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Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism01:14

Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism

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The Wittig reaction, which converts aldehydes or ketones to alkenes using phosphorus ylides, proceeds through a nucleophilic addition‒elimination process.
The reaction begins with the nucleophilic addition between a phosphorus ylide and the carbonyl compound. Due to its carbanionic character,  phosphorus ylide acts as a strong nucleophile and attacks the electrophilic carbonyl group. This generates a charge-separated dipolar intermediate called betaine. The negatively charged oxygen atom and...
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Carboxylic Acids to Acid Chlorides01:18

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Carboxylic acids react with SOCl2 or PCl5 to form acid chlorides. Amongst the carboxylic acid derivatives, acid chlorides are the most reactive and synthetically important derivatives. They are useful reagents for Friedel–Crafts acylation of some aromatic compounds.
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α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction01:15

α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction

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The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the...
3.0K
Aldehydes and Ketones to Alkenes: Wittig Reaction Overview01:19

Aldehydes and Ketones to Alkenes: Wittig Reaction Overview

7.8K
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.
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Hybridization of Atomic Orbitals II03:35

Hybridization of Atomic Orbitals II

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sp3d and sp3d 2 Hybridization
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The Phosphorus Cycle01:21

The Phosphorus Cycle

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Unlike carbon, water, and nitrogen, phosphorus is not present in the atmosphere as a gas. Instead, most phosphorus in the ecosystem exists as compounds, such as phosphate ions (PO43-), found in soil, water, sediment and rocks. Phosphorus is often a limiting nutrient (i.e., in short supply). Consequently, phosphorus is added to most agricultural fertilizers, which can cause environmental problems related to runoff in aquatic ecosystems.
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Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus
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A Greener Vision for P-C Bond Formation

Kelsie E Wentz1, Rebekka S Klausen1

  • 1Department of Chemistry, Johns Hopkins University, 3400 N. Charles Street, Baltimore, Maryland 21218, United States.

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