Alkenes Flashcards
Describe the structure and bonding in alkenes
Structure: trigonal planar , 120°
Bonding : double carbon bond (pi and sigma)
Explain what a pi bond is
Side to side overlap of p orbitals in plane above and below sigma bond
Electron rich centre
State the general formula of alkenes
CnH2n
Why might the formula of an alkene not fit the general formula?
Diene or cyclic
Define stereoisomerism
Same structural formula but different orientation in space
Why does stereoisomerism not arise in alkanes?
Don’t have pi bond which restricts rotation
What must a compound have to display stereoisomerism?
Double carbon bond
Two different groups attached to each carbon atom involved in double bond
Give the types of E/Z isomerism
E= trans (H on opposite sides of c=c)
Z= cis (H on same side of c=c)
How do you determine if a compound has E/Z(cis/trans) isomerism?
Has c=c
Has two different groups on each carbon atom
Highest priority group on opposite sides = E
On Same side= Z
How do you determine if a compound has cis/trans isomerism?
Has one H bonded to each carbon atom
Cis= H on same side
Z=H on opposite sides
How is priority assigned to groups?
Atom with highest atomic number (proton)
If the same do next atom along with highest atomic number
What is the name for the method of assigning priority?
Cahn-ingold-prolog principle
Do E or Z isomers have a higher BP, why?
E
Fit more closely and compact so have more surface contact points so London forces are stronger
Describe and explain the reactivity of alkenes
Fairly reactive
In pi bond e are above and below the plane of the sigma bond so more exposed
Pi have a low bond enthalpy so are easily broken
State the addition reactions possible with alkenes
Hydrogenation
Elecrrophillic addition:
Halogenation
Addition of hydrogen halide
Hydration
Polymerisation
State conditions, products and reagents for hydrogenation
Nickel catalyst
Hydrogen
Alkane
State conditions, products and reagents for hydration
Acid catalyst
Steam (water at high temp)
Mixture of alcohols
Describe the test for alkenes
Add bromine water
Positive= orange to colourless
What is Halogenation?
Electrophillic addition
What is an electrophile?
Species that accepts a pair of electrons
Describe electrophillic addition of Br2
Br2 approaches double bond
Electron rich Centre induces dipole
Pi bond breaks donating 2xe to positively partially charged Br
Br2 breaks via heterolytic fission producing two ions
Br+ bonds to carbon producing intermediate (carbonation)
Br- bonds to carbocation by donating lone pair of electrons to form drive covalent bond
haloakane is formed
Define carbocation
Positively charged carbon
What do curly arrows show?
Movement of e from donator to reciever
At what temperature does electrophillic addition occur at?
Rapid at room temperature