alkenes Flashcards
general formula
CnH2n
what type of hydrocarbons are the alkenes
unsaturated because carbon atoms in c=c do not have the maximum number of hydrogen atom
structure and reactivity:
the C=C double bond contains one sigma and one pi bond
the pi bond forms due to the overlap of p orbitals- this restricts rotation and gives rise to geometric isomerism
why are the alkenes more reactive than alkanes
the C=C bopnd os basically 4 electreons fixed between carbon nuclei, this gives it a high electron density and is attacked by electrophiles
what is an electrophile
an electrophile is a species which seeks out negative centres and accepts a pair of electrons to form a new covalent bond
how does electrophilic addition occur
the pi bond in C=C is weak and takes only small amounts of energy to be broken
- this then allows two new sigma bonds to be formed, the energy released compensates for the breaking of the pi bond
- electrophilic addition is therefore exothermic
examples of electrophilic addition
1) reactions with halogens to form dihaloalkanes
2) hydrogenation to form alkanes
3) hydration to form alcohols
4) reactions with hydrogen halides to form haloalkanes
conditions of each specific reaction
1) with halogens- room temperature + aq solution
2) hydrogen halides- mix in the gas phase
3) with hydrogen- nickel catalyst, 100 degrees
4) with water- phosphoric acid (H3PO4) + 100 C
explaining the electrophilic addition mechanism
1) as a halogen molecule approaches the electron rich C=C bond, it becomes polarised as electrons are repelled away
2) the halogen molecule (electrophile) then becomes polarised as it accepts the electron pair from the weak pi bonds of C=C to form new sigma bonds
3) at the same time, the halogen-halogen bonds also breaks forming a carbocation intermediate
4) lastly the CI reacts with the remaining halide ion to form a new product
markownikoffs rule
when a hydrogen halide reacts with an unsymmetrical alkene, the hydrogen of the hydrogen halide attaches itself the carbon of the alkene
-bearing larger number of hydrogens and smaller number of carbons
addition reactions of unsymmetrical alkenes produce
more than one product
types of carbocations
primary- one carbon chains attached to C+
secondary- two carbon chains attached to C+
tertiary- three carbon chains attached to C+