Haloalkaes Flashcards
(22 cards)
What are halo alkanes
Compounds containing carbon, hydrogen and at least one halogen atom
Primary halolkanes
One carbon attatched to the carbon adjoining the halogen
Secondary halo alkane
2 carbons attatched to carbon atom adjoining the halogen
Tertiary halolkanes
3 carbons attatched to the carbon atom ajoining the halogen
Carbon - halogen polar bond in halolkanes
Halogens are (generally) more electronegative than carbon - so POLAR The polar positive carbon is electron dificient - can be attatcked by a nucleophile
Neucelophiles
Elecron pair donators
OH- , CN- and NH3 are all
React with halolkanes
Water - nucleophile but reacts SLOWLY
Hydrolysis
Involves water or an aqueous solution of a hydroxide
Reagent = OH-( e.g. NaOH)
Heat under reflux
Halo alkane — alcohol
What happens in hydrolysis of halo alkanes - nucleophilic substitution
Nucleophile approaches carbon (attatched to halogen)on OPPOSITE side
Direction of OH- ion minimises repulsion between nuc and slightly negative halogen
A lone pair of electrons on OH- ion donated to slightly positive carbon
Bond between oxygen of OH- and Carbon atom
The carbon- halogen bond breaks by HETEROLYTIC fission
Halide ion and alcohol produced
Water as nucleophile for hydrolysis ?
Slower reaction
Produces H+ ion too
Strength of carbon- halogen bond in halolkanes
Weaker bond = faster reaction
As the bonding electrons get further from nucleus - more shielding- bond enthalpies LOWER
Iodoalkanes react faster than bro alkanes
Testing strength of carbon halogen bond with silver nitrate ions
Ag+ + X- —- AgX
The silver ions react with halide ions ONCE THEY form , giving a silver halide precipitate
Faster precipitate = faster substitution reaction = more reactive halo alone
AgI precipitate
Chlorofluorocarbons
Halo alkanes
Chlorine, fluorine and carbon
Stable, volatile, non flammable , non toxic
What is the ozone layer
Outer edge of atmosphere- 10-40km from earths surface
O3
Absorbs UV Ray’s from sun
Formed naturally, when an oxygen is broken down into 2 free radicals by UV
Ozone formation
O2 +UV—– O+O
O2+O— O3
Ozone depletion equation
O3+ UV– O2+ O
Destruction of the ozone layer
Holes forming
CFC’s in atmosphere absorb UV and split to form chlorine free radicals
Free radicals catalyse destruction of ozone- destroy ozone molecule adn then regenerated to destroy more ozone
Step 1 of destruction of ozone layer with CFCS
Chlorine free radicals produced
Photo dissociation
Homolytic fission
UV provides sufficient energy to break bonds
How do you work out in CFC’s which forms free radicals
Whichever bond has the lowest enthalpy - so it breaks
Step 2 of ozone layer destruction ( with chlorine radicals)
These radicals are catalysts - react with ozone to form an intermediate( e.g. Cl0dot) and an O2 molecule
PROPAGATION
CL DOT + o3— o2 + Clo dot
Cl0dot + O (breakdown of oxygen from UV) — o2 + cl2
Overall reaction f destruction of ozone by CFC
O3+O— 2O2
Nitrogen oxide - destroying ozone
NO’ free radicals from nitrogen oxides can destroy ozone too, Nitrogen oxides are produce by car + air craft engines and thunderstorms
R+ O3– RO + o2
RO+ o– R+ o2
Alternatives to CFC’S
HCFC’s — breaks down ozone
HFC’s— no chlorine
ALTERNATIVES,green house gases