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Reactions of Alkenes

The most common reactions of alkenes are addition reactions. In these reactions, the C=C double bond is broken and converted into a C-C single bond. To satisfy the requirement of four-coordinate carbon centers, each carbon atom gains a new single bond. When unsymmetrical reagents (HBr, H-OH, etc.) are added to alkenes, two possible products can often be obtained. Markovnikov's rule (see the relevant mechanisms) can often be used to predict the major product. The following table summarizes most of the important reactions covered in this class.

Select one of the following options
The table of reactions shown below can display either a generic alkene,
a specific chain (2-methyl-1-propene) or a cyclic compound (1-methylcyclohexene).

Generic

Chain

Ring

Type Reaction Stereochem.
Hydrogenation
ALKENE.GIF (565 bytes) A_H2.GIF (646 bytes) ALKANE.GIF (793 bytes)
syn
Halogenation
(X = Cl, Br)
ALKENE.GIF (565 bytes) A_X2.GIF (427 bytes) DIHALIDE.GIF (809 bytes)
anti
Halohydrin
formation
(X = Cl, Br)
ALKENE.GIF (565 bytes) A_X2H2O.GIF (488 bytes) HALOHYDR.GIF (831 bytes)
anti
Hydrohalogenation
(X = Cl, Br, I)
ALKENE.GIF (565 bytes) A_HX.GIF (427 bytes) HALIDE.GIF (807 bytes)
 
Addition of HBr
(with radicals)
ALKENE.GIF (565 bytes) A_HBR.GIF (607 bytes) BROMIDE.GIF (818 bytes)
 
Hydration
ALKENE.GIF (565 bytes) A_H2O.GIF (619 bytes) ALCOHOL.GIF (833 bytes)
ALKENE.GIF (565 bytes) A_H2OHG.GIF (814 bytes) ALCOHOL.GIF (833 bytes)
ALKENE.GIF (565 bytes) A_H2OBH3.GIF (817 bytes) ALCOHOL.GIF (833 bytes)
 
Cyclopropane
via carbenes
ALKENE.GIF (565 bytes) A_CHCL3.GIF (594 bytes) CYCLOCCL.GIF (936 bytes)
ALKENE.GIF (565 bytes) A_CH2I2.GIF CYCLOPRO.GIF (920 bytes)
 
Hydroxylation
ALKENE.GIF (565 bytes) A_OSO4.GIF (724 bytes) DIOL.GIF (835 bytes)
syn
Diol
Cleavage

DIOL.GIF (835 bytes) A_HIO4.GIF (590 bytes) CARBONYL.GIF (866 bytes)
 
Oxidative
Cleavage
ALKENE.GIF (565 bytes) A_OZONE.GIF (661 bytes) CARBONYL.GIF (866 bytes)
ALKENE.GIF (565 bytes) A_KMNO4.GIF (630 bytes) CARBONYL.GIF (866 bytes)
 

This page was last modified on October 5, 2005
and was written and is maintained by Clarke Earley
Kent State University Stark Campus
Department of Chemistry
email: cearley@stark.kent.edu
Copyright © 2000 Clarke Earley, Kent State University. See also the Fair Use Statement.