Alcohol and Phenol Nomenclature

ALCOHOL AND
Sir Bernard D. Fajardo Jr

Topics:
• Physical and Chemical Properties of Alcohol and Phenol
• Uses of Alcohol and Phenol
• Classification of Alcohol
• Alcohol and Phenol Nomenclature
fajardojr.bd@shc.edu.ph
What is Alcohol?
 Alcohols: Organic compounds containing hydroxyl (-OH)

functional groups.
Condensed formula skeletal formula

symbol
Methanol (IUPAC), Methyl Alcohol (Common Name)
Alcohol
Properties of Alcohol
Physical Properties
 PHYSICAL STATES OF ALCOHOLS
- aliphatic alcohols and lower aromatic alcohols liquids at room temperature.

- highly branched alcohols and alcohols with twelve or more carbon atoms
solids.
 BOILING POINTS
i) Boiling points of alcohols are higher > alkanes and chloroalkanes of similar
relative molecular mass.
Physical Properties
For Example
C2H5OH CH3CH2CH3 CH3Cl

Relative molecular mass: 46 44 50.5
Boiling point: 78 C -42 C -24 C
- Reason:
* intermolecular hydrogen bonds
Physical Properties
 SOLUBILITY OF ALCOHOLS IN WATER
i)Alcohols with short carbon chains (i.e. methanol, ethanol) - dissolve

in water.
- dissolve in water (hydrogen bonds are formed).
ii) Solubility decreases sharply with the increasing length of the

carbon chain.
Physical Properties
 ODOR
very sharp smell
 COLOR
Colorless at room temperature
 HIGHLY VOLATILE
Easily changes into gas
Chemical Properties
Combustion
Alcohols burns in oxygen to produce carbon dioxide and water. Alcohols burn
cleanly and easily, and does not produce soot. It becomes increasingly more
difficult to burn alcohols as the molecules get bigger.
The general molecular equation for the reaction is:

CnH2n+1OH + (1.5n)O2 → (n+1)H2O + nCO2
e.g. combustion of ethanol:

C2H5OH (l) + 3 O2 (g) → 2 CO2 (g) + 3 H2O (g); (ΔHc = −1371 kJ/mol)
Chemical Properties
Dehydration
- alcohol to alkene
Dehydration of alcohols is done
by heating with concentrated
sulfuric acid, which acts as the
dehydrating agent, at 180°C. This
reaction uses alcohols to produce
corresponding alkenes and water
as byproduct.
Chemical Properties
Esterification
Alcohols can be reacted with carboxylic acid to form esters.
What is Phenol?
Aromatic compounds containing one or more

OH groups directly attached with carbon of
benzene ring.
Simplest phenol is Carbolic Acid C6H5OH
Term Phenol is derived from an old name of benzene
– Phene
Phenyl : C6H5
Properties of Phenol
- Colorless, crystalline, poisonous solid with phenolic

odor
- Melting point 41oC and Boiling Point 182oC
- Sparingly soluble in water forming pink solution at
room temperature
- Completely soluble above 68.5oC
- Causes blisters on skin
Uses of Alcohol and Phenol
Alcohol
Phenol
• The main use of phenol is as a feedstock for phenolic resins, bisphenol
A and caprolactam (an intermediate in the production of nylon-6). It is
used in the manufacture of many products including insulation
materials, adhesives, lacquers, paint, rubber, ink, dyes, illuminating
gases, perfumes, soaps and toys (IARC, 1989; WHO, 1994).
• Also used in embalming and research laboratories.
• It is a product of the decomposition of organic materials, liquid manure,
and the atmospheric degradation of benzene
• Phenol and its derivatives like dinitrophenol and pentachlorophenol
(carbolic acid) are widely used as insecticides,.
Phenol
• It is found in some commercial disinfectants, antiseptics, lotions and ointments.
• Phenol is active against a wide range of microorganisms, and there are some
medical and pharmaceutical applications including topical anesthetic and ear
drops, sclerosing agent.
• It is also used in the treatment of ingrown nails in the "nail matrix phenolization
method" (Kimata et al., 1995).
• Another medical application of phenol is its use as a neurolytic agent,
applied in order to relieve spasms and chronic pain (Wood, 1978; Geller, 1997).
• It is used in dermatology for chemical face peeling.
Classification of Alcohol
 According to the type of carbinol carbon atom (C bonded to the – OH group).
Classes:
i) Primary alcohol
- -OH group attached to a primary carbon atom
- one alkyl group attached
ii) Secondary alcohol
- -OH group attached to a secondary carbon atom
- two alkyl group attached
iii) Tertiary alcohol
- -OH group attached to a tertiary carbon atom
- three alkyl group attached
OH OH
OH
primary secondary tertiary
Alcohol Nomenclature
IUPAC RULES
1. Select the longest continuous chain of carbon atoms containing the hydroxyl
group.
IUPAC RULES
2. Number the carbon atoms in this chain so that the one bonded to the –OH group
has the lowest possible number
4 3 2 1
3 2 1
IUPAC RULES
3. Form the parent alcohol name by replacing the final –e of the corresponding alkane name by –
ol. When isomers are possible, locate the position of the –OH by placing the number (hyphenated)
of the carbon atom to which the –OH is bonded immediately before the parent alcohol name.
4. Name each alkyl branch chain (or other group) and designate its position by number
4
3 2 1
4 3 2 1
Common name: sec-isoamyl alcohol

IUPAC name: 3-methyl-2-butanol
example
5 4 3
2 1
IUPAC name: 3-methyl-2-pentanol
example
Common name: methy alcohol

IUPAC Name: methanol
Common name: ethy alcohol

IUPAC Name: ethanol
Common name: isopropyl alcohol

IUPAC Name: 2 propanol
example
Common name: tert butyl alcohol

IUPAC Name: 2-methyl-2-propanol
IUPAC Name: 2-pentanol
Nomenclature of Diols
 Alcohols with two –OH groups

 Naming of diols is like other alcohols except that the suffix diol is used
and two numbers are needed to tell where the two hydroxyl groups are
located.
3,4 - hexanediol
1,2 - ethanediol
1,3 - butanediol
6 4
3
7 2 5-ethyl-3-methyl-2,5-heptanediol
1
5
Nomenclature of Alcohol
4 – bromo- 1- pentanol
2 – bromo- 4- chloro-3- pentanol
3-pentene-2-ol
3-hexene-2,5-diol
1-heptene-5-yne-4-ol
Nomenclature of Cyclic Alcohol
 Using the prefix cyclo-

 The hydroxyl group is assumed to be on C1.
 The “1”is usually omitted from the name on the alcohol
OH cylopentanol

3-methylcyclohexanol
5-chloro-2-cyclohexenol
Cl
1,2-cyclohexanediol
Nomenclature of Phenol
 The terms ortho (1,2-disubstituted), meta (1,3- disubstituted) and

para (1,4-disubstituted) are often used in the common names.
Common name: o-bromophenol Common name: m-nitrophenol Common name: p-cresol

IUPAC Name: 2-bromophenol IUPAC Name: 3-nitrophenol IUPAC Name: 2-methylphenol
 Phenols may be monohydric, dihydric or trihydric - (number of
hydroxyl groups) in the benzene ring.
Common name: resorcinol Common name: Hydroquinone Common name: Pyrogallol

IUPAC Name: benzene 1,3-diol IUPAC Name: benzene 1,3-diol IUPAC Name: benzene 1,2,3-triol
Common Name: o-benzyl phenol

IUPAC Name: 2-benzylphenol
IUPAC Name: 2-benzyl-4-chlorophenol
Worksheet(Alcohol)
1. 4.1, 4 cyclohexane diol
5. heptanol
2.
3.
Worksheet (Phenol)
1. 2-nitro phenol
4.
2. 3-ethy phenol
5.
3. Benzene 1,3,4-triol
THANK YOU!

Alcohol and Phenol Nomenclature

Uploaded by

Document Information

Copyright

Available Formats

Share this document

Share or Embed Document

Sharing Options

Did you find this document useful?

Is this content inappropriate?

Copyright:

Available Formats

Alcohol and Phenol Nomenclature

Uploaded by

Copyright:

Available Formats

ALCOHOL AND

Sir Bernard D. Fajardo Jr

• Physical and Chemical Properties of Alcohol and Phenol

• Uses of Alcohol and Phenol

• Alcohol and Phenol Nomenclature

 Alcohols: Organic compounds containing hydroxyl (-OH)

Condensed formula skeletal formula

- aliphatic alcohols and lower aromatic alcohols liquids at room temperature.

C2H5OH CH3CH2CH3 CH3Cl

i)Alcohols with short carbon chains (i.e. methanol, ethanol) - dissolve

ii) Solubility decreases sharply with the increasing length of the

The general molecular equation for the reaction is:

e.g. combustion of ethanol:

Aromatic compounds containing one or more

- Colorless, crystalline, poisonous solid with phenolic

Common name: sec-isoamyl alcohol

IUPAC name: 3-methyl-2-pentanol

Common name: methy alcohol

Common name: ethy alcohol

Common name: isopropyl alcohol

Common name: tert butyl alcohol

IUPAC Name: 2-pentanol

 Alcohols with two –OH groups

2 – bromo- 4- chloro-3- pentanol

 Using the prefix cyclo-

 The terms ortho (1,2-disubstituted), meta (1,3- disubstituted) and

Common name: o-bromophenol Common name: m-nitrophenol Common name: p-cresol

Common name: resorcinol Common name: Hydroquinone Common name: Pyrogallol

Common Name: o-benzyl phenol

IUPAC Name: 2-benzyl-4-chlorophenol

1. 4.1, 4 cyclohexane diol

You might also like