Define Alkene
Alkenes are unsaturated hydrocarbons containing at least one c=c double carbon bond.
Describe alkene bonding (c=c)
Alkenes contain one double carbon bond which comprises of one π (pi) bond and one σ (sigma) bond. The sigma bond results from the overlap of two orbitals. The pi bond results from the sideways overlap of adjacet p orbitals.
Why are alkene’s C=C bond rigid.
The pi bond prevents rotation about the double bond.
Describe the shape around the double bond and why?
The shape around each carbon atom in the double bond is trigonal planar (120°). Since there are three regions of electron density around each carbon atom (in the C=C bond), the regions repel each other as far as possible .
Define sterioisomers
sterioisomers are compounds with the same structural formula but with different arrangements of atoms in space.
What two conditions must occur for E/Z sterioisomers?
Draw the Z/cis isomer of But-2-ene
CH3 CH3
C = C
H H
Define cis/trans isomers (3)
Draw the E/ trans isomer of But-2-ene
CH3 H
C = C
H CH3
Describe the reactivity of alkenes and why?
Alkenes have a high reactivity due to the π bond formed with the C=C double bond. Unlike the σ bond, the π bonds electrons are outside of the double bond and more exposed, allowing the π bond to easily break and react.
What type of reaction do alkenes commonly undergo?
addition reactions
Describe the process and environment for alkene hydrogenation
Alkene is mixed with hydrogen and passed over a nickel catalyst at 423K, forming an alkane.
Describe the process and environment for alkene halogenation (Cl and Br)
Alkenes react with Chlorine and Bromine at room temperature, to form chloro-/ Bromo- alkanes.
Describe how to test for an unsaturated alkene
Add bromine water drop wise to suspected alkene, bromine water should turn from orange to colourless.
what two alkene addition reactions produce haloalkanes?
Halogenation and reactions with hydrogen halides.
Describe the process and environment for alkene reaction with hydrogen halides
Alkenes react with gaseous hydrogen halides at room temperature to form haloalkanes. Or aqueous concentrated HCl and HBr.
What is formed by the hydration of alkenes?
Alcohols
Describe the process of hydrating alkenes
Alkenes react with steam in the presence of a phosphoric acid catalyst, to form an alcohol. At 300 degrees at 60 atmospheres.
Define electrophile
an electron pair acceptor
What is the mechanism for alkene addition reactions?
electrophilic addition
Describe the process of HBr reacting with an alkene
What does Markownikoff’s rule state?
When a halogen halide reacts with an unsymetrical alkene the hydrogen from the halogen halide attaches itself to the carbon with the most hydrogens (out of the C=C bond).
What increases carbocation stability and why?
The more alkyl groups attached to the positive carbon atom the more stable the carbocation. The alkyl groups push their electrons towards the positive carbon, spreading the positive charge over the alkyl groups making the carbocation more stable.
Describe polymers
Large molecules formed from many small repeat units called monomers.