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Chapter 11 Alcohols Phenols and Ethers - Ncert Solutions: INTEXT Questions
Chapter 11 Alcohols Phenols and Ethers - Ncert Solutions: INTEXT Questions
INTEXT Questions
Question 1.
Classify the following as primary, secondary and tertiary alcohols :
Solution:
Primary alcohols : (i), (ii) and (iii)
Secondary alcohols : (iv) and (v)
Tertiary alcohols : (vi)
Question 2.
Identify allylic alcohols in the above examples.
Solution:
Allvlir alcohols : (ii) and (vi).
Question 3.
Name the following compounds according to IUPAC system.
1. 3-Chloromethyl-2-isopropylpentan-l-ol
2. 2, 5-Dimethylhexane-1,3-diol
3. 3-Bromocyclohexanol
4. Hex-l-en-3-ol
5. 2-Bromo-3-methylbut-2-en-1 -ol
Question 4.
Show how are the following alcohols prepared by the reaction of a suitable Grignard reagent
on methanal.
Solution:
Solution:
1. Butan-1-ol
2. 2-Methylbutan-2-ol
Solution:
Question 7.
Predict the major product of acid catalysed dehydration of
1. 1-methylcyclohexanol and
2. butan-1-ol
Solution:
Question 8.
Ortho and para nitrophenols are more acidic than phenol. Draw the resonance structures of
the corresponding phenoxide ions.
Solution:
The attachment of the -NO2 group to the phenol molecule at 0- and p-positions decreases the
electron density on oxygen atom. This causes the oxygen atom to pull the bond pair of
electrons of the O – H bond towards itself thereby facilitating the release of H as H +.
Question 9.
Write the equations involved in the following reactions :
1. Reimer-Tiemann reaction
2. Kolbe’s reaction
Question 10.
Write the reactions of Williamson synthesis of 2-ethoxy-3-methylpentane starting from
ethanol and 3-methylpentan-2-ol.
Solution:
Solution:
Solution:
1. 2,2,4-Trimethylpentan-3-ol
2. 5-Ethylheptan-2,4-diol
3. Butane-2,3-diol
4. Propane-1,2,3-triol
1. 2-Methylbutan-2-ol
2. 1-Phenylpropan-2-ol
3. 3,5-Dimethylhexane-1,3,5-triol
4. 2,3-Diethylphenol
5. 1-Ethoxypropane
6. 2-Ethoxy-3-methylpentane
7. Cyclohexylmethanol
8. 3-Cydohexylpentan-3-ol
9. Cyclopent-3-en-1 -ol
10. 3-Chloromethylpentan-1-ol
Question 3.
Solution:
The boiling point of any compound depends on the strength of inter-molecular forces.
Stronger is the inter-molecular attraction, higher is the boiling point.
In butane, the molecules interact with each other through weak van der Waals forces. These
weak forces can be easily overcome by supplying small amount of heat energy. Thus, they
have low boiling point.
In propanol, the molecules are held together by strong hydrogen bonding. These attractive
forces operating between molecules are more difficult to break and therefore higher amount
of heat needs to be supplied, therefore, the higher boiling point.
Question 5.
Alcohols are comparatively more soluble in water than hydrocarbons of comparable
molecular masses. Explain this fact.
Solution:
Organic compounds are soluble in water if they are able to form hydrogen bonds with it.
Alcohols are able to establish this interaction by the virtue of their OH group and are
therefore soluble in water. On the other hand, other hydrocarbons of comparable mass do not
dissolve in water since they cannot form hydrogen bonds.
Question 6.
What is meant by hydroboration-oxidation reaction? Illustrate it with an example.
Solution:
Hydroboration-oxidation is a method of preparation of alcohols from alkenes. The main
advantage of this method is the high yield of alcohol obtained. During hydroboration,
diborane (BH3)2 is made to react with an alkene to form an addition product. This product is
then treated with hydrogen peroxide in the presence of sodium hydroxide to give alcohol.
Question 7.
Give the structure and IUPAC names of monohydric phenols of molecular formula, C 7H8O.
Solution:
Question 8.
While separating a mixture of ortho and para nitrophenols by steam distillation, name the
isomer which will be steam volatile. Give reason.
Solution:
As a result of the strong forces operating between the molecules of p-isomer, the boiling
point is higher and it is not steam volatile.
Question 9.
Give the equations of reactions for the preparation of phenol from cumene.
Solution:
Question 10.
Write chemical reaction for the preparation of phenol from chlorobenzene.
Solution:
Question 12.
You are given benzene, cone. H2SO4 and NaOH. Write the equations for the preparation of
Question 13.
Show how will you synthesise :
Question 14.
Give two reactions that show the acidic nature of phenol. Compare acidity of phenol with that
of ethanol.
Solution:
Question 15.
Explain why is ortho nitrophenol more acidic than methoxyphenol?
Solution:
From structures (I) – (V), we find that the attachment of hydroxyl group to benzene has
increased the electron density (-ve charge) on the ring carbon atoms (especially C-2, C-4 and
C-6). It is therefore said to have activated the ring towards electrophiles which are attracted to
the increased electron density.
Question 17.
Give equations of the following reactions :
Question 18.
Explain the following with an example.
(i) Kolbe’s reaction
(ii) Reimer-Tiemann reaction
(iii) Williamson ether synthesis
(iv) Unsymmetrical ether.
Solution:
(i) Kolbe’s reaction :
The fact that phenoxide ion is even more reactive than phenol towards incoming electrophiles
is made use of in this reaction. Sodium phenoxide is reacted with CO2 followed by acid
treatment to yield o-hydroxybenzoic acid as the major product.
Question 20.
How are the following conversions carried out?
Question 21.
Name the reagents used in the following reactions :
1. Alkaline KMnO4
2. Pyridinium chlorochromate in chloromethane (CH 2Cl2)
3. Br2/H2O
4. Alkaline KMnO4
5. Cone. H2SO4 or H3PO4 at 433-443 K
6. H2/Ni or NaBH4 or LiAlH4
Question 22.
Give reason for the higher boiling point of ethanol in comparison to methoxymethane.
Solution:
The higher boiling point of ethanol may be attributed to the presence of intermolecular
hydrogen bonding in it.
Due to such extensive bonding, more energy needs to be supplied to ethanol to break these
bonds and move it into the vapour phase.
Solution:
1. 1 -Ethoxy-2-methylpropane
2. 2-Chloro-l-methoxyethane
3. 4-Nitroanisole
4. 1-Methoxypropane
5. 1-Ethoxy-4,4-dimethylcyclohexane
6. Ethoxybenzene
Question 24.
Write the names of reagents and equations for the preparation of the following ethers by
Williamson’s synthesis :
1. 1-Propoxypropane
2. Ethoxybenzene
3. 2-Methyl-2-methoxypropane
4. 1-Methoxyethane
Solution:
This is because the competing elimination reaction predominates over S N2 and alkene is
formed.
Question 26.
How is 1-propoxypropane synthesised from propan-1 -ol? Write mechanism of this reaction.
Solution:
If an ether is to be formed, another alcohol molecule must carry out a nucleophilic attack on
the carbocation as
For the same reason 3° alcohols in the presence of acid do not form ethers since 3° alcohols
are even more sterically hindered than 2° alcohols.
Question 28.
Write the equation of the reaction of hydrogen iodide with :
1. 1-propoxypropane
2. methoxybenzene; and
3. benzyl ethyl ether.
Question 29.
Explain the fact that in aryl alkyl ethers (i) the alkoxy group activates the benzene ring
towards electrophilic substitution and (ii) it directs the incoming substituents to ortho and
para positions in benzene ring.
Solution:
Consider the following resonance structures of aryl alkyl ethers :
(i) From the above structures we find that the presence of the OR group has increased the
electron density on the benzene ring and therefore the ring is said to have been activated
towards incoming electrophiles.
(ii) From structures (II), (III) and (IV) we find that and the electron density has increased on
C-2, C-4 and C-6, i.e., at the ortho and para positions. As a result the electrophile (E )
attaches itself to these e- rich sites and the -OR group is said to have directed the E® to ortho
and para positions.
Question 31.
Write equations of the following reactions :
Question 33.
When 3-methylbutan-2-ol is treated with HBr, the following reaction takes place :