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Related Concept Videos

Introduction to Functional Groups02:08

Introduction to Functional Groups


Functional groups are group of atoms with specific chemical properties that occur within organic molecules and sometimes denoted as “R”. Functional groups are found along the carbon backbone of macromolecules can form chains or rings of carbon atoms. Functional groups can “functionalize” a compound by enabling it to adopt different physical and chemical properties.
Types of common functional groups
The table below summarizes some of the major functional groups in organic chemistry. (The...
Overview of Advanced Functional Groups02:22

Overview of Advanced Functional Groups


Functional groups are groups of atoms with specific chemical properties that occur within organic molecules and are sometimes denoted as “R”. Functional groups can “functionalize” a compound by enabling it to adopt different physical and chemical properties.
Types of Advanced Functional Groups
The table below summarizes some of the major functional groups in organic chemistry.
Carbocations02:10

Carbocations

Carbocations are one of the reaction intermediates formed during several nucleophilic substitutions or elimination reactions. A carbocation is an electron-deficient species with the central carbon atom having six electrons and three bonded atoms. The central carbon in a carbocation is sp2 hybridized with trigonal planar geometry. It has an empty p orbital perpendicular to the plane of the structure that can accept electrons. Thus, carbocations act as strong electrophiles and may react with any...
Properties of Organometallic Compounds01:23

Properties of Organometallic Compounds

Organometallic compounds are compounds that contain a carbon–metal bond. Carbon belongs to an organyl group like alkyl, aryl, allyl, or benzyl groups. The metal can be from Group I or Group II of the periodic table, a transition metal, or a semimetal.
C–C Bond Formation: Aldol Condensation Overview01:10

C–C Bond Formation: Aldol Condensation Overview

Aldol condensation is an important route in synthetic organic chemistry used to generate a new carbon–carbon bond under basic or acidic conditions. The aldol condensation reaction presented in Figure 1 constitutes an aldol addition reaction followed by the dehydration process.
C–C Bond Cleavage: Retro-Aldol Reaction00:57

C–C Bond Cleavage: Retro-Aldol Reaction

The reverse of the aldol addition reaction is called the retro-aldol reaction. Here, the carbon–carbon bond in the aldol product is cleaved under acidic or basic conditions to form two molecules of carbonyl compounds. The mechanism of the reaction consists of three steps.
In the first step, as depicted in Figure 1, the base deprotonates the β-hydroxy ketone at the hydroxyl group to form an alkoxide ion.

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Related Experiment Video

Updated: Jul 16, 2026

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)
06:34

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides (CHIPS)

Published on: June 20, 2014

Highly selective C-H functionalization/halogenation of acetanilide.

Xiaobing Wan1, Zhongxun Ma, Bijie Li

  • 1Beijing National Laboratory for Molecular Sciences, Peking University, Beijing 100871, China.

Journal of the American Chemical Society
|June 8, 2006
PubMed
Summary

This study introduces a new method for regioselective C-H functionalization and halogenation of acetanilides. Palladium and copper catalysts efficiently produce ortho-haloacetanilides using copper halides as the halogen source.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Halogenation

Background:

  • C-H functionalization is a key strategy in organic synthesis.
  • Regioselective halogenation of aromatic compounds is synthetically valuable.
  • Acetanilides are common structural motifs in pharmaceuticals and materials.

Purpose of the Study:

  • To develop a highly regioselective method for the ortho-halogenation of acetanilides.
  • To explore the use of palladium and copper catalysts in C-H functionalization reactions.
  • To identify efficient halogen sources for the transformation.

Main Methods:

  • The reaction employs palladium(II) acetate (Pd(OAc)2) and copper(II) acetate (Cu(OAc)2) as catalysts.
  • Copper(II) halides (CuX2) serve as the halogen source.
  • Acetanilides undergo direct C-H functionalization at the ortho position.

Main Results:

  • The catalytic system demonstrated high regioselectivity for ortho-halogenation.
  • The reaction efficiently produced a range of ortho-haloacetanilides.
  • The methodology offers a direct route to valuable halogenated intermediates.

Conclusions:

  • This work presents an effective palladium/copper-catalyzed method for regioselective C-H halogenation of acetanilides.
  • The developed protocol provides straightforward access to ortho-haloacetanilides.
  • The findings contribute to the advancement of C-H functionalization strategies in organic synthesis.