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Chapter 6

Nucleophilic Substitution and Elimination Reactions of Alkyl Halides

אלקיל הלידס
אלקיל הלידס
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 ...
תגובות החלפה נוקלאופיליות
תגובות החלפה נוקלאופיליות
Historical perspective In 1896, the German chemist Paul Walden discovered that he could interconvert pure enantiomeric (+) and (-) malic acids through a ...
נוקלאופילים
נוקלאופילים
The word “nucleophile” has a Greek root and translates to nucleus-loving. Nucleophiles are either negatively charged or neutral species with a ...
אלקטרופילים
אלקטרופילים
This lesson explains the definition, classification, and characteristic features of an electrophile that are key features of nucleophilic substitution ...
עזיבת קבוצות
עזיבת קבוצות
The nature of leaving groups strongly influences the outcome of a nucleophilic substitution reaction. In general, in a nucleophilic substitution reaction, ...
קרבוקטיונים
קרבוקטיונים
Carbocations are one of the reaction intermediates formed during several nucleophilic substitutions or elimination reactions. A carbocation is an ...
S<sub>N</sub>2 תגובה: קינטיקה
SN2 תגובה: קינטיקה
Kinetic Studies and Significance In a chemical reaction, a relationship exists between the concentration of reactants and the rate at which the reaction ...
S<sub>N</sub>2 תגובה: מנגנון
SN2 תגובה: מנגנון
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 תגובה: מצב מעבר
SN2 תגובה: מצב מעבר
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 ...
S<sub>N</sub>2 תגובה: סטריאוכימיה
SN2 תגובה: סטריאוכימיה
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 תגובה: קינטיקה
SN1 תגובה: קינטיקה
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 תגובה: מנגנון
SN1 תגובה: מנגנון
Kinetic studies of ionization of a tertiary halide in a protic solvent suggest that only the substrate participates in the rate-determining step (slow ...
S<sub>N</sub>1 תגובה: סטריאוכימיה
SN1 תגובה: סטריאוכימיה
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 ...
חיזוי מוצרים: S<sub>N</sub>1 לעומת S<sub>N</sub>2
חיזוי מוצרים: SN1 לעומת SN2
Nucleophilic substitution reactions of alkyl halides can proceed via an SN1 or an SN2 mechanism. While in SN2 reactions, the nucleophile attacks the ...
תגובות אלימינציה
תגובות אלימינציה
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 ...
תגובת E2: קינטיקה ומנגנון
תגובת E2: קינטיקה ומנגנון
SN2 substitutions and E2 eliminations of alkyl halides proceed via a concerted pathway. While the nucleophile attacks the alpha carbon in SN2 reactions, ...
תגובת E2: סטריאוכימיה ורגיוכימיה
תגובת E2: סטריאוכימיה ורגיוכימיה
Elimination reactions of alkyl halides can yield one or more alkenes depending on the specific regiochemical and stereochemical considerations. While the ...
תגובת E1: קינטיקה ומנגנון
תגובת E1: קינטיקה ומנגנון
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 ...
תגובת E1: סטריאוכימיה ורגיוכימיה
תגובת E1: סטריאוכימיה ורגיוכימיה
One of the critical aspects of the E1 reaction mechanism, as also observed in E2, is the regiochemistry, with multiple regioisomers obtained as products. ...
חיזוי מוצרים: החלפה לעומת חיסול
חיזוי מוצרים: החלפה לעומת חיסול
When a nucleophile and an alkyl halide react, nucleophilic substitution and β-elimination reactions compete to generate products. The following ...
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