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Background Information for Alkenes, Alkynes, and Dienes

Alkenes, Alkynes, and Dienes

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Nomenclature of Alkenes, Alkynes, and Dienes

Reactions of Alkenes
In Markovnikov addition, H of HZ adds to carbon with most hydrogens directly attached; the more stable carbocation intermediate is formed. In anti addition, the groups add on opposite sides of the double bond. In syn addition, the groups add on the same side of the double bond. A regioselective reaction is a reaction in which one of two possible isomers predominates. A regiospecific reaction is a reaction in which one of two possible isomers is formed exclusively. An hydrogen halide adds across a double bond to form an alkyl halide, via Markovnikov addition. Halogen adds across a double bond to form a dihalolalkane, with anti addition. Water adds across a double bond to produce an alcohol, via Markovnikov addition. Hydrogen adds across a double bond, via syn addition, to form an alkane.

This reaction can be used to determine the position of a double bond in an unknown alkene.

Related to the Wittig reaction is the . This uses a less accessible silicon-based reagent in place of the phosphorane, but it allows for the selection of E or Z products. If an E-product is desired, another alternative is the , which uses the carbanion generated from a . The based on an organochromium intermediate also delivers E-products. A titanium compound, , is useful for the synthesis of methylene compounds; in this case, even esters and amides react.

Oxidation of Alkenes and Alkynes

In the , a  derivative is prepared from a diene and a reactive or electron-deficient alkene.

Oxidation Reactions of Alkenes and Alkynes
Potassium permanganate oxidizes alkenes to diols, with syn addition. Ozone oxidizes alkenes to aldehydes and / or ketones. Potassium permanganate oxidizes alkenes to diketones. Ozone oxidizes alkynes to carboxylic acids.

Another important method for alkene synthesis involves construction of a new carbon-carbon double bond by coupling of a carbonyl compound (such as an or ) to a equivalent. Such reactions are sometimes called olefinations. The most well-known of these methods is the , but other related methods are known.

Properties, Synthesis and Reactions of Alkenes and …

Organic chemistry: “Synthesis using addition to alkenes”. Some synthesis problems involving alkenes and  addition.

Organic chemistry: “ synthesis and reactions”. of carbons; acidity of alkynes; use of anions as for SN2 reactions and for attack on (). synthesis from by double elimination; synthesis from alkenes by -double . reactions. Hydrogenation of alkynes; hydrogenation of with catalyst to form alkenes; sequential one-electron reduction of alkynes with sodium metal to form trans alkenes. addition of HX to alkynes; addition of X2 to alkynes (). ; ; mercuric ion-catalyzed hydration of alkynes to form

Organic chemistry: “ of alkenes”. addition reactions. Addition of OsO4 (osmium ) to achieve . Using to achieve anti . A synthesis problem. The synthetic toolbox. When does hindrance block one face of a planar intermediate?

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  • Synthesis and Reactions of Alkenes and ..

    Synthesis of Alkenes

  • Synthesis of Alkenes - [PPT Powerpoint]

    Reactions of Alkenes

  • Alkynes and Alkenes Synthesis | Alkene | Unit Processes

    Organic chemistry: “”. Addition reactions with alkenes: addition of H2 (hydrogenation); addition of HX (). vs. anti-.

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Synthesis of alkynes and alkenes

Organic chemistry: “Alkenes: addition of , BH3, X2”. addition reactions. Addition of H2 (hydrogenation). Addition of , with or without peroxides. Addition of BH3 to get alcohols (-oxidation). Addition of X2.

• Dehydrohalogenation of alkyl halides (c) Dr I.R

Organic chemistry: “Addition to alkenes: H2, HX, H2O”. addition reactions. Addition of H2 (hydrogenation). additions: addition of HX (); addition of H2SO4, H2O (hydration); addition of H2SO4, ROH. Addition of HX in presence of ROOR (radical addition using peroxide initiator). : vs. anti-

Dehydrohalogenation Reactions of Alkyl Halides - …

Organic chemistry: “Ethers”. Ethers. Williamson ether synthesis (preparation of ethers via SN2); . Digression on how to remember the -Lowry and Lewis definitions of acids and bases. Cleavage of ethers with (HX). Effect of positive formal charges on reactivity. Effect of acid or base on reactivity.

of 1-halo-1-alkenes in synthesis ..

Organic chemistry: “Hydrogenation and ”. addition reactions. Problems involving degrees of and hydrogenation (addition of H2). E/Z naming of alkenes. Problems involving addition of X2 (). Forming alkenes from alcohols via E1 (dehydration with H2SO4) or E2.

Synthesis of Alkenes - Towson University

Organic chemistry: “”. How to make and alkyl (). Reactions of and alkyl (with solvents, and , and ). Synthesis problems—using radical , E2, SN2, oxidation (PCC), and for synthesis. The “” technique for solving synthesis problems.

Alkenes: Reactions and Synthesis Flashcards | Quizlet

Organic chemistry: “Introduction to Grignard reagents”. Reaction of Grignard reagents as bases with solvents. Reaction of as with and . Introduction to synthesis with .

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