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Alkenes: Reactions

Alkenes represent a chemically rich functional group with many possible transformations. This tutorial looks at a number of typical reactions of alkenes as they appear in a sophomore organic chemistry. The typical reactions of alkenes are:

Catalytic Hydrogenation of Alkenes

–is a reaction between an alkene and hydrogen leading to the formation of alkane or a cycloalkane. Reaction is typically catalyzed by Pt, Pd, or Ni and presents an important reaction for both synthetic chemists and industry.

catalytic hydrogenation of alkenes

Halogenation of Alkenes

–is a reaction between and alkene and halogen leading to the formation of a vicinal dihalide. The reaction is typically only performed with Cl2 or Br2 and is stereospecific (anti-addition).

halogenation of alkenes

Oxyhalogenation of Alkenes

–is a reaction that is very similar to the halogenation of alkenes in both the mechanism and its stereospecificity. The main difference is that the nucleophile in this reaction is water which is taken in a large excess.

oxyhalogenation of alkenes

Alcoxyhalogenation of Alkenes

–is just like the oxyhalogenation reaction but the nucleophile in this reaction is an alcohol. Alcoxyhalogenation is a useful way to make functionalized ethers.

alcoxyhalogenation of alkenes

Hydrohalogenation of Alkenes

–is, perhaps, one of the most “typical” reactions of alkenes that is covered in a lot of details in organic chemistry. In this reaction and alkene reacts with either HCl, HBr, or HI to yield a corresponding alkyl halide.

hydrohalogenation of alkenes

Catalytic Hydration of Alkenes

–is the reaction between an alkene and water catalyzed by a strong acid. It is generally only used with simple molecules due to the possibility of carbocationic rearrangements and harsh conditions.

catalytic hydration of alkenes

Catalytic Addition of Alcohols to Alkenes

–is the reaction that is very similar to the hydration of alkenes. It suffers from the same drawbacks and has a limited usefulness.

catalytic addition of alcohols to alkenes

Radical Hydrohalogenation of Alkenes

–is a very useful reaction that places a halogen on the less substituted carbon of the double bond.

radical hydrohalogenation of alkenes

Oxymercuration-Reduction (Oxymercuration-Demercuration) of Alkenes

–is a reaction that places the hydroxyl (-OH) group on the more substituted carbon of the double bond.  Also, due to the nature of the mechanism of this reactions, no carbocationic rearrangements are observed.

oxymercuration-reduction of alkenes

Alcoxymercuration-Reduction of Alkenes

–is very similar to the oxymercuration-reduction. The reaction produces ethers and is very useful for synthetic chemists.

alcoxymercuration-reduction of alkenes

Hydroboration-Oxidation of Alkenes

–is an extremely useful reaction that results in the hydroxyl group (-OH) onto the less substituted carbon of the double bond. It is also different from many other reactions of electrophilic additions to an alkene is its stereospecificity being one of the few syn addition reactions.

hydroboration-oxidation of alkenes

Epoxidation of Alkenes

–is a fairly common reaction of alkenes that converts the double bond into a three-membered ring with the oxygen atom. This a cyclic functional group is called an epoxide or oxirane.

epoxidation of alkenes

Ozonolysis of Alkenes

–is a reaction that cleaves the double bond oxidizing the carbons to carbonyls or carboxylic acids.

ozonolysis of alkenes

Dihydroxylation of Alkenes

–is one of the more narrowly specialized reactions that selectively converts an alkene into a vicinal diol.

dihydroxylation of alkenes osmium tetroxide

Cyclopropanation of Alkenes

–is one of the few reactions that effectively yields highly strained three-membered rings (cyclopropanes).

cyclopropanation of lakenes

Reactions of Alkenes Combined Spiderweb

reactions of alkenes

 

 


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Drawing and Reading Organic Molecules Structures
  • Molecular Formulas
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Bonding in Organic Chemistry
  • Formal Charges
Nomenclature of Organic Compounds
  • Functional Groups in Organic Chemistry
  • Nomenclature of Alkanes and Cycloalkanes
Acid-Base Chemistry
Stereochemistry
  • Finding Chiral Carbons
Alkenes: Reactions
Alkynes: Reactions
Alcohols: Reactions
Conjugated Systems
  • Synthesis of Dienes
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Reactions Involving Allylic and Benzylic Carbons
  • Radical Substitution in Allylic and Benzylic Position
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Electrophilic Addition to Conjugated Systems: Thermodynamic vs Kinetic Controlled Reactions
Pericyclic Reactions
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Aromatic Compounds: Reactions
Aldehydes and Ketones: Reactions
Carboxylic Acids: Reactions
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