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Related Concept Videos

Solvents01:12

Solvents

71.9K
A solvent is a substance, most often a liquid, that can dissolve other substances. Here, the substance being dissolved is called a solute. When a solvent and a solute combine, they form a solution - a homogenous mixture of both the solvent and the solute. Water is a universal biological solvent. Its polar structure allows it to dissolve many other polar compounds. The ability of water to dissolve is governed by a balance between water molecules binding to each other and binding to the solute.
A...
71.9K
Titration in Nonaqueous Solvents01:16

Titration in Nonaqueous Solvents

1.5K
Most acid-base titrations are performed in an aqueous medium. In aqueous titrations, water competes with weaker acids or bases for proton donation or acceptance, leading to ambiguous endpoints in the titration curve. Water also affects the partial ionization of weak acids or bases. For example, water accepts a proton from acetic acid to form hydronium and acetate ions. The hydronium ion formed is a stronger acid than acetic acid, and the acetate ion is a stronger base than water. As a result,...
1.5K
Solvating Effects02:12

Solvating Effects

9.2K
An understanding of the solvating effect helps rationalize the relation between solvation and acidity of the compound. In addition, this also explains the relative stability of conjugate bases for compounds with different pKa values. This lesson details, in-depth, the principle of solvating effects. The strength of an acid and the stability of its corresponding conjugate base are determined using pKa values. This observed relationship is a consequence of solvation, which is the interaction...
9.2K
Leveling Effect and Non-Aqueous Acid-Base Solutions02:11

Leveling Effect and Non-Aqueous Acid-Base Solutions

10.0K
This lesson defines the leveling effect in acidic and basic solutions and its role in aqueous and non-aqueous solutions. It is essential to understand the competing nature of various species in a chemical system.
The Leveling Effect of a Solvent
A generic acid (HA) reacts with the generic base (B-) to yield the corresponding conjugate base (A-) and conjugate acid (HB):
10.0K
Solubility03:00

Solubility

21.9K
Solution, Solubility, and Solubility Equilibrium
A solution is a homogeneous mixture composed of a solvent, the major component, and a solute, the minor component. The physical state of a solution—solid, liquid, or gas—is typically the same as that of the solvent. Solute concentrations are often described with qualitative terms such as dilute (of relatively low concentration) and concentrated (of relatively high concentration).
In a solution, the solute particles (molecules,...
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Molecular Shape and Polarity03:37

Molecular Shape and Polarity

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Dipole Moment of a Molecule
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Separation of Aldehydes and Reactive Ketones from Mixtures Using a Bisulfite Extraction Protocol
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Separation of Aldehydes and Reactive Ketones from Mixtures Using a Bisulfite Extraction Protocol

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Aryne Compatible Solvents are not Always Innocent.

Sung-Eun Suh1, David M Chenoweth1

  • 1Department of Chemistry, University of Pennsylvania , 231 South 34th Street, Philadelphia, Pennsylvania 19104, United States.

Organic Letters
|August 4, 2016
PubMed
Summary
This summary is machine-generated.

Arynes are reactive intermediates in chemical reactions. This study shows that common solvents like acetonitrile and dichloromethane can participate in aryne-based reactions, contrary to common assumptions.

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Area of Science:

  • Organic Chemistry
  • Reaction Mechanisms

Background:

  • Arynes are crucial intermediates in organic synthesis.
  • Solvents like acetonitrile and dichloromethane are typically considered inert in aryne chemistry.
  • The reactivity of arynes can lead to unexpected side reactions.

Purpose of the Study:

  • To investigate the role of common solvents in aryne-based reactions.
  • To explore potential solvent participation in aryne transformations.
  • To provide mechanistic insights into the triple aryne-tetrazine reaction.

Main Methods:

  • Mechanistic investigation of aryne-based reactions.
  • Analysis of reactions involving arynes in acetonitrile and dichloromethane.

Main Results:

  • Acetonitrile and dichloromethane are not always inert solvents in aryne chemistry.
  • Evidence of solvent participation in aryne-based reactions was observed.
  • Side reactions involving solvent participation were identified.

Conclusions:

  • Commonly used solvents can actively participate in aryne transformations.
  • The assumption of solvent inertness in aryne chemistry needs re-evaluation.
  • Understanding solvent participation is key for controlling aryne reaction outcomes.