addition reactions of alkenes Flashcards
addition reaction
a reaction where two molecules react together to produce one
e.g C2H4 + H2 = C2H6
reaction of alkenes with hydrogen
change in functional group: alkene –> alkane
reagent: hydrogen
conditions: nickel catalyst
type of reaction: addition/reduction
electrophile
an electron pair acceptor
electrophillic addition: reactions of alkenes
a pi bond is weaker than a sigma bond so less energy needed to break the pi bond. the pi bonds in alkenes are areas with high electron density. this is more accessible to electrophillic attack by electrophiles. alkenes undergo addition reactions.
reaction of alkenes with a dihalogenoalkane
change in functional group: alkene –> dihalogenoalkane
reagent: halogen (bromine)
conditions: room temperature
mechanism: electrophillic addition
type of reagent: electrophile, halogen δ+ (Br δ+)
type of bond fission: heterolytic
what happens as a Br2 molecule approaches an alkene?
the pi bond electrons repel the elctron pair in the Br-Br bond. this induces a dipole. Br2 becomes polar and electrophillic (Br δ+).
carbocation
positive charge on a carbon atom
reaction of alkenes with a halogenoalkane
change in functional group: alkene –> halogenoalkane
reagent: halogen halide (HCl or HBr)
conditions: room temperature
mechanism: electrophillic addition
type of reagent: electrophile, H δ+
type of bond fission: heterolytic
why is HBr a polar molecule?
Br is more electronegative than H. H δ+ is attracted to the electron-rich pi bond.
what if the alkene is unsymmetrical?
addition of hydrogen bromide can lead to two isomeric products
e.g. but-1-ene will form a mixture of 1-bromobutane and 2-bromobutane
in electrophillic addition to alkenes where is the major product formed?
via the most stable carbocation intermediate
what is the order of stability for the carbocations?
tertiary < secondary < primary
what makes a carbocation stable?
the methyl groups on either side of the positive carbon are electron releasing and reduce the charge on the ion which stablises it
diol mechanism
reagent: KMnO4 in an acidified solution
conditions: room temperature
type of reaction: oxidation
observation: purple colour of MnO4- ion will decolourise to colourless
reaction of bromine water with alkenes
reagent: bromine dissolved in water (BrOH)
conditions: room temperature
type of reaction: addition
observation: orange colour of bromine water will decolourise to colourless
hydration of alkenes to form alcohols
CH2CH2 (g) + H2O (l) = CH3CH2OH (l)
essentional condition for hydration of alkenes to form alcohols
high temperature - 300 - 600 degrees Celsius
high pressure - 70 atm
catalyst of concentrated H3PO4
hydration reaction
a reaction where water is added to a molecule
polyalkenes
unreactive due to strong C-C and C-H bonds
polyethene use
used to make plastic bags, buckets, bottles.
it is a flexible, easily moulded, waterproof, chemical proof and low density plastic
polypropene use
stiffer polymer, used in utensils and containers and fibres in rope and carpets
methods of disposal of waste polymers
incineration
recycling
feedstock for cracking
incineration
rubbish is burnt and energy produced is used to generate electricity.
some toxins can be released on incineration, e.g. combustion of halogenated plastics can lead to formation of toxic, acidic waste products such as HCl.
modern incinerators burn more efficiently and most toxins and pollutants can be removed.
greenhouse gases still emitted
volume of rubbish greatly reduced
recycling
saves raw materials - nearly all polymers are formed from compounds sourced/produced from crude oil. saves precious resources.
polymers need collecting/sorting - expensive process in terms of energy and manpower. polymers can only be recycled into the same type - so careful separation needs to be done.
thermoplastic polymers can be melted down and reshaped
feedstock for cracking
polymers can be cracked into small molecules which can be used to make other chemicals and new polymers - saves raw materials
biodegradeable polymers
can be made from substances like maize and starch