Saturday, November 13, 2010

CONCEPT MAP 6 ALKENES

Objectives:

describe the chemistry of alkenes as exemplified, where relevant, by the following reactions of ethene: addition of hydrogen, steam, hydrogen halides and halogens oxidation by cold, dilute, acidified manganate(VII) ions to form the diol oxidation by hot, concentrated, acidified manganate(VII) ions leading to the rupture of the carbon-to-carbon double bond in order to determine the position of alkene linkages in larger molecules describe the mechanism of electrophilic addition in alkenes.
BOX 6A: REACTIONS OF ALKENES Carbon-to-carbon double bond broken. Used to determine the position of the double bond in a molecule.

hydrogen halide

Hot, concentrated, acidified KMnO4

Halogenoalkanes
Electrophilic addition

Alkenes

Cold, dilute, acidified KMnO4

Diol
H2

Alkane
Electrophilic addition

halogen

heat, Ni catalyst

Oxidation

dihalogenoalkane
Electrophilic addition

BOX 6B: THE MECHANISM OF ELECTROPHYLIC ADDITION

Consider the addition of bromine to propene.

H H3 C C

H C Br Br H

The + end of the halogen molecule is electrophilic, and can attack the electron rich -bond. Meanwhile, the end of the halogen molecule will accept both of the bond pair of electrons, forming a negative anion.

The electrons in the double bond repel the electrons in the approaching Br2 molecule, causing a dipole.

H H3 C C Br Br C

H H3 C H

H C Br

H C Br H H3 C

H C Br

H C Br H