I. Oxidation of alkenes.

Alkenes will oxidize in the presence of oxidizing agents,such as potasium permanganate, cleaving the double bond and adding a hydroxide to each of the carbon atoms that where previously double bonded together and produce a dialcohol.

H

H

H

H

H

H

H

H

H-

|

|

|

=

|

+

KMnO4

+

H2O

[O]

H-

|

|

|

|

H

+

KOH

C-

C-

C

C

C-

C-

C-

C-

|

|

|

|

|

|

|

H

H

H

H

H

OH

OH

+

1-butene

1,2-butanediol

MnO2

 

 

Note: Complete oxidation of alkenes proceeds as follows:

Alkene		Diol/Dialcohol		Aldehyde+ Ketone		Carboxylic Acid
						Carbon Dioxide

 

 

II. Addition of hydrogen.

H

H

H

H

H

H

|

|

|

|

|

|

H-

C-

C

=

C

+

H2

H-

C-

C-

C-

H

|

|

|

|

|

H

H

H

H

H

1-propene

1-propane

 

III. Addition of a halogen (a symmetrical molecule).

H

H

H

H

H

H

H

H

|

|

|

|

|

|

|

|

H-

C-

C-

C

=

C

+

Cl2

H-

C-

C-

C-

C-

H

|

|

|

|

|

|

|

H

H

H

H

H

Cl

Cl

1-butene

1,2-dichlorobutane

 

IV. Addition of an acid (an unsymmetrical molecule).

H

H

H

H

H

H

H

H

|

|

|

|

|

|

|

|

H-

C-

C-

C

=

C

+

HCl

H-

C-

C-

C-

C-

H

|

|

|

|

|

|

|

H

H

H

H

H

Cl

H

1-butene

2-chlorobutane

Note: Markovnikov's Rule states that when an unsymmetrical molecule such as HCl or HOH is added to a carbon-carbon double bond, the hydrogen from the HCl or HOH goes to the double bonded carbon atom that has the larger number of hydrogen atoms attached to it.

 

V. Addition of water( an unsymmetrical molecule).

H

H

H

H

H

H

|

|

|

|

|

|

H-

C-

C

=

C

+

HOH

H-

C-

C-

C-

H

|

|

|

|

|

H

H

H

OH

H

1-propene

2-propanol

(isopropanol)