CHAPTER – 6 Monohydric alcohols can be further classified as follows:

(a) Compounds containing (Csp3−OH) bond − on this basis

Alcohols, Phenols and Ethers alcohols are of the following types −
(i) Primary Alcohols: Alcohols in which the hydroxyl (−OH)
TOPIC−1 (Intoduction and classification of alcohols) group is attached to the primary (1°) carbon atom are called primary
or 1° alcohols. Example −
Q.1 What are alcohols ?
Ans. The organic compounds formed by the replacement of one or
more hydrogen atoms by a hydroxyl (−OH)group in an aliphatic
hydrocarbon are called alcohols. (ii) Secondary alcohols: Alcohols in which the hydroxyl (−OH)
group is attached to the secondary (2°) carbon atom are called
secondary or 2° alcohols. Example −

Example −

(iii) Tertiary alcohols: Alcohols in which the hydroxyl (−OH)

group is attached to the tertiary (3°) carbon atom are called tertiary
or 3° alcohols. Example −
Q.2 Give the classification of alcohols.
Ans. Alcohols can be classified as follows:
(a) On the basis of the number of hydroxyl (−OH) group, alcohols
are of the following types−
(i) Monohydric Alcohols − Alcohols that contain a single hydroxyl
(−OH) group are called monohydric alcohols. Example − (iv) Allylic alcohols − Alcohols in which the hydroxyl (−OH)
group is attached to the next sp3&hybridized carbon atom from the
carbon–carbon double bond (C=C) are called allylic alcohols.
Example −

(ii) Dihydric alcohols − Alcohols that contain two hydroxyl (−OH)

groups are called dihydric alcohols.Example –

(iii) Trihydric alcohols − Alcohols that contain three hydroxyl

(−OH) groups are called trihydric alcohols. Example –

(v) Benzylic alcohols − Alcohols in which the hydroxyl (−OH)

group is attached to the sp3&hybridized carbon atom attached to the
aromatic ring are called benzylic alcohols. Example –
Glycerol

(iv) Polyhydric Alcohols – Alcohols that contain more than three

hydroxyl (−OH) groups are called polyhydric alcohols.
Example −

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(b) Compounds containing (Csp2−OH) bond − Alcohols in which NO. Compound Common IUPAC name
the hydroxyl (−OH) group is attached to the sp2−hybridized carbon name
atom of the carbon-carbon double bond (C=C) are called vinylic 1. Methyl Methanol
alcohols. Example − alcohol
2. n-propyl Propan-1-ol
alcohol
3. Isopropyl Propan-2-ol
alcohol
Q.3 Classify the following as primary, secondary and tertiary 4. n-butyl Butan-1-ol
alcohols: alcohol
5. sec-butyl Butan-2-ol
alcohol

6. Isobutyl 2-Methyl
alcohol propan-1-ol
7. tert-butyl 2-Methyl
alcohol propan-2-ol

8 Glycerol Propan-1,2,3-
triol

Ans. primary alcohols % ¼i½] ¼ii½] ¼iii½ Q.3 Name the following compounds according to IUPAC system.
secondary alcohols % ¼iv½] ¼v½
tertiary alcohols % ¼vi½

TOPIC−2 (Nomenclature)

Q.1 Explain nomenclature of alcohols.

Ans. Alcohols are named in two ways.
(a) In the IUPAC system – According to IUPAC system, the
name of an alcohol is derived from the name of the alkane
from which the alcohol is derived, by substituting ‘e’ of
alkane with the suffix ‘ol’. For example, CH 3OH is
methanol.
(b) In the common system − The common name of an alcohol
is derived from the common name of the alkyl group and
adding the word alcohol to it. For example, CH3OH is
methyl alcohol.

Q.2 Give the common and IUPAC names of following compounds. ¼vi½

¼vii½

¼viii½

¼ix½

Ans. Ans.

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¼i½ 3-Chloromethyl-2-isopropylpentan-1-ol to the fact that alcohols are associated via intermolecular hydrogen
¼ii½ 2, 5-Dimethylhexan-1, 3-diol bonding. For the same alcohol, as the branching increases, boiling
¼iii½ 3-Bromocyclohexan-1-ol point decreases due to decrease in surface area.
¼iv½ Hex-1-en-3-ol
(iii) Solubility of alcohols in water is due to their ability to form
¼v½ 2-Bromo-3-methylbut-2-en-1-ol
hydrogen bonds with water molecules. Several of the lower
¼vi½ 2,2,4-trimethylpentan-3-ol
molecular mass alcohols are miscible with water in all proportions.
¼vii½ 5-ethylheptan-2, 4-diol Solubility in water decreases with increase in molecular mass due to
¼viii½ Butan-2, 3-diol a decrease in the extent of intermolecular hydrogen bonding.
(ix½ Propan-1,2, 3-triol
(iv) Alcohols are weaker acids than water due to the lower polarity
Q.4 Write structures of the compounds whose IUPAC names are as of O – H bond in alcohols. The acidic strength of alcohols decreases
follows: as the number of electron donating groups increase at carbon.
(i) 2 – Methylbutan – 2 – ol
(ii) 1 – Phenylpropan – 2 – ol Q.2 Why the boiling point's of alcohol are higher than alkane.
(iii) 3, 5 – Dimethylhexane – 1, 3, 5 – triol Ans. The boiling point of an alcohol is considerably higher than the
(iv) Cyclohexylmethanol boiling points of alkanes and corresponding haloalkanes. The higher
(v) 3 – Cyclohexylpentan – 3 – ol value of boiling point of alcohol is due to the association of their
(vi) Cyclopent – 3 – en – 1 – ol molecules by hydrogen bonding.
(vii) 4-Chloro-3-ethylbutan-1-ol.
Ans.

Q.3 Explain why propanol has higher boiling point than that of the
hydrocarbon, butane?
Ans. Propanol forms intermolecular H-bonds because of the
presence of -OH group while butane cannot. To break these bonds,
extra energy will be required. This causes a higher boiling point for
propanol as compared to butane.

(iv)
Q.4 Alcohols are comparatively more soluble in water than
hydrocarbons of comparable molecular masses. Explain this fact.
Ans. Alcohols form hydrogen bonds with water due to the presence
(v)
of –OH group whereas hydrocarbons cannot. Due to this inter
molecular hydrogen bonding, alcohols are more soluble in water.

Q.5 Give a reason for the higher boiling point of ethanol in

comparison to methoxymethane.
Ans. Ethanol experiences intermolecular H–bonding because of the
(vi)
presence of – OH group, which results in the association of molecules.
additional energy is necessary to break these hydrogen bonds.
Conversely, methoxymethane does not experience H – bonding.
Therefore, ethanol has a higher boiling point when compared to
methoxymethane
(vii)

Q.6 Arrange the following sets of compounds in order of their

TOPIC−3 (Nomenclature) increasing boiling points:
(a) Pentan-1-ol, butan-1-ol, butan-2-ol, ethanol, propan-1-ol,
Q.1 Write physical properties of monohydric alcohols.
methanol.
Ans. (i) Lower alcohols are liquid at room temperature while higher
ones are solid. (b) Pentan-1-ol, n-butane, pentanal, ethoxyethane.
Ans. (a) Methanol, ethanol, propan-1-ol, butan-2-ol, butan-1-ol,
(ii) The boiling point of alcohols is higher than hydrocarbons, ethers, pentan-1-ol.
and haloalkanes with the same number of carbon atoms. This is due
(b) n-Butane, ethoxyethane, pentanal and pentan-1-ol.

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TOPIC−4 (chemical properties of alcohols)

Q.1 Write chemical properties of alcohols.

Ans.The reactions of alcohols may be divided into the following
categories:
A. Reactions involving cleavage of C – OH Bond −
(i) Reaction with hydrogen halide : Alcohol on reaction with
hydrogen halide (HBr,HCl) form alkyl halides and water.

Example −

(ii) Reaction with phosphorus halide : Alcohol on reaction with

phosphorus halide form alkyl halides.

R-OH + PCl5 → R-Cl + POCl3 + HCl

3 ROH  PCl 3  3 RCl  H 3 PO 3

Alcohol Phosphorus Alkyl Phosphorus
trichlori de chloride acid

Q.2 Write Victor Meyer method to distinguish primary, secondary

and tertiary alcohol.
Ans. Victor Meyer suggested the idea of determining the primary, Q.3 What is Lucas reagent ? Give its application.
secondary or tertiary alcohol. In this method the sample alcohol is Ans. Solution of ZnCl2 in cone.HC1 is known as Lucas reagent.
treated with HI to get the iodoalkane which is again treated with
Application : It is used to differentiate primary, secondary and
AgNO2 to get the nitroalkane. The nitroalkane is then treated
tertiary alcohols. On adding the alcohol to Lucas reagent, a tertiary
with nitrous acid. The resulting solution is treated with NaOH or
alcohol reacts immediately forming a ppt of alkyl chloride. If the
KOH and the colour is observed. The red, blue and no colour
ppt. appears after few minutes, the alcohol is secondary. If no ppt. is
indicates the primary, secondary and tertiary alcohol respectively.
obtained in cold the alcohol is primary.
(i) Primary alcohol does not react with lucas reagent at room
temperature and hence no formed any oily layer.

(ii) Secondary alcohols form this oily layer within about five minutes.

(iii) Tertiary alcohols immediately form an oily layer of alkyl halide

with this reagent

Q.23 Differentiate primary, secondary and tertiary alcohol by

dehydrogenations method.
Ans. Dehydrogenation - Different type of alcohols give different products when
their vapours are passed over heated (300°C) copper metal:

(i) Primary alcohols undergo dehydrogenation to give aldehydes

(ii) Secondary alcohols undergo dehydrogenation to give ketones.

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(iii) Tertiary alcohols however undergo dehydration to form alkenes.

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