What is the mechanism for the nucleophilic substitution of a halogenoalkane?

A halogenoalkane is a saturated hydrocarbon chain with a halogen atom (F, Cl, Br or I) attached to a carbon instead of a hydrogen. Halogens have a greater electronegativity than carbon. This means they draw the shared electron pair towards them, which polarises the carbon-halogen bond, and gives the carbon a slight delta positive charge. A nucleophile is a species with a lone pair of electrons. It is attracted to the slightly positive carbon, and donates its lone pair of elections to the carbon to form a bond. This pushes the electrons from the C-halogen bond to the halogen (remember carbon can only have 8 electrons in its valence shell), so that the halogen leaves the carbon compound as a negative halide ion. 

CS

Related Chemistry A Level answers

All answers ▸

How do I calculate rate coefficient units?


Use the concept of electronegativity to justify why the acid strengths of ethanedioic acid and ethanoic acid are different.


explain why the electronegativity of fluorine is greater than that chlorine


Give and explain 2 of the anomalous properties of ice caused by hydrogen bonding (3)