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Reduction of Alkenes: Catalytic Hydrogenation

Reduction of Alkenes: Catalytic Hydrogenation

Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the...

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...

Preparation of Alkynes: Dehydrohalogenation

Preparation of Alkynes: Dehydrohalogenation

Introduction
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...

Nomenclature of Alkynes

Nomenclature of Alkynes

Alkynes are unsaturated hydrocarbons characterized by the presence of carbon-carbon triple bonds and have a general formula CnH2n-2. The nomenclature of alkynes follows a set of rules similar to alkanes and alkenes; however, alkynes bear the suffix "-yne" instead of "-ane" or "-ene." There are two approaches to naming alkynes:

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Related Experiment Video

Updated: Feb 24, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

Nonacene Generated by On-Surface Dehydrogenation.

Rafal Zuzak¹, Ruth Dorel², Mariusz Krawiec³

¹Centre for Nanometer-Scale Science and Advanced Materials, NANOSAM, Faculty of Physics, Astronomy and Applied Computer Science, Jagiellonian University , Łojasiewicza 11, PL 30-348 Krakow, Poland.

|August 18, 2017

Summary

This summary is machine-generated.

Researchers synthesized nonacene on a surface via dehydrogenation. This allowed detailed analysis of nonacene

Keywords:

atomic force microscopy dehydrogenation hydroacenes nonacene on-surface synthesis scanning tunneling microscopy

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Published on: March 4, 2021

Area of Science:

Surface chemistry
Organic synthesis
Nanotechnology

Background:

Nonacene, a polycyclic aromatic hydrocarbon, presents synthesis and characterization challenges.
On-surface synthesis offers a controlled environment for studying complex organic molecules.

Purpose of the Study:

To achieve on-surface synthesis of nonacene.
To characterize the electronic and structural properties of nonacene and its precursors.
To explore the isomerization pathways during on-surface synthesis.

Main Methods:

On-surface dehydrogenation of a partially saturated precursor using combined scanning tunneling microscopy (STM) and atomic force microscopy (AFM).
On-surface annealing for aromatization.
Scanning tunneling spectroscopy (STS) for electronic property analysis.
Density functional theory (DFT) calculations for orbital mapping and structural validation.

Main Results:

Successful on-surface synthesis of nonacene achieved through dehydrogenation and annealing.
Detailed electronic properties of nonacene molecules on Au(111) characterized using STS.
Spatial mapping of molecular orbitals confirmed by DFT calculations.
Isomerization of intermediate dihydrononacene species observed and characterized.

Conclusions:

On-surface synthesis provides a viable route for creating nonacene.
The study offers in-depth insights into the electronic structure and properties of nonacene.
Thermal dehydrogenation and isomerization are key processes in the on-surface synthesis of polycyclic aromatic hydrocarbons.