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Related Concept Videos

Alkyl Halides02:45

Alkyl Halides

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...
Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
Structure and Nomenclature of Thiols and Sulfides02:17

Structure and Nomenclature of Thiols and Sulfides

Thiols and sulfides are sulfur analogs of alcohols and ethers, respectively, where the sulfur atom takes the place of the oxygen atom. Thus, thiols are generally represented as RSH, where R is an alkyl substituent and —SH is the functional group. On the other hand, in sulfides, the central sulfur atom is bonded to two hydrocarbon groups on either side. Depending upon the type of group, sulfides can be either symmetrical or asymmetrical. Both thiols and sulfides display a bent geometry, similar...
Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...

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Related Experiment Video

Updated: Jun 19, 2026

Synthesis and Characterization of 1,2-Dithiolane Modified Self-Assembling Peptides
09:54

Synthesis and Characterization of 1,2-Dithiolane Modified Self-Assembling Peptides

Published on: August 20, 2018

Long-chain alkylthiol assemblies containing buried in-plane stabilizing architectures.

Hung-Hsun Lee1, Zivile Ruzele, Lyuba Malysheva

  • 1Division of Molecular Physics, Department of Physics, Chemistry and Biology, Linköping University, 58183 Linköping, Sweden.

Langmuir : the ACS Journal of Surfaces and Colloids
|October 2, 2009
PubMed
Summary

Researchers created complex self-assembled monolayers (SAMs) using novel alkylthiol compounds. These engineered nanoscopic architectures, stabilized by hydrogen bonds, offer a robust platform for advanced applications.

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Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation
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Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
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Last Updated: Jun 19, 2026

Synthesis and Characterization of 1,2-Dithiolane Modified Self-Assembling Peptides
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Published on: August 20, 2018

Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation
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Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
12:30

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework

Published on: April 9, 2018

Area of Science:

  • Materials Science
  • Surface Chemistry
  • Nanotechnology

Background:

  • Self-assembled monolayers (SAMs) are crucial for surface engineering.
  • Existing alkyl SAMs provide a foundation for more complex structures.
  • Controlling molecular architecture in SAMs is key for advanced applications.

Purpose of the Study:

  • To synthesize and characterize novel alkylthiol compounds for complex SAMs.
  • To investigate the formation, structure, and stability of these SAMs.
  • To explore the role of hydrogen bonding in SAM structural integrity.

Main Methods:

  • Synthesis and structural confirmation (NMR, elemental analysis) of alkylthiol compounds.
  • Characterization of SAMs on gold using contact angle goniometry, ellipsometry, cyclic voltammetry, and IR reflection absorption spectroscopy.
  • Computational modeling (DFT) to analyze infrared spectra and molecular orientation.

Main Results:

  • Highly ordered, methyl-terminated SAMs were successfully formed from diluted solutions.
  • Hydrogen bonding networks between amide groups stabilize the SAM structure.
  • Deuterated compounds aided in resolving the packing, conformation, and orientation of internal modules.

Conclusions:

  • The synthesized compounds form robust SAMs with tunable nanoscopic architectures.
  • Hydrogen bonding plays a critical role in stabilizing the complex SAM structure.
  • This extended SAM platform enables precise nanoscale engineering for applications like cell membrane mimetics and molecular nanolithography.