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ALCOHOL

CONTENTS
Introduction
Mono hydric alcohols
Nomenclature
Isomerism in alcohols
Method of preparation
Physical properties
Chemical properties
Distinguish between 1o. 2o and 3o alcohols
Structure and uses

INTRODUCTION

Alcohols are the organic compounds in which a hydroxyl (-OH) group is attached to saturated
carbon atom. Alcohols are also called as hydroxyl derivative of alkanes.

The hydroxyl group is the functional group. Alcohols containing one hydroxyl group
are called monohydric alcohols. Alcohols with two, three, or more hydroxyl groups are
known as dihydric alcohols, Trihydric Alcohols, and Polyhydric Alcohols respectively. For
example

It should be noted that in case of dihydric or trihydric alcohols, hydroxyl groups are attached
to different carbon atoms. When more than one hydroxyl group (-OH) attached to the same
carbon atom, the compound becomes unstable and therefore looses a water molecule to form
a carbonyl compound.

MONOHYDRIC ALCOHOLS
Monohydric alcohols contain one-OH group attached to a saturated carbon. They may
be represented as (R-OH).
PRIMARY (1O), SECONDARY (2O) AND TERTIARY (3O) ALCOHOLS
Monohydric alcohols are classified as primary (1o), secondary (2o) and tertiary (3o)
depending upon whether the –OH group is attached to a primary, a secondary, or a tertiary
carbon.

NOMENCLATURE
A. Common System: In common system alcohols are named as Alkyl alcohols.
For example:

B. IUPAC System: In IUPAC system alcohols are named as Alkanols. The IUPAC rules are:
a) Select the longest continuous carbon chain containing the –OH group.
b) Change the name of alkane corresponding to this chain by dropping the ending –e and
adding the suffix –ol.
c) Number the chain so as to give the carbon carrying the –OH group, the lowest
possible number. The position of the –OH group is indicated by this number.
d) Indicate the positions of other substituent’s or multiple bonds by numbers.
The examples given below show how these rules are used:
ISOMERISM IN ALCOHOLS
Alcohols exhibit chain, positional and functional isomerism.
1. Chain Isomerism. Chain isomers of alcohols differ in the length of the carbon chain
attached to the hydroxyl group.
For example alcohol with molecular formula (C4H10O)

2. Positional Isomerism. These isomers of alcohols differ in the position of hydroxyl


group in the carbon chain.
For example alcohol with molecular formula (C4H10O)

3. Functional isomerism. These isomers of alcohols differ in the functional group


present in the carbon chain.
For example alcohol with molecular formula (C4H10O)

METHODS OF PREPARATION
Alcohols are prepared by following methods:

1) Hydrolysis of alkyl halides. Alkyl halides react with aqueous sodium hydroxide to
form alcohols.

2) Hydration of alkenes. Alkenes react with sulfuric acid to alkyl hydrogen sulfates
(Markovnikov rule is followed).Alkyl hydrogen sulfates on hydrolysis give alcohols
.for example,
3) Hydrolysis of esters. Alcohols may be prepared by base or acid-catalyzed hydrolysis
of esters.

4) Reduction of aldehydes and ketones. Aldehydes and ketones can be reduced with
H2/Ni or lithium aluminium hydride to form the corresponding alcohols. Aldehydes
give primary alcohols. Ketone gives secondary alcohols.

5) Fermentation of carbohydrates. Some alcohols are prepared by fermentation of


starches and sugars under the influence of suitable microorganisms. for example,

PHYSICAL PROPERTIES:
1. Lower alcohols are colorless, toxic liquids. They have a characteristic smell. Higher
alcohols colourless solid.
2. Boiling points of alcohols increase regularly with the increase in the number of
carbon atoms.
3. Among isomeric alcohols, as branching increases the boiling points decrease.
4. Boiling points of alcohols are much higher than those of the corresponding alkanes.
This is due to formation of hydrogen bonding between alcohol molecules.

5. The first three members of alcohols are completely water soluble. Solubility decreases
with increase number of carbon atoms. Solubility is due to formation of hydrogen
bonding between alcohol molecules and water molecules.

CHEMICAL PROPERTIES
Alcohols are reactive compounds. They are attacked by polar or ionic reagents. This is
because:
 The C-O and O-H bonds of alcohols are polar since oxygen is highly electronegative.
 The oxygen atom of alcohol is an electron rich center due to presence of lone pair of
electrons.

Alcohol undergoes following reactions:


1. Reaction with active metals. Alcohols react with sodium or potassium to form alkoxides
with the liberation of hydrogen gas.

2. Reaction with Phosphorus halides. Alcohols react with phosphorus pentahalides(px3) to


form alkyl halides.

1.
2.

3. Reaction with thionyl chloride .Alcohols reacts with thionyl chloride (socl2) to form alkyl
chlorides.

4. Reaction with hydrogen halides. Alcohols react with hydrogen halides (HX) to form the
corresponding alkyl halides.

5. Reaction with Sulfuric Acid:


a) Dehydration of alcohols to alkenes. When ethyl alcohol is treated with concentrated
sulfuric acid at 170C, ethyleneis formed. Notice that only one alcohol molecule is involved in
the reaction.

Dehydration of alcohol follows Saytzeffs rule.


b) Dehydration of alcohols to ethers. When excess of ethyl alcohol is treated with
concentrated sulfuric acid at 140oc, diethyl ether is formed .notice that two alcohol molecules
are invovlved in the reaction.
6. Reaction with Carboxylic acids. Alcohols react with carboxylic acids to form esters.
Concentrated sulfuric acid is used as a catalyst. The reaction is reversible and can be shifted
in the forward direction by removing water as soon as it is formed.

7. Oxidation. Alcohols can be oxidized. The nature of the product depends on the type of
alcohol and the conditions of the reaction. Most widely used oxidizing agents are KMnO 4 +
H2SO4 orNa2Cr2O7 + H2SO4. Oxidation of alcohols can be used to distinguish between
primary, secondary, and tertiary alcohols.
Primary alcohols are first oxidized to aldehydes and then to acids. The acid contains same
number of carbon atoms as alcohol.

Notice that the acid and the alcohol contain the same number of carbon atoms. The
reaction can be stopped at the aldehyde stage by removing it from the oxidizing medium as it
is formed.
Secondary alcohols are oxidized to the corresponding ketones.

Further oxidation under very drastic conditions breaks up the ketone molecule,
producing carboxylic acids containing fewer carbon atoms per molecule.

Tertiary alcohols are stable to oxidation under normal conditions.


HOW TO DISTINGUISH BETWEEN 1O. 2O AND 3O ALCOHOLS
Lucas Test: In test, alcohols are treated with a solution of HCl and zinc chloride to form
alkyl halides. Zinc chloride serves as a catalyst.

The three types of alcohols undergo this reaction at different rates. Tertiary alcohols
react with Lucas reagent very rapidly. Secondary alcohols react somewhat slower. Primary
alcohols react with Lucas reagent even more slowly.
In practice, the Lucas test is carried out as follows: an alcohol is mixed, at room
temperature, with concentrated HCl and ZnCl2. The alkyl chloride, which is formed, is
insoluble in the medium. It causes the solution to become cloudy before it separates as a
distinct layer.
a. With Tertiary alcohols cloudiness appears immediately.
b. With Secondary alcohols cloudiness appears in 5 minutes.
c. With Primary alcohols the solution remains clear. This is because primary alcohols do
not react with Lucas reagent at room temperature. High temperature is needed.

Three types of alcohols may be distinguished by oxidation reaction also.


ETHYL ALCOHOL
Ethyl alcohol (CH3−CH2−OH), also called as Ethanol and drinking alcohol, is a volatile,
flammable, colourless liquid compound with a slight characteristic odor. It is a psychoactive
substance and is the principal type of alcohol found in alcoholic drinks. It is also called as
grain alcohol since it can be prepared from starchy grains.
Ethanol is naturally produced by the fermentation of sugars by yeasts or via petrochemical
processes, and is most commonly consumed as a popular recreational drug.

Uses
1. It is widely used as a chemical solvent, either for scientific chemical testing or in
synthesis of other organic compounds, and is a vital substance utilized across many
different kinds of manufacturing industries.
2. Ethanol is used an antiseptic and disinfectant in medical wipes and most common
antibacterial hand sanitizer gels.
3. Used in the manufacture of alcoholic beverages.
4. Ethanol may be administered as an antidote to methanol and ethylene glycol
poisoning.
5. As a central nervous system depressant, ethanol is one of the most commonly
consumed psychoactive drugs. It can lift mood, cause feelings of euphoria, decrease
anxiety, and increase sociability and talkativeness.
6. Ethanol is miscible with water and is a good general purpose solvent. It is found in
paints, tinctures, markers, and personal care products such as mouthwashes, perfumes
and deodorants.
7. Ethanol also used in the purification of DNA and RNA.
8. Ethanol is also used as an motor engine fuel and fuel additive
9. Used as a preservatives for biological specimens.
10. Because of its low melting point (−114.14 °C) and low toxicity, ethanol is sometimes
used in laboratories as a cooling bath to keep vessels at temperatures below the
freezing point of water. For the same reason, it is also used as the active fluid in
alcohol thermometers.
11. Ethyl Alcohol can be safely used as a solvent for different products such as culinary
extracts, essential oils, tinctures, and concentrates.

METHYL ALCOHOL
Methyl alcohol (CH3OH) also known as Methanol is the simplest alcohol is a light, volatile,
colourless, flammable liquid with a distinctive odor very similar to that of ethanol. Methanol
acquired the name wood alcohol because it was once produced chiefly as a by product of the
destructive distillation of wood. t is also highly flammable, and highly toxic to humans if
ingested.

Uses
1. Methanol can be used to make other useful solvents including acetic acid, dimethyl
ether, and propylene etc.
2. Methanol is used industrially as an ingredient in antifreeze mostly in automobile
radiator.
3. Used as a denaturant for ethanol.
4. With gasoline used as motor fuel.
5. It is also used for producing biodiesel by transesterification reaction.
6. One of the most common uses of methanol is as an ingredient for formaldehyde. This
chemical which can be derived from methanol is used extensively in the production of
plastics, including those used in construction materials, car parts, paints, explosives,
and wrinkle-resistant artificial fabrics.

CHLOROBUTANOL

Chlorobutanol (1, 1, 1-Trichloro-2-methyl-2-propanol) is a colour less crystalline


compound soluble in chloroform, ether and slightly soluble in water.

Uses
1. Chlorobutol is used as a sedative, hypnotic and weak local anesthetic.
2. It has antibacterial and antifungal properties.
3. Chlorobutol is used as a preservative (0.5%) in injection, eye drops, mouth washes,
creams, ointments etc.
4. Chlorobutol is used in the treatment of Mild pain on skin, Scratches, Grazes, Dental
plaque formation, Gingivitis, Oral hygiene, Mouth ulceration, and oral infections due
to fungus candida, Throat infections, Cold relief and other conditions.

CETOSTERYL ALCOHOL
Cetostearyl alcohol (CH3(CH2)nOH) also called as cetearyl alcohol or cetylstearyl alcohol
is a mixture of, consisting of cetyl and stearyl alcohols and is classified as a fatty alcohol. It
is a white, waxy, solid material in the form of flakes. It is oil soluble, but it is not water-
soluble.

Uses
1. In the pharmaceutical and cosmetics industry, used as an emulsion stabilizer,
opacifying agent, surfactant and viscosity increasing agent.
2. It is often used in creams and lotions.
3. It is commonly used in the hair conditioners and other hair products.
4. It imparts an emollient feel to the skin and can be used as a moisturizer to treat or
prevent dry, rough, scaly, itchy skin and minor skin irritations

BENZYL ALCOHOL
Benzyl alcohol (C6H5CH2OH) is an aromatic alcohol is a colourless liquid with a mild
pleasant aromatic odor. It is a useful solvent due to its polarity, low toxicity, and low vapour
pressure. Benzyl alcohol has moderate solubility in water and is miscible in alcohols and
diethyl ether.

Uses
1. Benzyl alcohol is used as a bacteriostatic preservative at low concentration in
intravenous medications, cosmetics and topical drugs.
2. Benzyl alcohol has a variety of uses in the manufacture of other benzyl compounds,
as a pharmaceutical aid, in the making of perfume, and for manufacturing flavoring
for the food industry.
3. It is used as local anesthetics and to reduce pain associated with lidocaine injection.
4. Benzyl alcohol as a 5% solution has been used for the treatment of head lice in
children older than 6 months and in adults.
5. Benzyl alcohol is an ingredient used in the manufacture of soaps, topical creams, skin
lotions, shampoos, and facial cleansers and is popular due to its anti-bacterial and
anti-fungal properties.
6. It also having antipruritic activity and used to relieve itching.
7. Benzyl alcohol is used as a general solvent for inks, waxes, shellacs, paints, lacquers,
and epoxy resin coatings.
8. In photography, benzyl alcohol develops photos.
9. It is used in a wide variety of cosmetic formulations as a fragrance component,
preservative, solvent, and viscosity-decreasing agent.
GLYCEROL
Glycerol which is also known as glycerine is a colourless, odourless, viscous liquid that is
sweet-tasting and non-toxic. Glycerol is easily soluble in water, due to the ability of the
polyol groups to form hydrogen bonds with water molecules. Glycerol is slightly denser than
water.

Uses
1. Glycerol is a very widely used component in various pharmaceutical products like
capsules, syrups, topical creams, and suppositories.
2. Glycerol is found in cough syrups, elixirs, toothpaste, mouthwashes, products of skin
care and water-based personal care lubricants.

3. In food and beverages, glycerol serves as a humectants, solvent, and sweetener, and
help preserve foods.
4. Glycerol is a component of glycerin soap and prevents skin dryness with its
moisturizing properties
5. In drug powders, glycerol is also used as a levigating agent, which helps reduce the
particle size when grinding. This helps the powders to be mixed thoroughly and
evenly with other ingredients.
6. Suppositories of glycerol can act as laxatives since they can irritate anal mucosa.
7. Its low toxicity and lack of a disagreeable odor or flavor allow the use of glycerol as
an emulsifier.
8. Vegetable glycerin with propylene glycol, in one of the common component of e-
cigarette liquid.
9. Glycerol was used as an anti-freezing agent for automotive applications.
10. Glycerol is used to produce nitroglycerin, which is an essential ingredient of various
explosives such as dynamite, gelignite, and propellants.

PROPYLENEGLYCOL
Propylene glycol (propane-1,2-diol) is a synthetic organic compound with the chemical
formula C3H8O2. It is a viscous colorless liquid which is nearly odorless but possesses a
faintly sweet taste. Chemically it is classed as a diol and is miscible with a broad range of
solvents, including water, acetone, and chloroform.

Uses
1. Propylene glycol is a commonly used as drug solubilizer in topical, oral, and
injectable medications. For medicinal purposes, propylene glycol is used as a solvent
in different formats, injectable, oral and topical.
2. It is used as stabilizer for vitamins, and as a water-miscible cosolvent.
3. Propylene glycol keeps personal care products consistent, soft and moist. This
includes deodorant sticks, sunscreen, shampoos, body lotions, face creams and
lipstick. Additionally, it works as an excipient to stabilize foam in personal care and
health care products.
4. The greatest amount of propylene glycol is found in the textile industry where it is
used in polyester fiber production.
5. Industrial-grade propylene glycol is used in industries as a heat-transfer medium that
protects against pressure burst and corrosion, controls viscosity, and dissolves active
agents.
6. Industrial propylene glycol is also used in paints and coatings for wear and weather
protection, as an aircraft de-icer, in liquid detergents, antifreeze, and as a solvent in
printing ink.
7. As a basic building block, it is used in its raw form to make formable plastics like
unsaturated polyester resins.
8. Propylene glycol may see some substitution by glycerin in antifreeze and deicing
applications as well as a replacement as a humectants in food applications.

IMPORTANT QUESTIONS
1. How are alcohols prepared?
2. Write important reactions of Alcohols.
3. Write oxidation of different Alcohols.
4. How will u distinguish between primary, secondary, and tertiary alcohols.
5. Discuss isomerism in alcohol.
6. Alcohols have higher boiling point than alkanes of camparable molecular
mass. Why?
7. Explain the solubility of alcohol, ether and alkane.
8. Discuss the application of Lucas test.
9. Discuss structure and uses of ethyl alcohol and propylene glycol.
10. What will be the product formed when 2-Pentanol dehydrated in presence of
sulphuric acid.

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