phenomenal

phenols!

“We’re getting a bit aromatic

today!”
 What are phenols?
Phenol is an aromatic organic compound with the molecular formula
C₆H₅OH. It is a white crystalline solid that is volatile. The molecule
consists of a phenyl group bonded to a hydroxy group. Mildly acidic,
it requires careful handling because it can cause chemical burns.

They are not alcohols!! Alcohols usually feature the hydroxyl group
attached to aliphatic hydrocarbons. Phenols usually contain aromatic
hydrocarbons. In comparison to phenol, alcohols are known to be less
acidic. Phenols are relatively more acidic in nature and should, therefore,
be diluted before usage.
 structure & nomenclature

Nomenclature:
Structure: 1. Common Names:
Phenols are compounds with a Simple names like phenol, cresol, catechol.
hydroxyl group (–OH) directly attached 2. IUPAC Names:
Number the ring with –OH as position 1.
to an aromatic benzene ring. Example: 2-methylphenol for o-cresol.
3. Ortho, Meta, Para (o-, m-, p-) System:
General formula: Ar–OH o- = 1,2-position
m- = 1,3-position
p- = 1,4-position
Example: Phenol (C₆H₅OH) Example: p-nitrophenol = 4-nitrophenol
 physical properties
Phenol is a colorless, crystalline, and deliquescent solid.
Melting point: 41°C | Boiling point: ~182°C (due to strong hydrogen bonding)
Solubility:
Slightly soluble in water at room temperature (forms a pink solution); fully soluble at 65.9°C.
Solubility decreases with bulkier aryl groups.
Hydrogen Bonding:
Phenol exhibits strong intermolecular hydrogen bonding, leading to a higher boiling point
than similar hydrocarbons and aryl halides.
Can form hydrogen bonds with water, aiding solubility.
More acidic than alcohols due to the sp²-hybridized carbon pulling electron density from the
–OH group.
Acidity:
Phenol ionizes more easily than alcohols, forming phenoxide ions with metals like Na or K.
pKa: 9.95 in water, 2.91 in acetonitrile.
 Acidity of phenols
Phenols are more acidic than alcohols because their
conjugate base, the phenoxide ion, is stabilized by
resonance with the aromatic ring. This spreads out
the negative charge, making the ion more stable. In
contrast, alkoxide ions from alcohols don’t have this
resonance, so the charge stays on the oxygen,
making them less stable. A more stable conjugate
base means a stronger acid.
 reaction of phenols (part 1)
1. Acidic Nature
• Phenols are weakly acidic and can donate a proton (H*) to form phenoxide ions.
C6H5OH+ NaOH —> C6H5O-Na* + H2O
• Phenol does not react with sodium bicarbonate (NaHCO3), unlike carboxylic acids.
2. Electrophilic Substitution Reactions
Due to the -OH group activating the ring, phenol undergoes electrophilic aromatic
substitution mainly at the ortho and para positions.
a. Nitration
C6H5 OH + HNO3 —> o - nitrophenol + p - nitrophenol
Dilute HNO3 mono-nitration
Concentrated HNO3:tri-nitration
b. Halogenation
C6H5OH + Br2 —> 2,4,6 - tribromophenol + HBr
• No Lewis acid catalyst needed due to high reactivity.
c. Sulfonation
C6H5OH + H2SO4 —> 0 - /p - sulfonic acid
 reaction of phenols (part 2)
3. Reimer-Tiemann Reaction
• When phenol is treated with chloroform (CHCl) and aqueous NaOH, a formyl
group (-CHO) is introduced at the ortho position.
C6H5OH + CHCl3 + 3NaOH —> o - hydroxybenzaldehy
4. Kolbe's Reaction
• Phenol reacts with CO2 in the presence of NaOH under pressure to form salicylic
acid (o-hydroxybenzoic acid).
C6H5OH + NaOH + CO2—> o - hydroxybenzoic acid
5. Oxidation
• Phenol can be oxidized to quinones (like p-benzoquinone) under strong oxidizing
conditions.
 Uses of phenols
1. Disinfectants and Antiseptics:
4. Pharmaceutical Industry:
Phenol has strong antiseptic properties, so it's used in
making disinfectants like Lysol and other cleaning agents. It's used in the production of certain medicines
like pain relievers and antiseptics.
2. Chemical Synthesis:
It is a key raw material for producing other chemicals 5. Cosmetics Industry:
such as:
In small amounts, phenol is used in some
•Bakelite (a type of plastic).
•Aspirin (acetylsalicylic acid). cosmetic products as a preservative or
•Dyes and pigments disinfectant for tools.
•Pesticides and herbicides.
6. Protein and DNA Analysis:
3. Resins Manufacturing:
Phenol is used in laboratories to purify proteins
Phenol reacts with formaldehyde to make phenol-
formaldehyde resins, used in adhesives, coatings, and and extract DNA, especially in molecular biology
insulation techniques.
 Environmental & health aspects
Phenol, a byproduct of industrial processes, harms
aquatic life such as algae, protozoa, invertebrates,
and vertebrates by reducing fertility, survival of
young, and growth. Its toxicity is influenced by
environmental and biological factors. Phenol is also
widely used in industry and can be absorbed through
the skin or lungs. While the body can detoxify small
amounts, high exposure can be fatal, especially to
infants. Although phenol promotes tumors, it is not
classified as a carcinogen, cocarcinogen,
teratogen, or likely a mutagen.
 Conclusion

To conclude, Phenol is an extremely important

compound. It helped to both kill and save human lives
While it was used as a toxic gas by cynical
organizations like the Nazis to exterminate prisoners, it
helped to revolutionize the scientific world into what it
is today.
 students
1-mayar mohamed aiad
2-mayar mohamed salah
3-Mostafa Mahmoud Badr
4-malak yousef abd elhamied
5-Hana Ahmed Bahbah
6-Hana Mohamed Elshafei
7-Manar Mohamed ahmed
8-Malak Khaled saad
9-ali fathy mohamed
 References
1. NCERT book – chemistry book 7. D.G. Alexander et al.
2. LibreTexts – Free online chemistry The selection and limitations of phenol as a reference
toxicant to detect differences in sensitivity among groups
notes. of rainbow trout (Salmo gairdneri) Water Res.
3. Morrison and Boyd – College-level 8. G.E. Blackman et al.
The physiological activity of substituted phenols. I.
chemistry book. Relationships between chemical structure and
4. Peter Sykes – Book for learning physiological activity
9. Arch. Biochem. Biophys.V.M. Brown
reaction steps (mechanisms).
The calculation of the acute toxicity of mixtures of
5. OpenStax – Free online textbook. poisons to rainbow trout Water Res.
6. BYJU’S / Toppr – explanations for 10. V.M. Brown et al.
The effect of temperature on the acute toxicity of phenol
students online. to rainbow trout in hard water Water Res.