Module 4 : Alkenes and Alkynes

Lecture 7 : Alkenes

4.3 Stability of Alkenes

The stability of an alkene depends on its structure. The heat released in a hydrogenation reaction is called the heat of hydrogenation . When an alkene is treated with hydrogen in the presence of a platinum catalyst, hydrogen adds to the double bond, reducing the alkene to an alkane. Hydrogenation is exothermic, evolving about 20 to 30 kcal of heat per mole of hydrogen consumed.

The difference in the stabilities of alkenes is the difference in their heats of hydrogenation. While considering the hydrogenation of 1-butene (a monosubstituted alkene), 2-butene (a disubstituted alkene) and 2-methyl-2-butene (a trisubstituted alkene), 2-methyl-2-butene is more stable by 3.4 kcal/mol and 2-butene is stable by 2.7 kcal/mol (Scheme 1). More substituted double bonds are usually more stable. In other words, the alkyl groups attached to the double bonded carbons stabilize the alkene.

Scheme 1