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Describe phenol
Aromatic compound with OH group attached to benzene ring
How to prepare phenol
R: phenylamine, HNO2
C: temp 10
P: diazonium salt
Then decompose diazonium salt by warming → phenol forms
Structure of phenol
Due to hydrogen bonding:
High mpt bpt
Slightly soluble in water
Why is phenol less soluble compared to alcohol?
Due to presence of benzene ring which strengthens CO bond and weakens OH bond. This makes phenol more acidic
Reaction of phenol with bases
R: NaOH
C: rtp
Reaction of phenol with Na
R: Na
C: rtp
Nitration of phenol
R: diluted/conc HNO3 for mono/tri
C: rtp
Bromination of phenol
R: Br2
C: rtp
Esterification of phenol
R: acyl chloride + NaOH
Why is phenol more acidic compared to alcohol?
Oxygen lone pair delocalises over benzene ring
causing phenoxide ion to stabilise.
Electron density of phenoxide ion increases
so H+ is not strongly attracted to ion.
Therefore more H+ in solution.
What makes alcohol less acidic than phenol?
EDG ethyl group causes O electron density to increase
causing phenoxide ion to combine to H+ more readily.
Therefore fewer H+ in solution.