25.3 the chemistry of phenol Flashcards
draw phenol
page 442
draw 2-hydroxybenzoic acid
page 442
draw 2-nitrophenol
page 442
draw 2-phenylethanol
page 442
draw phenoxide ion
page 443
why is phenol less soluble in water than alcohol?
phenol has a non- polar benzene ring
what is formed when phenol is dissolved in water?
phenoxide ion and proton
why can phenol act as a weak acid?
ability to dissociate to produce a proton
what can be used to distinguish between a phenol and a carboxylic acid?
- sodium carbonate
- carboxylic acids reacts, phenols don’t
what happens to the Ka values as the acidity increases?
Ka increases
write the reaction between phenol and sodium hydroxide
page 443
what conditions and reagents are used in the electrophilic substitution of the bromination of phenol?
Br2
what conditions and reagents are used in the electrophilic substitution of the nitration of phenol?
HNO3
explain the relative resistance to bromination of benzene compared to phenol and cyclohexene
- benzene pi-bonds are delocalised
- phenol a lone pair of electrons on the oxygen or the OH group is (partially) delocalised into the ring
- cyclohexene electrons are localised
- benzene has a lower electron density
- phenol has a higher electron density
- cyclohexene has a higher electron density
- benzene cannot polarise or induce a dipole in Br2 - - phenol can polarise the Br2 OR cyclohexene can polarise Br2 or the Br–Br bond
explain the relative resistance to bromination of benzene compared to phenol and cyclohexene
- benzene pi-bonds are delocalised
- phenol a lone pair of electrons on the oxygen or the OH group is (partially) delocalised into the ring
- cyclohexene electrons are localised
- benzene has a lower electron density
- phenol has a higher electron density
- cyclohexene has a higher electron density
- benzene cannot polarise or induce a dipole in Br2
- phenol can polarise the Br2
- cyclohexene can polarise Br2 or the Br–Br bond
