C15 - Haloalkanes Flashcards
What is a haloalkane?
Compounds containing carbon, hydrogen and at least one halogen
How do you name haloalkanes?
1) Prefix added to longest carbon chain
2) Numbered
3) If more than one haloalkane present, then listed in alphabetical order
What can haloalkanes be classified as?
Primary - carbon attached to 1 alkyl group
Secondary - carbon attached to 2 alkyl groups
Tertiary - carbon attached to 3 alkyl groupss
Why is the carbon-halogen bond polar?
Halogen atoms are more electronegative than carbon atoms
Electron pair closed to halogen atom
Therefore, bond is polar
What’s a nucleophile?
Electron pair donor
Examples of nucleophiles
-Hydroxide ions: OH-
-Water molecules: H2O
-Ammonia molecules: NH3
What is nucleophilic substitution?
Reaction where a nucleophile is attracted to an electron-deficient carbon atom, replacing an atom/group of atoms on the carbon atom
What’s hydrolysis?
Reaction with water that breaks a chemical compound into two compounds
H+ and OH- become incorporated into the two compounds
What mechanism is responsible for the hydrolysis?
Nucleophilic substitution
What happens during the hydrolysis of a haloalkane?
1) Nucleophile, OH-, approaches C atom attached to halogen, from opposite side to halogen
2) Direction of attack by OH- minimises repulsion between nucleophile and delta+ carbon atom
3) Lone pair of e- on OH- is attracted and donated to delta+ carbon atom
4) New bond formed between O atom of OH- and C atom
5) Carbon-Halogen bond breaks by heterolytic fission
6) New organic product is alcohol, halide ion also formed
Hydrolysis of haloalkanes conditions and products
Haloalkane + NaOH (aq) —> Alcohol + sodium halide
Heat and reflux
What happens to carbon-halogen bond strengths down the group?
They decrease
Why happens to reactivity of haloalkanes down the group
Increase
How do you measure the rate of hydrolysis?
Hydrolysis of haloalkanes with water
Carry out reaction in the presence of aq silver nitrate and ethanol solvent
Halide ions exact with silver ions to form precipitate of silver halide
Record time taken for precipitate to form
What happens to the rate of hydrolysis down the group?
Increases