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Chapter 6

Nucleophilic Substitution and Elimination Reactions of Alkyl Halides

Алкилгалоиды
Алкилгалоиды
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 ...
Реакции нуклеофильного замещения
Реакции нуклеофильного замещения
Historical perspective In 1896, the German chemist Paul Walden discovered that he could interconvert pure enantiomeric (+) and (-) malic acids through a ...
Нуклеофилы
Нуклеофилы
The word “nucleophile” has a Greek root and translates to nucleus-loving. Nucleophiles are either negatively charged or neutral species with a ...
Электрофилы
Электрофилы
This lesson explains the definition, classification, and characteristic features of an electrophile that are key features of nucleophilic substitution ...
Выход из групп
Выход из групп
The nature of leaving groups strongly influences the outcome of a nucleophilic substitution reaction. In general, in a nucleophilic substitution reaction, ...
Карбокатионы
Карбокатионы
Carbocations are one of the reaction intermediates formed during several nucleophilic substitutions or elimination reactions. A carbocation is an ...
<sub>Реакция S N</sub>2: Кинетика
Реакция S N2: Кинетика
Kinetic Studies and Significance In a chemical reaction, a relationship exists between the concentration of reactants and the rate at which the reaction ...
Реакция S<sub>N</sub>2: механизм
Реакция SN2: механизм
The kinetic studies of SN2 reactions suggest an essential feature of its mechanism: it is a single-step process without intermediates. Here, both the ...
Реакция S<sub>N</sub>2: Переходное состояние
Реакция SN2: Переходное состояние
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 ...
Реакция S<sub>N</sub>2: стереохимия
Реакция SN2: стереохимия
In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the ...
S<sub>N</sub>1 Реакция: кинетика
SN1 Реакция: кинетика
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 ...
S<sub>N</sub>1 Реакция: механизм
SN1 Реакция: механизм
Kinetic studies of ionization of a tertiary halide in a protic solvent suggest that only the substrate participates in the rate-determining step (slow ...
Реакция S<sub>N</sub>1: стереохимия
Реакция SN1: стереохимия
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 ...
Прогнозирование продуктов: S<sub>N</sub>1 vs. S<sub>N</sub>2
Прогнозирование продуктов: SN1 vs. SN2
Nucleophilic substitution reactions of alkyl halides can proceed via an SN1 or an SN2 mechanism. While in SN2 reactions, the nucleophile attacks the ...
Реакции элиминации
Реакции элиминации
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 ...
Реакция Е2: кинетика и механизм
Реакция Е2: кинетика и механизм
SN2 substitutions and E2 eliminations of alkyl halides proceed via a concerted pathway. While the nucleophile attacks the alpha carbon in SN2 reactions, ...
Реакция Е2: стереохимия и региохимия
Реакция Е2: стереохимия и региохимия
Elimination reactions of alkyl halides can yield one or more alkenes depending on the specific regiochemical and stereochemical considerations. While the ...
Реакция Е1: кинетика и механизм
Реакция Е1: кинетика и механизм
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 ...
Реакция Е1: стереохимия и региохимия
Реакция Е1: стереохимия и региохимия
One of the critical aspects of the E1 reaction mechanism, as also observed in E2, is the regiochemistry, with multiple regioisomers obtained as products. ...
Прогнозирование продуктов: замещение или элиминация
Прогнозирование продуктов: замещение или элиминация
When a nucleophile and an alkyl halide react, nucleophilic substitution and β-elimination reactions compete to generate products. The following ...
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