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Preparation of Amides

Preparation of Amides

Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...

Limitations of Friedel–Crafts Reactions

Limitations of Friedel–Crafts Reactions

Several restrictions limit the use of Friedel–Crafts reactions. First, the halogen in the alkyl halide must be attached to an sp3-hybridized carbon for the Friedel–Crafts reactions to occur. Vinyl or aryl halides do not react since the carbocations formed are unstable under the reaction conditions. Second, Friedel–Crafts alkylation is susceptible to carbocation rearrangement, and the major products obtained have a rearranged carbon skeleton. In contrast, the acylium ion is...

Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction

Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction

α-Substituted ketones or aldehydes can be synthesized from enamines by the Stork enamine reaction, named after its pioneer Gilbert Stork. Enamines are useful synthetic intermediates where the lone pair on nitrogen is in conjugation with the C=C bond. They resemble enolate ions, as the resonance forms of both species have a nucleophilic α carbon.

Aldehydes and Ketones to Alkenes: Wittig Reaction Overview

Aldehydes and Ketones to Alkenes: Wittig Reaction Overview

The Wittig reaction is the conversion of carbonyl compounds-aldehydes and ketones-to alkenes using phosphorus ylides, or the Wittig reagent. The reaction was pioneered by Prof. Georg Wittig, for which he was awarded the Nobel Prize in Chemistry.

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.

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Related Experiment Video

Updated: Nov 20, 2025

Light-driven Molecular Motors on Surfaces for Single Molecular Imaging

Light-driven Molecular Motors on Surfaces for Single Molecular Imaging

Published on: March 13, 2019

Ideality in Context: Motivations for Total Synthesis.

David S Peters¹, Cody Ross Pitts¹, Kyle S McClymont¹

¹Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.

Accounts of Chemical Research

|January 21, 2021

Summary

Total synthesis, a cornerstone of organic chemistry, has evolved from proving concepts to pursuing efficiency and simplicity. Modern efforts focus on innovative strategies to achieve "ideality" in molecule construction.

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Last Updated: Nov 20, 2025

Light-driven Molecular Motors on Surfaces for Single Molecular Imaging

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Published on: March 13, 2019

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

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Synthesis and Purification of Iodoaziridines Involving Quantitative Selection of the Optimal Stationary Phase for Chromatography

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Area of Science:

Organic Chemistry
Synthetic Chemistry

Background:

Total synthesis has a rich history, evolving from challenging vitalism to elucidating natural product structures.
The field has advanced from an intricate science and art form to a standardized process, enabling computer-aided design.
Modern total synthesis is driven by the pursuit of efficiency, scalability, and

Purpose of the Study:

To trace the evolution of total synthesis and its methodologies.
To highlight the shift towards simplicity and efficiency in contemporary natural product synthesis.
To showcase laboratory case studies demonstrating the pursuit of

Main Methods:

Review of historical developments in organic synthesis.
Analysis of strategies for natural product total synthesis.
Presentation of laboratory case studies from the past five years.

Main Results:

Demonstration of the field's progression towards greater sophistication and feasibility.
Emphasis on the modern focus on efficiency, scalability, and ideality over complexity.
Illustrations of innovative strategies for reducing step count and enhancing synthetic economy.

Conclusions:

Total synthesis remains a dynamic field attracting researchers with its challenges and creative opportunities.
The pursuit of simplicity and