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Related Concept Videos

Alkyl Halides02:45

Alkyl Halides

21.9K
Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
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Acid Halides to Carboxylic Acids: Hydrolysis01:01

Acid Halides to Carboxylic Acids: Hydrolysis

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Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic...
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SN2 Reaction: Transition State02:26

SN2 Reaction: Transition State

13.0K
An SN2 reaction of an alkyl halide is a single-step process in which bond formation between the nucleophile and the substrate and bond breaking between the substrate and the halide occurs simultaneously through a transition state without forming an intermediate.
When the nucleophile approaches the electrophilic carbon with its lone pairs, the halide acts as a leaving group and moves away with the electron-pair bonded to the carbon. Dotted partial bonds represent the bonds being formed or broken...
13.0K
Predicting Products: Substitution vs. Elimination02:52

Predicting Products: Substitution vs. Elimination

15.1K
When a nucleophile and an alkyl halide react, nucleophilic substitution and β-elimination reactions compete to generate products.
The following factors can influence the mechanisms competing against each other:
15.1K
Electrophilic Addition to Alkynes: Hydrohalogenation02:35

Electrophilic Addition to Alkynes: Hydrohalogenation

12.1K
Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.
12.1K
Predicting Products: SN1 vs. SN202:27

Predicting Products: SN1 vs. SN2

17.7K
Nucleophilic substitution reactions of alkyl halides can proceed via an SN1 or an SN2 mechanism. While in SN2 reactions, the nucleophile attacks the substrate simultaneously as the leaving group departs, in SN1 reactions, the substrate first dissociates to give the carbocation intermediate. Various factors such as the structure of the substrate, the strength of the nucleophile, and the nature of the solvent promote one mechanism over the other.
With increased substitution on the alkyl halide,...
17.7K

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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

Published on: March 24, 2018

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How specific halide adsorption varies hydrophobic interactions.

Philipp Stock1, Melanie Müller1, Thomas Utzig1

  • 1Department for Interface Chemistry and Surface Engineering, Max-Planck-Institut f. Eisenforschung GmbH, Max-Planck-Straße 1, D-40237 Düsseldorf, Germany.

Biointerphases
|January 13, 2016
PubMed
Summary

Specific ion adsorption, particularly iodide, significantly alters hydrophobic interactions (HI) at interfaces. Large halide ions adsorb strongly, influencing surface charge and repulsion, contrary to previous beliefs about hydroxide adsorption.

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Area of Science:

  • Physical Chemistry
  • Surface Science
  • Nanotechnology

Background:

  • Hydrophobic interactions (HI) are fundamental in aqueous systems, driven by water structuring around hydrophobic surfaces.
  • The influence of specific ion adsorption on HI and hydrophobic interfaces is poorly understood and debated.
  • Previous models often assumed intrinsic negative surface charge due to hydroxide adsorption.

Purpose of the Study:

  • To experimentally investigate the effect of specific ion adsorption on forces at hydrophobic interfaces.
  • To elucidate the role of halide ions (iodide, bromide, chloride) and cations (NH4+, Cs+, Na+) in modifying HI.
  • To challenge existing assumptions about surface charging at hydrophobic interfaces.

Main Methods:

  • Atomic force microscopy force spectroscopy at well-defined nanoscopic hydrophobic interfaces.
  • X-ray photoelectron spectroscopy (XPS) for surface analysis.
  • Quartz-crystal-microbalance with dissipation monitoring (QCM-D) to study adsorption.

Main Results:

  • Iodide adsorption dramatically alters the hydrophobic interaction potential, inducing long-range repulsion and subsequent instability.
  • Large halide ions (Br-, I-) adsorb onto hydrophobic self-assembled monolayers (SAMs), with iodide causing SAM disintegration.
  • Cations (NH4+, Cs+, Na+) showed no significant influence on HI.
  • Data contradicts the notion of intrinsic negative surface charge from hydroxide adsorption.

Conclusions:

  • Specific adsorption of large halide ions, especially iodide, is a primary driver of surface charging and altered forces at hydrophobic interfaces.
  • Hydrophobic surfaces interact strongly with specific ions, leading to significant modifications in interfacial forces.
  • The findings necessitate a revision of models describing hydrophobic interactions and surface behavior in electrolyte solutions.