iron are synthesized by two different methods. Primary aliphatic amines and cyclic secondary amines participate …