aromatics and that Flashcards
aliphatic
organic open chains
alicyclic
cyclic structures with aliphatic properties
aromatic
organic compounds with a benzene ring
describe kekule model
planar ring of carbon atoms with alternating single and double bonds. Each carbon is bonded to one hydrogen
describe delocalised model
p orbitals of all six c-c atoms overlap to create pi system- 2 ring shaped clouds of electrons above and below plane. all bonds are the same legnth . electrons are delocalised dont belong to specific caron atom. each carbon is bonded to one hydrogen
evidence for delocalised model
enthalpy of hydrogenation is less exothermic than expected, benzene is more stable than kekule with a stronger resistanve to reaction
x-0raydifffraction shows all bonds to be the same length
first step of bromination of benzene
form an electrophile you need a halogen carrier febr3
2Fe+3Br2=”Febr3
FeBr3 + Br2 = Br+ + FeBr4-
cl halogen carrier
AlCl3
why do halogen carrier help make good electrophiles
accepts lond pair of e from halogen stom on electropphile. lone pair is pulled away, the polarisation in the moeculeincreases froming carbocation
Similarities and differences between the bonding in kekule and delcolised model
Both involve sideways overlap of adjacent p-orbitals. But kekule has alternating pi bonds vs delocalised electrons in pi system
Evidence for kekules model
Bond length
Enthoy change of hydrogenation is less exothermic than expected to reaction
Benzene is less reactive than alkenes. Bromination of benzene requires a catalyst
Relative resistance to bromination of benzene vs phenol csncyclohexene
Cyclohexene has the least resistance then Relative then benzene. In benzene electrons are delocalised into the ring. Cyclohexane electrons are localised between 2 carbon atoms. Benzene cannot polarise br2
How does halogen carrier allow reaction to take place
Introduced permanent dipole on halogen
Binding and structure of benzene
Over lap of p orbitals each orbital donates one electron to delocalised pi system. Electron density above and below plane. It’s a planar ring with equal c c bonds lengths and the bond angle 120