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Related Concept Videos

SN1 Reaction: Stereochemistry02:15

SN1 Reaction: Stereochemistry

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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 electrophilic carbon and the leaving group ionizes to generate the carbocation intermediate. The second step of the mechanism is the nucleophilic attack.
In the formed carbocation, the positively charged carbon is sp2 hybridized with a trigonal planar geometry. As all the three substituents lie on the same plane, a plane of symmetry for the...
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SN1 Reaction: Kinetics02:05

SN1 Reaction: Kinetics

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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 the SN2 mechanism despite using a strong nucleophile.
However, Sir Christopher Ingold and Edward D. Hughes, who studied the kinetics of various nucleophilic substitution reactions, noticed that a tertiary alkyl halide does undergo a nucleophilic substitution reaction in the presence of a weak nucleophile. While studying the substitution...
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SN1 Reaction: Mechanism02:25

SN1 Reaction: Mechanism

14.4K
Kinetic studies of ionization of a tertiary halide in a protic solvent suggest that only the substrate participates in the rate-determining step (slow step). The nucleophile is involved only after the slowest step. The SN1 reaction takes place in a multiple-step mechanism. 
Firstly, the haloalkane ionizes to generate a carbocation intermediate and a halide ion. This heterolytic cleavage is highly endothermic with large activation energy. The ionization of the substrate, facilitated by a...
14.4K
Acidity of 1-Alkynes02:42

Acidity of 1-Alkynes

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The acidic strength of hydrocarbons follows the order: Alkynes > Alkenes > Alkanes. The strength of an acid is commonly expressed in units of pKa — the lower the pKa, the stronger the acid. Among the hydrocarbons, terminal alkynes have lower pKa values and are, therefore, more acidic. For example, the pKa values for ethane, ethene, and acetylene are 51, 44, and 25, respectively, as shown here.
11.3K
Predicting Products: SN1 vs. SN202:27

Predicting Products: SN1 vs. SN2

17.4K
Nucleophilic substitution reactions of alkyl halides can proceed via an SN1 or an SN2 mechanism. While in SN2 reactions, the nucleophile attacks the substrate simultaneously as the leaving group departs, in SN1 reactions, the substrate first dissociates to give the carbocation intermediate. Various factors such as the structure of the substrate, the strength of the nucleophile, and the nature of the solvent promote one mechanism over the other.
With increased substitution on the alkyl halide,...
17.4K
Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

4.7K
Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
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Practical Stability of Au25(SR)18-1/0/+1.

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  • 1Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.

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Summary

Superatom shell filling explains metal cluster stability, but solvent, atmosphere, and ligand shell also impact lifetime. A practical model integrates shell-closing and colloidal factors for predicting cluster decomposition pathways.

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Area of Science:

  • * Inorganic Chemistry
  • * Materials Science
  • * Physical Chemistry

Background:

  • * Superatom electron and geometric shell filling are key to the thermodynamic stability of coinage and alkali metal clusters.
  • * Factors beyond simple shell filling, such as solvent, atmosphere, and ligand shell, significantly influence the lifetime of ligated clusters in solution.

Purpose of the Study:

  • * To systematically present a practical stability model for ligated metal clusters.
  • * To incorporate both electronic/geometric shell-closing and colloidal stability aspects into the model.
  • * To elucidate the factors determining cluster decomposition pathways (fusion vs. fission).

Main Methods:

  • * Development of a 'practical' stability model for ligated metal clusters.
  • * Systematic analysis of factors influencing cluster stability and decomposition.
  • * Investigation of the role of solvent polarity in determining decomposition pathways.

Main Results:

  • * A comprehensive model for ligated metal cluster stability is proposed, integrating shell-filling and colloidal considerations.
  • * Cluster decomposition can occur via fusion or fission pathways.
  • * Solvent polarity is identified as a critical factor in directing the decomposition pathway.

Conclusions:

  • * Ligated metal cluster stability is governed by a combination of electronic/geometric shell closure and colloidal factors.
  • * The proposed practical model provides a framework for understanding and predicting cluster behavior.
  • * Understanding decomposition pathways is crucial for controlling cluster longevity and reactivity in solution.