Alkene

Why are alkenes are relatively stable compounds, but are more reactive than alkanes?
Ethylene (ethene), showing the pi bond in green.
According my opinion it is because Alkenes are relatively stable compounds, but are more reactive than alkanes due to the presence of a carbon-carbon pi-bond. It is also attributed to the presence of pi-electrons in the molecule. The majority of the reactions of alkenes involve the rupture of this pi bond, forming new single bonds.

Like single covalent bonds, double bonds can be described in terms of overlapping atomic orbitals, except that, unlike a single bond (which consists of a single sigma bond), a carbon-carbon double bond consists of one sigma bond and one pi bond. This double bond is stronger than a single covalent bond (611 kJ/mol for C=C vs. 347 kJ/mol for C—C)[1] and also shorter with an average bond length of 1.33 Angstroms (133 pm).

Each carbon of the double bond uses its three sp² hybrid orbitals to form sigma bonds to three atoms. The unhybridized 2p atomic orbitals, which lie perpendicular to the plane created by the axes of the three sp² hybrid orbitals, combine to form the pi bond. This bond lies outside the main C—C axis, with half of the bond on one side and half on the other.

Rotation about the carbon-carbon double bond is restricted because it involves breaking the pi bond, which requires a large amount of energy (264 kJ/mol in ethylene). As a consequence, substituted alkenes may exist as one of two isomers, called cis or trans isomers. More complex alkenes may be named using the E-Z notation, used to describe molecules having three or four different substituents (side groups). For example, of the isomers of butene, the two methyl groups of (Z)-but-2-ene (aka cis-2-butene) face the same side of the double bond, and in (E)-but2-ene (aka trans-2-butene) the methyl groups face the opposite side. These two isomers of butene are slightly different in their chemical and physical properties.

It is certainly not impossible to twist a double bond. In fact, a 90° twist requires an energy approximately equal to half the strength of a pi bond. The misalignment of the p orbitals is less than expected because pyramidalization takes place (See: pyramidal alkene). trans-Cyclooctene is a stable strained alkene and the orbital misalignment is only 19° with a dihedral angle of 137° (normal 120°) and a degree of pyramidalization of 18°. This explains the dipole moment of 0.8 D for this compound (cis-isomer 0.4 D) where a value of zero is expected.[3] The trans isomer of cycloheptene is only stable at low temperatures.


As predicted by the VSEPR model of electron pair repulsion, the molecular geometry of alkenes includes bond angles about each carbon in a double bond of about 120°. The angle may vary because of steric strain introduced by nonbonded interactions created by functional groups attached to the carbons of the double bond. For example, the C-C-C bond angle in propylene is 123.9°.


The physical properties of alkenes are comparable with those of alkanes. The physical state depends on molecular mass (gases from ethene to butene - liquids from pentene onwards). The simplest alkenes, ethene, propene and butene are gases. Linear alkenes of approximately five to sixteen carbons are liquids, and higher alkenes are waxy solids.
Alkenes react in many addition reactions, which occur by opening up the double-bond. Most addition reactions to alkenes follow the mechanism of electrophilic addition. Examples of addition reactions are hydrohalogenation, halogenation, halohydrin formation, oxymercuration, hydroboration, dichlorocarbene addition, Simmons-Smith reaction, catalytic hydrogenation, epoxidation, radical polymerization and hydroxylation.
Electrophilic addition

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STUDY PROGRAMME : ISSTE OF CHEMISTRY

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