Haloalkanes Flashcards
Define nucleophile
Electron pair donor
Why are halogenoalkanes reactive
Halogens are more electronegative than carbon creating a polar bond
This means nucleophiles can attack the bond
Nucleophile examples (3)
Ammonia
Hydroxide ions
Cyanide ions
Halogenoalkanes reacting with hydroxide ions conditions and overall reaction to form alcohols
Warm aqueous sodium hydroxide
Reflux
R-X + NaOH -> ROH + NaX
Halogenoalkanes reacting with cyanide ions conditions and overall reaction to form nitriles
Warm ethanolic Potassium cyanide
Reflux
R-X + KCN -> RCN + KX
Halogenoalkanes reacting with ammonia conditions and other products when amines are formed
Heat with ethanolic ammonia
Excess ammonia
Produced an amine and an ammonium ion with the halogen ion
Halogenoalkanes become more or less reactive down the group?
More
What determines reactivity of halogenoalkanes?
Bond enthalpy, not bond polarity
Bond with the lowest enthalpy is the easiest bond to break
Halogenoalkanes reacting with hydroxide ions conditions and overall reaction to form alkenes
Warm ethanolic sodium hydroxide
Reflux
CH3CHXCH3 + KOH -> CH2CHCH3 + H2O + KX
How to know if substitution or elimination reaction will occur
Substitution to make an alcohol if water is the solvent
Elimination to make an alkene if ethanol is the solvent
What is a CFC?
Chlorofluorocarbons
Stable molecules (until broken down by UV) that have had all their hydrogens replaced by chlorine and fluorine
Why are C-Cl bonds broken easiest by UV in CFCs
They have the lowest bond enthalpy
CFC and ozone free radical substitution mechanism, overall equation and what is the catalyst?
I: CCL3F -UV> •CCl2F + •Cl
P: •Cl + O3 -> ClO• + O2
ClO• + O3 -> •Cl + 2O2
T: 2•Cl -> Cl2
Overall: 2O3 -> 3O2
Catalyst: •Cl
How did we use CFCs?
They were used in fridges as refrigerant and propellants in deodorants
Why did we stop using CFCs, what do we use now and why?
It was damaging the ozone layer and risks outweighed benefits
Ozone absorbs most harmful UV radiation that causes skin cancer
Now: HFCs are used (hydrofluorocarbons) as they don’t have chlorine in them