Related Experiment Video

Updated: Jul 8, 2026

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
12:30

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework

Published on: April 9, 2018

Letter: Silver mediated ester bond formation in the gas phase: substrate structure is important

George N Khairallah, Tom Waters, Richard A J O'Hair

    European Journal of Mass Spectrometry (Chichester, England)
    |January 15, 2008
    PubMed

    More Related Videos

    Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy07:49

    Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy

    Published on: February 20, 2020

    Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks (MOFs)08:25

    Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks (MOFs)

    Published on: January 17, 2020

    Related Concept Videos

    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...
    E2 Reaction: Kinetics and Mechanism02:45

    E2 Reaction: Kinetics and Mechanism

    SN2 substitutions and E2 eliminations of alkyl halides proceed via a concerted pathway. While the nucleophile attacks the alpha carbon in SN2 reactions, it functions as a strong base and abstracts a beta hydrogen in the E2 mechanism. The rate-limiting transition state in E2 elimination reactions is characterized by partially broken carbon–hydrogen and carbon–halogen bonds and a partially formed pi bond between the alpha and beta carbons. The beta hydrogen and halide are eliminated...
    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: 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.
    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,...
    Regioselective Formation of Enolates01:33

    Regioselective Formation of Enolates

    As depicted in the figure below, the unsymmetrical ketones can form two possible enolates: less substituted or more substituted enolates. Usually, the thermodynamic enolates are formed from the more substituted α-carbon atom, while the kinetic enolates are formed faster by deprotonation from the less substituted position. The thermodynamic enolates have lower energy, so they are more stable. But the energy required to form kinetic enolates is less.