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Related Concept Videos

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.
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...
Prochirality02:05

Prochirality

The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
Enolate Mechanism Conventions01:15

Enolate Mechanism Conventions

When a carbonyl compound is treated with a strong base, the α position gets deprotonated to give a resonance-stabilized intermediate called an enolate. Enolates are ambident nucleophiles because they possess two nucleophilic sites that can attack an electrophile owing to the delocalization of the negative charge between the α carbon and oxygen atoms. When the oxygen atom attacks an electrophile, it is called O-attack, whereas electrophilic attack via the α carbon is known as C-attack.
C-attack...
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...
Chirality at Nitrogen, Phosphorus, and Sulfur02:30

Chirality at Nitrogen, Phosphorus, and Sulfur

Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...

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Related Experiment Video

Updated: May 28, 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

Innate and guided C-H functionalization logic.

Tobias Brückl1, Ryan D Baxter, Yoshihiro Ishihara

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

Accounts of Chemical Research
|October 25, 2011
PubMed
Summary
This summary is machine-generated.

This study introduces two categories of C-H functionalization: guided and innate. Harnessing innate reactivity offers efficient synthesis strategies for complex molecules, benefiting organic and medicinal chemists.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Catalysis

Background:

  • C-H functionalization converts C-H bonds to C-X bonds, a fundamental chemical transformation.
  • The broad definition of C-H functionalization necessitates clearer categorization for synthetic planning.

Purpose of the Study:

  • To distinguish between "guided" and "innate" C-H functionalization logic.
  • To demonstrate the utility of these descriptors in analyzing reactivity and planning synthesis.
  • To showcase applications in synthesizing complex molecules like terpenes and alkaloids.

Main Methods:

  • Categorization of C-H functionalization into "guided" (directed by external factors) and "innate" (driven by substrate reactivity).
  • Application of these concepts to analyze existing and develop new synthetic methodologies.
  • Synergistic use of both guided and innate strategies for complex molecule synthesis.

Main Results:

  • Demonstrated successful application of innate reactivity for unique bond constructions, enabling rapid total syntheses.
  • Achieved controlled synthesis of terpene families using a combination of guided and innate functionalizations.
  • Developed novel chemoselective innate C-H functionalization protocols for synthesizing nitrogen-rich alkaloids and forging C-C bonds.

Conclusions:

  • The distinction between guided and innate C-H functionalization is a valuable conceptual tool for synthetic strategy.
  • Harnessing innate reactivity provides efficient pathways for complex molecule synthesis.
  • Strategic application of C-H functionalization logic significantly enhances synthetic efficiency for organic and medicinal chemists.