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Lecture# Phenol
Lecture# Phenol
Phenols are compounds with an OH group attached to an aromatic carbon. Although they share the same functional group with alcohols, where the OH group is attached to an aliphatic carbon, the chemistry of phenols is very different from that of alcohols.
Nomenclature.
Phenols are usually named as substituted phenols. The methylphenols are given the special name, cresols. Some other phenols are named as hydroxy compounds.
OH OH CH3 OH Br phenol m-bromophenol OH OH OH OH catechol resorcinol hydroquinone OH p-hydroxybenzoic acid o-cresol OH salicylic acid COOH OH COOH
OH
SO3 Na
NaOH,H2O 300o
H+
OH
phenols, reactions:
1. as acids 2. ester formation
3. ether formation
4. EAS a) nitration b) sulfonation c) halogenation f) nitrosation g) coupling with diaz. salts h) Kolbe
d) Friedel-Crafts alkylation
e) Friedel-Crafts acylation
i) Reimer-Tiemann
with bases:
CH4 < NH3 < HCCH < ROH < H2O < phenols < H2CO3 < RCOOH < HF
OH + NaOH SA SB WB ONa + H2O WA
OH
O COOH
salicyclic acid
aspirin
Because phenols are more acidic than water, it is possible to generate the phenoxide in situ using NaOH.
OH + CH3CH2Br, NaOH CH3 CH3 OCH2CH3
polynitration!
OH
b) halogenation
OH Br2 (aq.) Br
polyhalogenation!
OH Br + Br
OH
c) sulfonation
OH H2SO4, 15-20oC OH SO3H
At low temperature the reaction is non-reversible and the lower Eact orthoproduct is formed (rate control).
At high temperature the reaction is reversible and the more stable paraproduct is formed (kinetic control).
d) Friedel-Crafts alkylation.
OH
e) Friedel-Crafts acylation
OH O + CH3CH2CH2C Cl O AlCl3 OH
AlCl3 OH
f) nitrosation
OH HONO p-nitrosophenol NO OH
OH CH3
NO
O C O
OH COOH
salicylic acid