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Related Concept Videos

meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H

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All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for...
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2° Amines to N-Nitrosamines: Reaction with NaNO201:20

2° Amines to N-Nitrosamines: Reaction with NaNO2

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Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
5.5K
SN2 Reaction: Kinetics02:14

SN2 Reaction: Kinetics

10.3K
Kinetic Studies and Significance
In a chemical reaction, a relationship exists between the concentration of reactants and the rate at which the reaction proceeds. The study to measure this relationship is known as the kinetics of a chemical reaction. Kinetic studies are used to deduce the rate law of a chemical reaction, which provides information about the species involved during the transition state of the rate-determining step. Thus, kinetic studies help to derive the mechanism of a...
10.3K
SN2 Reaction: Mechanism02:27

SN2 Reaction: Mechanism

17.5K
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...
17.5K
SN2 Reaction: Transition State02:26

SN2 Reaction: Transition State

12.0K
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...
12.0K
SN2 Reaction: Stereochemistry02:23

SN2 Reaction: Stereochemistry

11.8K
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...
11.8K

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Related Experiment Video

Updated: Feb 6, 2026

Elucidating the Metabolism of 2,4-Dibromophenol in Plants
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2-Chloro-N-(2,4-dimethyl-phen-yl)acetamide.

B Thimme Gowda, Sabine Foro, Hartmut Fuess

    Acta Crystallographica. Section E, Structure Reports Online
    |January 5, 2011
    PubMed
    Summary

    The N-H bond conformation in C(10)H(12)ClNO is syn to the ortho methyl group. Molecules form chains via intermolecular N-H⋯O hydrogen bonds, similar to related acetanilides.

    Area of Science:

    • Organic Chemistry
    • Crystallography
    • Molecular Structure

    Background:

    • Acetanilides are a significant class of organic compounds with diverse applications.
    • Understanding the conformational preferences of substituents is crucial for predicting chemical properties and reactivity.
    • Previous studies have characterized various substituted acetanilides, providing a basis for comparison.

    Purpose of the Study:

    • To elucidate the molecular structure and conformation of the title compound, C(10)H(12)ClNO.
    • To compare the N-H bond conformation with related substituted acetanilides.
    • To investigate the intermolecular interactions governing the crystal packing.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the three-dimensional structure.

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  • Geometric parameters were analyzed and compared to known acetanilide structures.
  • Intermolecular interactions, specifically hydrogen bonding, were identified and characterized.

    • Main Results:

    • The N-H bond in C(10)H(12)ClNO adopts a syn conformation relative to the ortho methyl group.
    • This conformation is analogous to those observed in 2-chloro-N-(3-methyl-phenyl)acetamide and 2-chloro-N-(2-chloro-phenyl)acetamide.
    • The determined geometric parameters are consistent with those typically found in acetanilide derivatives.
    • Crystal structure analysis revealed the formation of chains through intermolecular N-H⋯O hydrogen bonds.

    Conclusions:

    • The study confirms the syn conformation of the N-H bond in C(10)H(12)ClNO, influenced by the ortho methyl group.
    • The observed hydrogen bonding pattern dictates the crystal packing and molecular assembly.
    • The findings contribute to the understanding of structure-property relationships in substituted acetanilides.