Antiseptics and disinfectants chlorophenols

C6H10 + Br2 > C6H10Br2 (1, 2dibromocyclohexane) Orange bromine colour disappears and a white precipitate of 2, 4, 6Tribromophenol is formed

Surfactants and detergents - alkyl phenols

Preparation of pharmaceuticalssalicylic acid

Delocalised pi e's (lower e' density) in benzene, halogen cannot be polarised sufficiently.. Catalyst needed!

Localised e's in alkenes (high electron density) so can polarise bromine

Retains delocalisation and stability

Delocalised structure - p orbitals overlap sideways forming a pi e- cloud of e- density above and below plane of carbons

Under normal conditions: no decolourising bromine h2o, reacting with strong acids, reacting with Cl, Br or I

Epoxy resins for paints bisphenol

Uses

C6H5OH + 3Br2 aq. > C6H2OHBR3 + 3HBr

2C6H5OH + 2Na > 2C6H5ONa+ + H2

Phenol Forming salts

Slightly soluble in water however less soluble in water than alcohols

Lone pair of e's on oxygen drawn into the ring - higher e' density in the ring - ring is activated. higher e' density polarises Br

Reactivity compared with alkenes and phenols

Does not take part in addition reaction like alkenes but substitution

Molecular Formula: C6H6

Benzene
Halogenation Nitration
Formation of Cl+: AlCl3 + Cl2 > AlCl4- + Cl+ Kekule structure is wrong

C-C bond lengths the same

Low reactivity die to delocalised ring of electrons

Lower enthalpy change (-208kj mol-1)

C6H6 + Cl2 > C6H5Cl + HCl

Formation of NO2+ (electrophile): HNO3 conc. + H2SO4 conc. > H20 + HSO4- + NO2+

Dissolved in water - forms a weak acidic solution - loses H+ from OH group

C6H6 + HNO3(conc.) > C6H5NO2 +NO2

C6H5OH + aq < > C6H50- + H+

Regeneration of AlCl3: AlCl4- + H+ > AlCl3 + HCl

Catalyst NEEDED, halogen carrier e.g. FeBr3, AlCl3, Fe

Regeneration of H2SO4: HSO4- + H + > H2S04

Conditions: 50'C . Catalyst: H2S04 conc.

C6H5OH + NaOH > C6H5ONa+ + H2O

Neutralised by NaOH aq > Sodium phenoxide and water