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Related Concept Videos

Acid Halides to Esters: Alcoholysis01:12

Acid Halides to Esters: Alcoholysis

Alcoholysis is a nucleophilic acyl substitution reaction in which an alcohol functions as a nucleophile. Acid halides react with alcohol to produce esters. The mechanism proceeds in three steps:
Alkylation of β-Diester Enolates: Malonic Ester Synthesis01:14

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides01:16

Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides

Naming Acid Halides
The IUPAC and common names of acid halides are derived from the corresponding carboxylic acids, by changing “ic acid” to “yl halide.” For example, as shown below, the IUPAC name ethanoyl chloride is derived from ethanoic acid, and the common name, acetyl chloride, is obtained from acetic acid.
Direct-Acting Cholinergic Agonists: Pharmacokinetics01:31

Direct-Acting Cholinergic Agonists: Pharmacokinetics

Direct-acting cholinergic agonists, such as synthetic choline esters and naturally occurring alkaloids, exert their effects by enhancing the actions of acetylcholine and stimulating the parasympathetic nervous system. Synthetic choline esters share structural similarities with acetylcholine. For example, they have a positively charged quaternary ammonium or onium group, contributing to their hydrophilic characteristics. As a result, they are poorly absorbed in the body through oral...
Esters to β-Ketoesters: Claisen Condensation Overview01:24

Esters to β-Ketoesters: Claisen Condensation Overview

Regular Claisen condensation is a base-promoted reaction involving identical esters with two α hydrogens, condensing to produce β-ketoesters. It is a nucleophilic acyl substitution reaction wherein one of the ester molecules, upon deprotonation by the base, forms a nucleophilic enolate ion, while the other molecule serves as an electrophile.
Acid Halides to Ketones: Gilman Reagent01:14

Acid Halides to Ketones: Gilman Reagent

Lithium dialkyl cuprate, also known as Gilman reagents, selectively reduces acid halides to ketones. The acid chloride is treated with Gilman reagent at −78 °C in the presence of ether solution to produce a ketone in good yield.
As shown below, the mechanism proceeds in two steps. First, one of the alkyl groups of the reagent acts as a nucleophile and attacks the acyl carbon of the acid chloride to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen double...

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Related Experiment Video

Updated: Jun 1, 2026

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
06:52

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile

Published on: October 30, 2018

Glycine methyl ester hydro-chloride.

Sérgio M F Vilela, Filipe A Almeida Paz, João P C Tomé

    Acta Crystallographica. Section E, Structure Reports Online
    |May 18, 2011
    PubMed
    Summary

    This study reveals how (methoxy-carbonyl-methyl)ammonium chloride forms supramolecular tapes through strong hydrogen bonds. These tapes then pack together in the solid state via weaker interactions.

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    Microwave-assisted Functionalization of Poly(ethylene glycol) and On-resin Peptides for Use in Chain Polymerizations and Hydrogel Formation

    Published on: October 29, 2013

    Area of Science:

    • Solid-state chemistry
    • Supramolecular chemistry
    • Crystallography

    Background:

    • Understanding the self-assembly of organic salts is crucial for materials science.
    • The role of non-covalent interactions in crystal engineering is an active area of research.

    Purpose of the Study:

    • To elucidate the crystal structure and intermolecular interactions of (methoxy-carbonyl-methyl)ammonium chloride.
    • To investigate the formation and packing of supramolecular assemblies in the solid state.

    Main Methods:

    • Single-crystal X-ray diffraction analysis.
    • Analysis of hydrogen bonding and other non-covalent interactions.

    Main Results:

    • The title compound crystallizes as a salt, C(3)H(8)NO(2)(+)·Cl(-).
    • Strong N(+)-H⋯Cl(-) hydrogen bonds form directional supramolecular tapes parallel to the c axis.
    • Tapes pack via weaker C-H⋯O interactions and van der Waals forces.

    Conclusions:

    • The crystal structure is dictated by a combination of strong hydrogen bonds and weaker interactions.
    • (Methoxy-carbonyl-methyl)ammonium chloride serves as a model for understanding crystal growth and supramolecular assembly.