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Chapter 9

Alcynes

Chapter 9

Alkynes

Structure and Physical Properties of Alkynes
Introduction: In nature, compounds containing both carbon and hydrogen are known as "hydrocarbons". Aliphatic hydrocarbons are compounds whose …
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 …
Acidity of 1-Alkynes
The acidic strength of hydrocarbons follows the order: Alkynes > Alkenes > Alkanes. The strength of an acid is commonly expressed in units of pKa …
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 …
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 …
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 …
Electrophilic Addition to Alkynes: Hydrohalogenation
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 …
Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration
Introduction Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of …
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
Introduction One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is …
Alkynes to Carboxylic Acids: Oxidative Cleavage
Alkynes undergo oxidative cleavage in the presence of oxidizing reagents like potassium permanganate and ozone. The triple bond — one σ bond …
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 …
Reduction of Alkynes to trans-Alkenes: Sodium in Liquid Ammonia
Alkynes can be reduced to trans-alkenes using sodium or lithium in liquid ammonia. The reaction, known as dissolving metal reduction, proceeds with an …
Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Ynones are a valuable functional group and building block in organic synthesis. Ynones serve as a precursor to many important organic functional groups …
Synthesis of Wavelength-shifting DNA Hybridization Probes by Using Photostable Cyanine Dyes
In this protocol, we demonstrate a method for the synthesis of 2'-alkyne modified deoxyribonucleic acid (DNA) strands by automated solid phase …
Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
We present the chemoselective synthesis of 1-(iodoethynyl)-4-methylbenzene, 1-(1,2-diiodovinyl)-4-methylbenzene, and …