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Related Concept Videos

Carbocations02:10

Carbocations

13.9K
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...
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Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

9.7K
The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
9.7K
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

5.0K
By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
5.0K
α-Alkylation of Ketones via Enolate Ions01:10

α-Alkylation of Ketones via Enolate Ions

3.9K
Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the...
3.9K
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

4.0K
Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group...
4.0K
Reactions of α-Halocarbonyl Compounds: Nucleophilic Substitution01:17

Reactions of α-Halocarbonyl Compounds: Nucleophilic Substitution

4.0K
Nucleophilic substitution in α-halocarbonyl compounds can be achieved via an SN2 pathway. The reaction in α-haloketones is generally carried out with less basic nucleophiles. The use of strong basic nucleophiles leads to the generation of α-haloenolate ions, which often participate in other side reactions.
4.0K

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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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Stable Carbocation Generated via 2,5-Cyclohexadien-1-one Protonation.

Craig Fraser1, Rowan D Young1

  • 1Department of Chemistry, National University of Singapore , 3 Science Drive 3, Singapore 117543, Singapore.

The Journal of Organic Chemistry
|December 6, 2017
PubMed
Summary
This summary is machine-generated.

Protonation of cyclohexadienone (1) generates carbocation [3]+, enabling hydride abstraction and oxidation. This carbocation

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Area of Science:

  • Organic Chemistry
  • Carbocation Chemistry

Background:

  • Cyclohexadienones are versatile organic compounds.
  • Carbocations are key intermediates in organic reactions.

Purpose of the Study:

  • To investigate the generation and reactivity of a novel carbocation from a substituted cyclohexadienone.
  • To explore the potential applications of this carbocation in organic synthesis.

Main Methods:

  • Protonation of substituted cyclohexadienone (1) using acids.
  • Structural analysis of the generated carbocation [3]+.
  • Evaluation of hydride abstraction and oxidation capabilities.

Main Results:

  • Successful generation of carbocation [3]+.
  • Structural similarity of [3]+ to known trityl carbocations.
  • Demonstrated potential for hydride abstraction and oxidation reactions.

Conclusions:

  • The novel carbocation [3]+ is readily accessible from stable precursors.
  • Its structural and reactive properties suggest broad applicability in trityl-based organic synthesis.