Chapter 21 Phenols
Chapter 21 Phenols
Chapter 21 Phenols
Chapter 21:
Phenols and Aryl Halides–
Nucleophilic Aromatic Substitution
1
Phenols and Aryl Halides
Cl CH3
NO2
OH OH
OH
OH OH OH
OH
OH
OH
1,2-Benzenediol 1,3-Benzenediol 1,4-Benzenediol
(catechol) (resorcinol) (hydroquinone)
Arenediazonium salt
Question:
If you are given three unknown samples: one is benzoic acid;
one is phenol; and one is cyclohexyl alcohol; how would you
distinguish them by simple chemical tests?
Recall acidity of
H H
O O O
H
O
> >
O O
H + Na OH + H2O
R O R O Na
(soluble in water)
O O Na
H
+ NaOH
(soluble in water)
O
H
+ NaOH No Reaction
(immiscible
with H2O)
CCB1013 Organic Chemistry 13
Reactions of Phenols as Acids
O O
H
O O Na
+ NaHCO3
+ CO2(g) + H2O
(gas evolved)
O
H
+ NaHCO3 No Reaction
O
H
+ NaHCO3 No Reaction
O O
Carboxylic acid anhydride
R O R
base
OH O R
Phenol O
Acid chloride Ester
R Cl
base
Br2
o
+ HBr
CS2, 5 C
Monobromination can be carried out
using carbon disulfide at low T to
reduce electrophilic reactivity of Br2 Br
OH OH OH
NO2
20% HNO3
+
o
25 C
NO2
(30-40%) (15%)
OH
conc. H2SO4
100oC
SO3H
CCB1013 Organic Chemistry 19
END OF CHAPTER 21