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Halogenoalkanes Halogenoalkanes have the general formula CnH2n+1X. X is a halogen.

gen. Can also be primary, secondary and tertiary like alcohols. When naming, the halogen part is named first (prefix chloro-, bromo-, iodo-) followed by name of alkane E.g. CH3Cl = Cloromethane CH3CH2Br = Bromoethane If there is more than one halogen di- and tri- are used to indicate the number of halogens present, e.g. CH 2BrCH2Br = 1,2-dibromoethane

Reactions of Halogenoalkanes: Halogenoalkanes contain polar bonds because the halogen is more electronegative than the carbon. This leaves a carbon with a delta + charge, making it open to attack by nucleophiles. Nucleophiles: attracted to electron deficient atom, d+ and donate a pair of electrons to form a new covalent bond The halogen will be replaced by the nucleophile, which gives a substitution reaction, giving a new functional group.

1. Halogenoalkanes react with aqueous alkalis to form ALCOHOLS

Aqueous hydroxide ions need to substitute the halogen. Sodium hydroxide NaOH(aq) or potassium hydroxide KOH(aq) can be used. The reaction is called hydrolysis and usually carried out under reflux Hydrolysis: is a reaction with water or aq hydroxide ions that break a chemical compound into two compounds

Mechanism:

Water can act as a nucleophile too, but it is a much slower reaction:

First step

Second

step

The overall equation with

water:

If water with dissolved silver nitrate is used, this can tell us about the reactivities of halogenoalkanes When water and an alcohol react, and an alcohol is formed, the silver nitrate will react with the halide ions when they form giving a silver halide precipitate The precipitate that forms first indicates which halogenoalkanes hydrolyses first: Tertiary halogenoalkanes precipitate forms immediately Secondary halogenoalkanes precipitate forms after several seconds

Primary halogenoalkanes precipitate forms after several minutes

This shows that the reactivity is tertiary 3o > secondary 2o > primary 1o

2. Halogenoalkanes react with alcoholic ammonia to form amines

Ammonia NH3 has a lone pair of electrons, and can therefore act as a nucleophile Alcoholic ammonia ammonia dissolved in ethanol. Heated under reflux MECHANISM In the second step, and ammonia molecule removes hydrogen from the NH3 group to form an ammonium ion (NH4+) This can then react with the Br- ion from step 1, to form ammonium bromide: NH4Br

Step 1

Step 2 3. c alkenes

Overall reaction: with ethanol and under reflux Alcoholi alkali to form

When a halogenoalkane reacts with alcoholic alkali, e.g. potassium hydroxide, KOH in hot ethanol, an alkene is made This is an elimination reaction Heated under reflux

Uses of halogenoalkanes: Halogenoalkanes are used as fire retardants and refrigerants Chlorofluorocarbons (CFCs) used to be used in the past because of their unique properties (non-toxic, non-flammable, unreactive), but it was found that they deplete the ozone layer in the atmosphere, so are being phased out (see notes later) Other halogenoalkanes such as hydrofluorocarbons (HFCs) are now used as safer alternatives.