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Related Concept Videos

SN2 Reaction: Mechanism02:27

SN2 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 nucleophile and the substrate participate in the rate-determining step.
The presence of the more electronegative halogen in the substrate creates a polarized carbon-halide bond. The halide pulls the electron cloud generating an electrophilic center at the carbon atom. Thus, the carbon atom carries a partial positive charge while the halide has a...
SN2 Reaction: Transition State02:26

SN2 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 between the substrate and the halide occurs simultaneously through a transition state without forming an intermediate.
When the nucleophile approaches the electrophilic carbon with its lone pairs, the halide acts as a leaving group and moves away with the electron-pair bonded to the carbon. Dotted partial bonds represent the bonds being formed or broken...
SN2 Reaction: Stereochemistry02:23

SN2 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 the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
If the substrate is an achiral molecule at the α-carbon, the inversion of configuration is not observed.
SN1 Reaction: Mechanism02:25

SN1 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 (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 polar...
SN1 Reaction: Stereochemistry02:15

SN1 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 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...
Predicting Products: SN1 vs. SN202:27

Predicting Products: 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 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,...

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Related Experiment Video

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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
06:31

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

Published on: November 27, 2015

A SN2 reaction that avoids its deep potential energy minimum.

Lipeng Sun1, Kihyung Song, William L Hase

  • 1Department of Chemistry, Wayne State University, Detroit, MI 48202, USA.

Science (New York, N.Y.)
|May 4, 2002
PubMed
Summary

Most trajectories in the OH- + CH3F reaction bypassed the predicted intermediate, directly forming products. This suggests inefficient intramolecular vibrational energy redistribution (IVR) due to molecular structure, impacting chemical dynamics simulations.

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Area of Science:

  • Physical Chemistry
  • Chemical Dynamics
  • Computational Chemistry

Background:

  • The SN2 nucleophilic substitution reaction is a fundamental process in chemistry.
  • Understanding reaction mechanisms at the atomic level is crucial for predicting chemical behavior.
  • Statistical theories often assume intermediate complex formation and complete energy redistribution.

Purpose of the Study:

  • To investigate the atomic-level mechanisms of the OH- + CH3F SN2 reaction.
  • To explore the dynamics of the reaction trajectory from the central barrier to products.
  • To assess the role of intramolecular vibrational energy redistribution (IVR) in this reaction.

Main Methods:

  • Utilized chemical dynamics trajectory simulations.
  • Employed ab initio direct dynamics to simulate reaction pathways.
  • Analyzed the potential energy surface and trajectory behavior.

Main Results:

  • The reaction dynamics were simulated from the central barrier to products.
  • A deep minimum was observed in the product exit channel due to a hydrogen-bonded complex.
  • Over 90% of trajectories avoided this minimum, dissociating directly to products, contrary to statistical theory predictions.

Conclusions:

  • The majority of reactive trajectories did not form a long-lived intermediate.
  • This suggests inefficient intramolecular vibrational energy redistribution (IVR) is influenced by molecular structure.
  • Findings may apply to other reactive systems with inefficient IVR and hierarchical timescales.