Related Experiment Video
Updated: May 5, 2026
A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Reaction of NO(2) with selected conjugated alkenes
François Bernard1, Mathieu Cazaunau, Yujing Mu
1Institut de Combustion, Aérothermique, Réactivité et Environnement (ICARE) , CNRS (UPR 3021)/OSUC, 1C Avenue de la Recherche Scientifique, 45071 Orléans Cedex 2, France.
Abstract:
The gas phase reactions of selected alkenes (isoprene, myrcene, ocimene, and 1,3-cyclohexadiene) with NO2 under dark condition have been investigated at T ∼ 298 K and P ∼ 760 Torr of purified air. The kinetic studies were performed under pseudo-first-order conditions using a large excess of NO2 concentration to those of the alkenes. The rate coefficients (in 10(-19) cm(3) molecule(-1) s(-1)) obtained are 1.1 ± 0.2 for isoprene, 2.5 ± 0.3 for myrcene, 8.5 ± 1.2 for ocimene, and 15 ± 1 for 1,3-cyclohexadiene. Several products were identified by using in situ Fourier transform infrared (FT-IR) spectrometry, and acetone was found to be the major product from the reactions of NO2 with myrcene and ocimene, with a formation yield of 22 ± 3% and 26 ± 7%, respectively. The oxidation products from the reactions of NO2 with isoprene and 1,3-cyclohexadiene were found to be mainly nitro compounds identified by FT-IR spectroscopy. Reaction mechanisms were proposed to account for the products observed.
More Related Videos
10:10Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
Published on: July 28, 2018
06:46Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Related Concept Videos
02:24Introduction to Electrophilic Addition Reactions of Alkenes
Addition and elimination...
02:27Preparation of Alkynes: Alkylation Reaction
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.
02:38Electrophilic Addition to Alkynes: Halogenation
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.
02:47Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
01:10α-Alkylation of Ketones via Enolate Ions
02:24Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
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.