aromatic chemistry
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evidence to disprove the Kekule model
• benzene does not undergo electrophilic addition • doesn’t decolourise with bromine water • lengths of carbon- carbon bonds are all the same • enthalpy change of hydrogenation is less exothermic than expected • means its more stable
draw ethylbenzene
page 435
draw chlorobenzene
page 435
draw nitrobenzene
page 435
draw phenylethanone
page 435
draw benzoic acid
page 435
draw phenylamine
page 435
draw benzaldehyde
page 435
what is the characteristic mechanism of benzene
electrophilic substitution
what sort of directing group is OH-
2,4- directing group (ortho- and para-)
what sort of directing group is -NH₂
2,4- directing group (ortho- and para-)
draw phenol
page 442
what is another name for 3-bromonitrobenzene?
meta- bromonitrobenzene or m-bromonitrobenzene
comparing the reactivity of phenol and benzene
• lone pair of electrons on OH which is partially delocalised • electron density in the ring increases • more susceptible to attack from electrophiles
position 3 on benzene ring name
meta
position 4 on benzene ring name
para
what are activating groups
2- and 4- directing groups, with exception of the halogens
what are deactivating groups?
3- directing groups