1

Class 12th || (CHEMISTRY)

Alcohol, Phenol and Ether
NCERT Solutions

7.1 Classify the following as primary, secondary and

tertiary alcohols:
[NCERT Page-195] (iii)
CH3
| (iv) H2C = CH − CH − CH2 − CH2 − CH3
(i) CH3 − C − CH2OH |
| OH
CH3
(ii) H2C = CH − CH2OH (v) CH3 − C = C − CH2OH
| |
(iii) CH3 − CH2 − CH2 − OH CH3Br
[NCERT Page-198]
Sol. (i) 3-Ch loromethyl-2-isopropylpentan-1-ol
(ii) 2, 5-Dimethylhexane-1, 3-diol
(iv) (iii) 3-Bromocyclohexanol
(iv) Hex-l-en-3-ol
(v) 2-Bromo-3-methylbut-2-en-l-ol
(v)
7.4 Show how are the following alcohols prepared by
the reaction of a suitable Grignard reagent on
methanal?
(vi)

Sol. Primary alcohol → (i), (ii), (iii)

Secondary alcohol → (iv), (v) (i) CH3 − CH − CH2 OH (ii)
Tertiary alcohol → (vi) |
CH3
7.2 Identify allylic alcohols in the above examples. [NCERT Page-203]
[NCERT Page-195] Sol. (i)
Sol. The alcohols given in (ii) and (vi) are allylic
alcohols.

7.3 Name the following compounds according to

IUPAC system.
CH2OH
|
(i) CH3 − CH2 − CH − CH − CH − CH3
| |
CH2Cl CH3
CH2OH (ii)
|
(ii) CH3 − CH − CH2 − CH − CH − CH3
| |
CH3 OH

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7.5 Write structures of the products of the following OH

reactions: |
HCl−ZnCl2
(ii) CH3 − CH2 − C − CH3 ⎯⎯⎯⎯⎯ →
H2O/H +
(i) CH3 − CH = CH2 ⎯⎯⎯⎯ → |
CH3
2-Methylbutan-2-ol (3º)

Cl
(ii) |
CH3 − CH2 − C − CH3 + H2O
NaBH |
(iii) CH3 − CH2 − CH − CHO ⎯⎯⎯⎯
4→
CH3
| 2-Chloro-2-Methylbutane
CH3 (White turbidity)

[NCERT Page-203] Tertiary alcohols react immediately with

+ Lucas’ reagent.
H2O/H
Sol. (i) CH3 − CH = CH2 ⎯⎯⎯⎯ → CH3 − CH − CH3
Pr opene | (b) (i) CH3CH2CH2 OH + HBr
OH Butan-1-ol
Pr opene−2−ol
−H2O
⎯⎯⎯→ CH3CH2CH2CH2Br
1-Bromobutane
(ii)
OH
|
(ii) CH3 − CH2 − C − CH3 + HBr
|
CH3
2-Methylbutan-2-ol (3º)

Br
|
→ CH3 − CH2 − C − CH3 + H2O
NaBH4
(iii) CH3 − CH2 − CH − CHO ⎯⎯⎯⎯ → |
| CH3
CH3 2-Bromo-2-Methylbutane
2-Methylbutanal

CH3 − CH2 − CH − CH2OH (c) (i) CH3CH2CH2 CH2OH + SOCl2

| Butan-1-ol
CH3
2-Methylbutan-1-ol → CH3CH2CH2CH2 Cl + SO2 + HCl
1-chlorobutane

7.6 Give structures of the products you would expect

OH
when each of the following alcohol reacts with (a) |
HCl –ZnCl2 (b) HBr and (c) SOCl2. (ii) CH3 − CH2 − C − CH3 + SOCl2 →
(i) Butan-l-ol |
(ii) 2-Methylbutan-2-ol CH3
2-Methylbutan-2-ol
[NCERT Page-203]
Sol. (a) (i) CH3 − CH2 − CH2 − CH2 − OH
Butan-1-ol
Cl
|
HCl.ZnCl2
⎯⎯⎯⎯⎯ → Noreaction → CH3 − CH2 − C − CH3 + SO2 + HCl
Primary alcohols do not react |
CH3
appreciably with Lucas’ reagent (HCl– 2-Chlro-2-Methylbutane
ZnCl2) at room temperature.

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7.7 Predict the major product of acid catalysed 7.9 Write the equations involved in the following
dehydration of reactions:
(i) 1-methylcyclohexanol and (i) Reimer - Tiemann reaction
(ii) butan-l-ol (ii) Kolbe's reaction
[NCERT Page-203] [NCERT Page-203]
Sol. (i) Sol. (i) Reimer-Tiemann reaction

(ii) CH3 CH2CH2CH2 OH

Butan-1-ol
Dehydration/H+
⎯⎯⎯⎯⎯⎯→ CH3CH = CHCH3 + H2O
But-2-ene
(Major product)

7.8 Ortho and para nitrophenols are more acidic than (ii) Kolbe’s reaction
phenol. Draw the resonance structures of the
corresponding phenoxide ions.
[NCERT Page-203]

Sol.

Resonance structure of the phenoxide ion

7.10 Write the reactions of Williamson synthesis of 2-

ethoxy-3-methylpentane starting from ethanol and
3-methylpentan-2-ol.
[NCERT Page-220]
Sol. In Williamson synthesis, an alkyl halide reacts
with an alkoxide ion. Also, it is an SN2 reaction. In
the reaction, alkyl halides should be primary
Resonance structures of p-nitrophenoxide ion having the least steric hindrance. Hence, an alkyl
halide is obtained from ethanol and alkoxide ion
from 3mothylpentan-2-ol.
HBr
C2H5OH ⎯⎯⎯ → C2H5Br
Ethanol Bromoethane

CH3 − CH2 − CH − CH − CH3

| |
CH3 OH
e-Methylpentan-2-ol
Resonance structures of m-nitrophenoxide ion.
Na
It can be observed that the presence of nitro ⎯⎯→ CH3 − CH2 − CH − CH − ONa
| |
groups increases the stability of phenoxide ion. CH3 CH3
Sodium 3-Methylpentan-2-oxide

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CH3 − CH2 − CH − CH − ONa + C2H5Br

| |
CH3 CH3
⎯⎯
→ CH3 − CH2 − CH − CH − OC2H5 + NaBr
| |
HI
CH3 CH3 (iv) (CH3 )3 C − OC2H5 ⎯⎯→
2-Ethoxy-3-methylpentane tert -Butyl ethyl ether
(CH3 )3 C − I + C2H5OH
7.11 Which of the following is an appropriate set of tert -Butyliodide Ethanol
reactants for the preparation of l-methoxy-4-
nitrobenzene and why?
Exercise
CH3
(i) (ii) |
7.1 (i) CH3 − CH − CH − C − CH3
| | |
[NCERT Page-221] CH3 OH CH3
Sol. Set (ii) is an appropriate set of reactants for the (ii) H3C − CH − CH2 − CH − CH − CH2 − CH3
preparation of 1-methoxy-4 nitrobenzene. | | |
OH OH C2 H5
(iii) CH3 − CH − CH − CH3
| |
OH OH
(iv) HO − CH2 − CH − CH2 − OH
|
In set (i), sodium methoxide (CH3Ona) is strong OH
nucleophile as well as a strong base. Hence, an
elimination reaction predominates over a
substitution reaction. (v) (vi)

7.12 Predict the products of the following reactions:

(i) CH3 − CH2 − CH2 − O − CH3 + HBr →
(vii) (viii)
(ii)

(iii) (ix) CH3 − O − CH2 − CH − CH3

|
HI
(iv) (CH3 )3 C − OC2H5 ⎯⎯→ CH3
[NCERT Page-221] (x) C6H5 − O − C2H5
Sol. (i)
HBr
CH3 − CH2 − CH2 − O− CH3 + HBr ⎯⎯⎯ → (xi) C6H5 − O − C7H15 (n−)
n-propylmethyl ether
(xiii) CH3 − CH2 − O − CH − CH2 − CH3
CH3 − CH2 − CH2 − OH +CH3 − Br |
Propanol Bromomethane CH3

(ii) [NCERT Page-213]

Sol. (i) 2, 2,4-Trimethylpentan-3-ol

(iii) (ii) 5-Ethylheptane-2,4-diol
(iii) Butane-2, 3-diol
(iv) Propane-1, 2,3-triol
(v) 2-Methylphenol

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(vi) 4-Methylphenol
(vii) 2, 5-Dimethylphenol (viii)
(viii) 2,6-Dimethylphenoi
(ix) l-Methoxy-2-methylpropane
(x) Ethoxybenzene
(xi) 1-Phenoxyheptane (ix)
(xii) 2-Ethoxybutane
CH2Cl
|
7.2 Write structures of the compounds whose IUPAC (x) CH3 − CH2 − CH − CH2 − CH2 − OH
names are as follows:
(i) 2-Methylbutan-2-ol 7.3 (i) Draw the structures of all isomeric alcohols
(ii) l-Phenylpropan-2-ol of molecular formula C5H12O and give their
(iii) 3.5-Dimethylhexane -1. 3. 5-triol IUPAC names.
(ii) Classify the isomers of alcohols in question
(iv) 2.3 - Diethylphenol
11.3 (i) as primary, secondary and tertiary
(v) 1-Ethoxypropane
alcohols.
(vi) 2-Ethoxy-3-methylpentane [NCERT Page-213]
(vii) Cyclohexylmethanol Sol. (i) The structures of all isomeric alcohols of
(viii) 3-Cyclohexylpentan-3-ol molecular formula, C5H10O are shown below:
(ix) Cyclopent-3-cn-l-ol (a) CH3 − CH2 − CH2 − CH2 − CH2 − OH
(x) 4-Chloro-3-ethylbutan-l-ol. pentan-1-ol(1º)

[NCERT Page-213] (b) CH3 − CH2 − CH − CH2 − OH

|
CH3
OH 2−Methylbu tan −1−ol(1º)
|
Sol. (i) OR CH3 − C − CH2 − CH3 (c) CH3 − CH − CH2 − CH2 − OH
| |
CH3 CH3
3−Methylbu tan −1−ol(1º)
CH3
(ii) |
(d) CH3 − C − CH2 − OH
OH OH |
| | CH3
(iii) HO − CH2 − CH2 − C − CH2 − C − CH3 2, 2-Dimethylpropan-1-ol(1º)
| |
CH3 CH3 OH
|
(e) CH3 − CH2 − CH2 − CH− CH3
Pentan-2-ol (2º)
(iv) CH3 OH
| |
(v) CH3 − CH2 − O − CH2 − CH2 − CH3 (f) CH3 − CH − CH − CH3
3-methylbutan-2-ol (2º)
CH3 OH
| |
(vi) CH3 − CH2 − O − CH − CH − CH2 − CH3 (g) CH3 − CH2 − CH − CH2 − CH3
| Pentan-3-ol-(2º)
CH3
OH
|
(h) CH3 − CH2 − C − CH3
(vii) |
CH3
2-Methylbutan-2-ol-(3º)

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(ii) Primary alcohol: Pentan-l-ol;

2-Methylbutan-l-ol;
Secondary alcohol: Pentan-2-ol;
3-Methylbutan-2-ol;
Pentan-3-ol
Tertiary alcohol: 2-methylbutan-2-ol

7.4 Explain why propanol has higher boiling point

than that of the hydrocarbon, butane?
[NCERT Page-213] 7.7 Give the structures and IUPAC names of
Sol. Propanol undergoes intermolecular H-bonding monohydric phenols of molecular formula.
because of the presence of -OH group. On the C7H8O.
other hand, butane does not. [NCERT Page-213]

Sol.
Therefore, extra energy is required to break
hydrogen bonds. For this reason, propanol has a
higher boiling point than hydrocarbon butane.

7.8 While separating a mixture of ortho and para

7.5 Alcohols are comparatively more soluble in water
nitrophenols by steam distillation, name the
than hydrocarbons of comparable molecular
isomer which will be steam volatile. Give reason.
masses. Explain this fact.
[NCERT Page-213]
[NCERT Page-213] Sol. Intramolecular H-bonding is present in o-
Sol. Alcohols form H-bonds with water due to the
nitrophenol and p-nitrophenol. In pnitrophenol,
presence of –OH group. However, hydrocarbons
the molecules are strongly associated due to the
cannot form H-bonds with water.
presence of intermolecular bonding.
Hence, o-nitrophenol is steam volatile.

As a result, alcohols are comparatively more

soluble in water than hydrocarbons of comparable
molecular masses.

7.6 What is meant by hydroboration-oxidation

reaction? Illustrate it with an example. 7.9 Give the equations of reactions for the preparation
[NCERT Page-213] of phenol from cumene.
Sol. The addition of borane followed by oxidation is
[NCERT Page-213]
known as the hydroboration-oxidation reaction. Sol. To prepare phenol, cumene is first oxidized in the
For example, propan-1-ol is produced by the presence of air of cumene hydroperoxide.
hydroboration-oxidation reaction of propene. In
this reaction, propene reacts with diborane (BH3)2
to form trialkyl borane as an addition product.
This addition product is oxidized to alcohol by
hydrogen peroxide in the presence of aqueous
sodium hydroxide.

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Then, cumene hydroxide is treated with dilute acid 7.12 You are given benzene, cone. H2SO4 and NaOH.
to prepare phenol and acetone as byproducts. Write the equations for the preparation of phenol
using these reagents.
[NCERT Page-213]
Sol.

7.10 Write chemical reaction for the preparation of

phenol from chlorobenzene.
[NCERT Page-213]
Sol. Chlorobenzene is fused with NaOH (at 623 K and
320 atm pressure) to produce sodium phenoxide,
which gives phenol on acidification.

7.13 Show how will you synthesise:

(i) 1-phenylethanol from a suitable alkene.
7.11 Write the mechanism of hydration of ethene to (ii) cyclohexylmethanol using an alkyl halide by
yield ethanol. an SN2 reaction.
[NCERT Page-213]
(iii) pentan-1-ol using a suitable alkyl halide?
Sol. The mechanism of hydration of ethene to form
[NCERT Page-213]
ethanol involves three steps.
Step 1: Sol. (i) By acid-catalyzed hydration of ethylbenzene
Protonation of ethene to form carbocation by (styrene), 1-phenylethanol can be Synthesized.
electrophilic attack of H3O+:

(ii) When chloromethylcyclohexane is treated

with sodium hydroxide, cyclohexylmethanol
Step 2: is obtained.
Nucleophilic attack of water on carbocation:

Step 3: (iii) When 1-chloropentane is treated with NaOH,

Deprotonation to form ethanol: pentan-1-ol is produced.

CH3CH2CH2CH2 CH2Cl + NaOH ⎯⎯

→
1-Chloropentane

CH3CH2CH2 CH2CH2OH + NaCl

Pantan-1-ol

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7.14 Give two reactions that show ^ acidic nature of 7.16 Explain how docs the –OH group attached to a
phenol. Compare acidity of phenol with that of carbon of benzene ring activate it towards
ethanol. electrophilic substitution?
[NCERT Page-213]
[NCERT Page-213]
Sol. The acidic nature of phenol can be represented by
Sol. The -OH group is an electron-donating group. Thus,
the following two reactions:
(i) Phenol reacts with sodium to give sodium it increases the electron density in the benzene ring
phenoxide, liberating H2. as shown in the given resonance structure of phenol.

As a result, the benzene ring is activated towards

(ii) Phenol reacts with sodium hydroxide to give
electrophilic substitution.
sodium phenoxide and water as by products.

7.17 Give equations of the following reactions:

(i) Oxidation of propan-1-ol with alkaline
KMnO4, solution.
The acidity of phenol is more than that of ethanol. (ii) Bromine in CS2 with phenol.
This is because after losing a proton, the phenoxide (iii) Dilute HNO3 with phenol.
ion undergoes resonance and gets stabilized whereas (iv) Treating phenol with chloroform in presence
ethoxide ion does not.
of aqueous NaOH.
[NCERT Page-213]
alk KMnO4
Sol. (i) CH3CH2CH2OH ⎯⎯⎯⎯⎯ →CH3CH2COOH
Propan-1-ol Propanoic acid

7.15 Explain why is ortho nitrophenol more acidic than

ortho methoxyphenol? (ii)
[NCERT Page-213]
Sol.

(iii)

The nitro-group is an electron-withdrawing group.

The presence of this group in the ortho position
decreases the electron density in the O–H bond. As a
result, it is easier to lose a proton. Also, the o-
nitrophenoxide ion formed after the loss of protons is (iv)
stabilized by resonance. Hence, ortho nitrophenol is
a stronger acid.
On the other hand, methoxy group is an electron-
releasing group. Thus, it increases the electron
density in the O–H bond and hence, the proton
cannot be given out easily.
For this reason, ortho-nitrophenol is more acidic than
ortho-methoxyphenol.

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7.18 Explain the following with an example. This reaction involves SN2 attack of the
(i) Kolbe's reaction. alkoxide ion on the alkyl halide. Better results
(ii) Reimer-Tiemann reaction. are obtainedin case of primary alkyl halides.
(iii) Williamson ether synthesis.
(iv) Unsymmctrical ether.
[NCERT Page-213]
Sol. (i) When phenol is treated with sodium hydroxide,
If the alkyl halide is secondary or tertiary, then
sodium phenoxide is produced. This sodium
elimination competes over substitution.
phenoxide when treated with carbon dioxide,
(iv) Unsymmetrical ether: An unsymmetrical ether
followed by acidification, undergoes
is an ether where two groups on the two sides of
electrophilic substitution to give ortho-
an oxygen atom differ (i.e., have an unequal
hydroxybenzoic acid as the main product. This
number of carbon atoms). For example: ethyl
reaction is known as Kolbe's reaction.
methyl ether (CH3 – O – CH2CH3).

7.19 Write the mechanism of acid dehydration of

ethanol to yield ethene.
[NCERT Page-213]
(ii) When phenol is treated with chloroform
(CHC13) in the presence of sodium hydroxide, Sol. The mechanism of acid dehydration of ethanol to
a-CHO group is introduced at the ortho position yield ethene involves the following three steps:
of the benzene ring. Step 1:
Protonation of ethanol to form ethyl oxonium ion:

This reaction is known as the Reimer-Tiemann

reaction.
The intermediate is hydrolyzed in the presence Step 2:
of alkalis to produce salicyclaldehyde. Formation of carbocation (rate determining step):

Step 3:
Elimination of a proton to form ethene:

(iii) Williamson ether synthesis is a laboratory

method to prepare symmetrical and,
unsymmetrical ethers by allowing alkyl halides
The acid consumed in step 1 is released in Step 3.
to react with sodium alkoxides.
After the formation of ethene, it is removed to
shift the equilibrium in a forward direction.

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7.20 How are the following conversions carried out? 7.21 Name the reagents used in the following reactions:
(i) Propene → Propane-2-ol. (i) Oxidation of a primary alcohol to carboxylic
(ii) Benzyl chloride → Benzyl alcohol. acid.
(ii) Oxidation of a primary alcohol to aldehyde.
(iii) Ethyl magnesium chloride → Propan-1-ol.
(iii) Bromination of phenol to 2.4.6-
(iv) Methyl magnesium bromide → 2-
tribromophenol.
Methylpropan-2-ol. (iv) Benzyl alcohol to benzoic acid.
[NCERT Page-213] (v) Dehydration of propan-2-ol to propene.
Sol. (i) If propene is allowed to react with water in (vi) Butan-2-one to butan-2-ol.
the presence of an acid as a catalyst, then [NCERT Page-213]
propan-2-ol is obtained. Sol. (i) Acidified potassium permanganate
(ii) Pyridinium chlorochromate (PCC)
H+
CH3 − CH = CH2 + H2O CH3 − CH − CH3 (iii) Bromine water
Propene |
OH (iv) Acidified potassium permanganate
Propan-2-ol
(v) 85% phosphoric acid
(ii) If benzyl chloride is treated with NaOH (vi) NaBH4 or LiAIH4
(followed by acidification) then benzyl
7.22 Give reason for the higher boiling point of ethanol
alcohol is produced.
in comparison to methoxymethane.
[NCERT Page-213]
Sol. Ethanol undergoes intermolecular H-bonding due
to the presence of-OH group, resulting in the
association of molecules. Extra energy is required
(iii) When ethyl magnesium chloride is treated
to break these hydrogen bonds.
with methanal, an adduct is the produced
On the other hand, methoxymethane does not
which gives propan-1-ol on hydrolysis.
undergo H-bonding.
Hence, the boiling point of ethanol is higher than
that of methoxymethane.

7.23 Give IUPAC names of the following ethers:

(i) C2 H5OCH2 − CH − CH3
|
(iv) When methyl magnesium bromide is treated CH3
with propane, an adduct is the product which (ii) CH3OCH2CH2Cl
gives 2-methylpropane-2-ol on hydrolysis. (iii) O2 N − C6H4 − OCH3 ( p)
(iv) CH3CH2CH2OCH3

(v)

(vi)

[NCERT Page-213]

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Sol. (i) l-Ethoxy-2-methylpropane Sol. The reaction of Williamson synthesis involves SN2
(ii) 2-Chloro-1-methoxyethane attack of an alkoxide ion on a primary alkyl halide.
(iii) 4-Nitroanisole CH3
(iv) 1-Methoxypropane | +
CH3 − C − O Na + CH3 − Cl →
(v) l-Ethoxy-4, 4-dimethylcyclohexane |
(vi) Ethoxybenzene CH3
CH3
7.24 Write the names of reagents and equations for the |
preparation of the following ethers by CH3 − O − C − CH3 + NaCl
|
Williamson's synthesis: CH3
(i) 1-Propoxy propane
But if secondary or tertiary alkyl halides are taken
(ii) Ethoxybcnzcnc
in place of primary alkyl halides, then elimination
(iii) 2-Methoxy-2-methylpropane
would compete over substitution. As a result,
(iv) 1-Methoxyethane
alkenes would be produced. This is because
[NCERT Page-213]
alkoxides are nucleophiles as well as strong bases.
Sol. (i) CH3CH2CHONa + CH3CH2CH2Br ⎯⎯
→ Hence, they react with alkyl halides, which results
Sodium propoxide 1-Bromopropane
in an elimination reaction.
C2H5 CH2 − O − CH2C2H5 + NaBr CH3
1-Propoxypropane |
CH3 − C − Cl NaO − CH3 →
|
CH3
Tertiary alkyl halide
(ii)
CH3 − C = CH2 + CH2OH + NaCl
|
CH3
Alkene
CH3
|
(iii) CH3 − C − ONa + CH3 − Br → 7.26 How is 1-propoxypropane synthesised from
| Bromomethane propan-1-ol? Write mechanism of this reaction.
CH3
Sodium 2-methyl [NCERT Page-213]
-2-propoxide Sol. 1-propoxypropane can be synthesized from
propan-1-ol by dehydration. Propan-1-ol
CH3
| undergoes dehydration in the presence of protic
CH3 − C − OCH3 + NaBr acids (such as H2SO4, H3PO4) to give 1-
| propoxypropane.
CH3 +
2-methyl-2-methylpropane H
2CH3CH2CH2 − OH ⎯⎯ ⎯
→
Propane-1-ol
(iv) CH3CH2 − ONa + CH3 − Br → CH3CH2CH2 − O− CH2CH2CH3
Sodium ethoxide Bromomethane 1-Propoxypropane
CH3CH2 − O − CH3 + NaBr The mechanism of this reaction involves the
1-methoxyethane
following three steps:
7.25 Illustrate with examples the limitations of
Step 1: Protonation
Williamson synthesis for the preparation of certain H+
types of ethers. CH3CH2CH2 − O − H+ → CH3CH 2CH 2 − O − H
[NCERT Page-213] Popan-1-ol

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Step 2: Nucleophilic attack 7.29 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.
[NCERT Page-213]
Sol. (i)

Step 3: Deprotonation

In aryl alkyl ethers, clue to the +R effect of

the alkoxy group, the electron density in the
benzene ring increases as shown in the
7.27 Preparation of ethers by acid dehydration of following resonance structure.
secondary or tertiary alcohols is not a suitable
method. Give reason.
[NCERT Page-213]
Sol. The formation of ethers by dehydration of alcohol
is a bimolecular reaction (SN2) involving the Thus, benzene is activated towards
attack of an alcohol molecule on a protonated electrophilic substitution by the alkoxy group.
(ii) It can also be observed from the resonance
alcohol molecule. In the method, the alkyl group
structures that the electron density increases
should be unhindered. In case of secondary or
more at the ortho and para positions than at
tertiary alcohols, the alkyl group is hindered. As a
the meta position. As a result, the incoming
result, elimination dominates substitution. Hence,
substituents are directed to the ortho and para
in place of ethers, alkenes are formed.
positions in the benzenering.

7.28 Write the equation of the reaction of hydrogen 7.30 Write the mechanism of the reaction of HI with
iodide with: methoxy methane.
(i) 1-propoxypropane [NCERT Page-213]
(ii) method benzene and Sol. The mechanism of the reaction of HI with
(iii) benzyl ethyl ether. methoxymcthane involves the following steps:
[NCERT Page-213] Step 1: Protonation of methoxymethane:
373K
Sol. (i) C2H5CH2 − O − CH2 C2H5 ⎯⎯⎯ →
1-Propoxypropane
Step 2: Nucleophilicattackofl–:
CH3CH2CH2 − OH +CH3CH2CH2 − 1
Propan-1-ol 1-Iodopropane

(ii)
Step 3: When Hl is in excess and the reaction is
carried out at a high temperature, the methanol
formed in the second step reacts with another HI
molecule and gets converted to methyl iodide
(iii)

+
H− + CH3 OH2 → CH3 − I + H2O

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7.31 Write equations of the following reactions: Sol. The given alcohols can be synthesized by applying
(i) Friedel-Crafts reaction - alkylation of anisole. Markovnikov's rule of acid-catalyzed hydration of
(ii) Nitration of anisole. appropriate alkenes.
(iii) Bromination of anisole in ethanoic acid
medium.
(iv) Friedel-Craft’s acetylation of anisole. (i)
[NCERT Page-213]

Sol. (i)

(ii)
(ii)

(iii)

Acid-catalyzed hydration of pent-2-ene also

produces pentan-2-ol but along with pentan3-ol.
(iii)

Thus, the first reaction is preferred over the second

(iv) one to get pentan-2-ol.

(iv)

7.32 Show how would you synthesise the following 7.33 When 3-methylbutan-2-ol is treated with HBr. the
alcohols from appropriate alkenes? following reaction takes place:
CH2 − CH − CH − CH2
(i) | |
CH3 OH
(ii) Br
|
HBr
⎯⎯⎯ → CH3 − C − CH2 − CH3
|
(iii) CH3
Give a mechanism for this reaction.
(iv) (Hint: The secondary carbocation formed in step II
rearranges to a more stable tertiary carbocation by
[NCERT Page-213] a hydride ion shift from 3rd carbon atom.
[NCERT Page-213]

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Sol. The mechanism of the given reaction involves the Step 3:

following steps: Re-arrangement by the hydride-ion shift
Step 1:
Protonation

Step 2: Step 4: Nucleophilic attack

Formation of 2°carbocation by the elimination of a
water molecule

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