Alcohols And Haloalkanes
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Alcohol properties
Less volatile Higher mp - form h bonds greater solubility due to the polarity of the molecules (decreases as chain gets longer as less of effect on wider molecule)
Classifying alcohols
• Primary alcohol- OH group attached to carbon attached to 2 H and alkyl group • Secondary alcohol- OH group attached to 1 H bond and 2 alkyl groups • Tertiary alcohols - OH group is attached to C w no hydrogen all alkyl
Oxidation of alcohols
Acidified dichromate ions If alcohol oxidised these reduced from orange to green Cr2O7 2- => Cr3+
Oxidation of primary alcohol
+ [O] => aldehyde heat + distil to prevent further reaction +2[O]=> Carboxylic acid heat strong under reflux
Oxidation of secondary alcohols
+ [O] => ketone heat under reflux to ensure fully reacted
Oxidation of tertiary alcohols
Don’t undergo oxidation reactions Acidified dichromate remains orange
Dehydration of alcohols
Heat under reflux with acid catalyst eg conc H2SO4 Product is Alkene Reaction is elimination water is removed
Substitution reactions of alcohols
Nucleophilic React w hydrogen halides form haloalkanes Heat under reflux w sodium halide and sulfuric acid HBr is formed react to form haloalkane
Reactivity of haloalkanes
Carbon halogen bond is polar Carbon ion has a slight positive charge which attracts nucleophiles Nucleophiles replace halogen - nucleophilic sub
Hydrolysis
OH- ion replaces halogen Carbon halogen bond is broken by heterolytic fission Alcohol is formed Use NaOH heated under reflux
Carbon halogen strength
Lower down the group the weaker the carbon halogen bond the more reactive and easier to break down Rate of hydrolysis increases as the strength of the carbon halogen bond decreases
Hydrolysis of primary secondary and tertiary haloalkanes
Tertiary rate is the fastest due to the increased stability of the tertiary carbocation
Organohalogens
Molecules that contain at least one halogen atom joined to carbon chain Rarely found in nature as they aren’t broken down naturally - concern
Ozone layer
Found at outer edge of stratosphere absorb damaging uv radiation Depletion in this leads to damage to species causing more cancer
UV forming ozone
UV breaks O2 down into O radicals O2 molecules react with O radical which forms ozone Rate formed= rate broken down
CFCs
Chlorofluorocarbons very stable due to the strength of carbon halogen bond Stable until reach the stratosphere where they are broken into Cl • which catalyse breakdown of ozone
How do cfcs breakdown ozone
CFCs are broken down via radiation process is photodisociation Forms CF2Cl• + Cl• Propagation 1. Cl• +O3 -> ClO• +O2 2. ClO• + O-> Cl• + O2 O3+O -> 2O2
Other ozone depleting reactions
Nitrogen oxide radicals form during lightning strikes and aircraft travel NO• +O3 -> NO2• + O2 NO2• + O -> NO• + O2 O3+ O -> 2O2