Phenols

Phenol

OH
The antiseptic property
of phenol was discovered
in 1865 by Joseph Lister,
a physician in Scotland.
Listerine, named after him, contains phenol
as the active ingredient.
Today, over two million tons of phenol are
made each year in the US alone.
Phenol is used for resins, glue to make
plywood, plastics, and pharmaceuticals.

Examples of Phenols
OH

OH
OCH3

OH
OCH3

CH(CH3)2
CH3

C
H
O
vanillin

eugenol (cloves; dental

analgesic/antiseptic)
O

CH3O
HO

CH3

CH3

HO

OH

thymol
in thyme)

bisphenol-A
OH

O
C

OCH3

H
capsaicin (hot peppers;
analgesic, anti-inflammatory)

methyl salicylate
(oil of wintergreen)

More phenols
OH

OH
(CH3)3C

OH

OH
C(CH3)3

(CH3)3C

C(CH3)3

C15H29
CH3

urushiol(s)
(poison ivy, oak)

OCH3

BHT
(food preservative)

BHA
(food preservative)
OH

OH
Cl

Cl

Cl

Cl
Cl

pentachlorophenol
(wood preservative)

OH

HO
OH
OH
resveratrol
(antioxidant in red grapes)

CH2CH2CH2CH2CH2CH3
n-hexyl resorcinol (antiseptic)

Slight Acidity of Phenol

Phenol has a Ka = 10-10 (pKa =10)

Alcohols have a Ka = 10-16 (pKa =16)
OH

ROH

RO

The reason phenol is more acidic than an

alcohol is resonance stabilization of the
phenolate anion (next slide)

Resonance of Phenolate ion

O

Substituents that stabilize an anion enhance the acidity of phenol.

Phenol has a pKa = 10; p-nitrophenol has a pKa = 7.1

Picric acid (2,4,6-trinitrophenol)

2,4,6-trinitrophenol is so acidic that it is

called picric acid; it has a Ka = 10-1 (pKa =1)

The enhanced acidity compared to phenol

itself (Ka = 10-10) is due to the increased
resonance stabilization of the conjugate
base (phenolate anion) by the nitro groups:

O
O

IR spectrum of phenol

O-H
C=C

C-O

IR spectrum of cyclohexanol

O-H

C-O

IR spectrum of 1-butanol

O-H
O-H

C-O
C-O

CH3CH2CH2CH2OH

OH

OH
H

H
H

H
H
H

CH2
CH2

CH3CH2CH2CH2OH

CH3
CH2

CDCl3 (solvent)

OH

CH3

CH3CH2CH2CH2OH

CH2

CH2

CH2
OH

CH3

CH2

O
OH

CH2

CH2

Summary of Spectral Features

IR: O-H stretch, 3600-3000 cm-1, broad
(alcohols and phenols)
C-O stretch, 1250 to 1050 cm-1, (higher
for phenols than for alcohols)
C-NMR:

C-O, 60-65 alcohols

phenols

H-NMR:

-CH2-O, 3.5

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