Alcohols, Phenols and Ethers

(2026)

1. At low temperature, phenol reacts with dil. HNO3 to yield

(A) 2, 4, 6-Trinitrophenol (1 Marks) (CBSE 2026-56/1/1)
(B) o-Nitrophenol only
(C) p-Nitrophenol only
(D) ortho-and para-nitrophen
2. Assertion (A) : The presence of –OH group in phenols directs the incoming
group to meta position in the ring. 1
Reason (R) : –OH group in phenols activates the aromatic ring towards
electrophilic substitution reaction.
(A) Both Assertion (A) and Reason (R) are true and Reason (R) is the correct
explanation of the Assertion (A). (1 Marks) (CBSE 2026-56/1/1)
(B) Both Assertion (A) and Reason (R) are true, but Reason (R) is not the
correct explanation of the Assertion (A).
(C) Assertion (A) is true, but Reason (R) is false.
(D) Assertion (A) is false, but Reason (R) is true.
3. Write the reaction involved in the following :
(a) Reimer-Tiemann reaction (3 Marks) (CBSE 2026-56/1/1)
(b) Kolbe’s reaction
(c) Friedal-Crafts acylation of anisole
 Answer

1. (D)
2. (D)
3.
(2025)
Q.1 Which is the correct order of acid strength from the following?
(1 Mark) (CBSE 2025 - 56/1/1)
A. H2O > C6H5OH > ROH
B. C6H5OH > H2O>ROH
C. C6H5OH>ROH>H2O
D. ROH > C6H5OH > H2O
Q.2 Assertion (A) : The boiling point of ethanol is higher than that of
methoxymethane.
Reason (R) : There is intramolecular hydrogen bonding in ethanol.
(1 Mark) (CBSE 2025 - 56/1/1)
A. Assertion (A) is true, but Reason (R) is false.
B. Assertion (A) is false, but Reason (R) is true.
C. Both Assertion (A) and Reason (R) are true, but Reason (R) is not the
correct explanation of the Assertion (A).
D. Both Assertion (A) and Reason (R) are true and Reason (R) is the correct
explanation of the Assertion (A).

Q.3 The reaction suggests that alcohols are :

(1 Mark) (CBSE 2025 - 56/7/1)
A. Basic
B. Neutral
C. Amphoteric
D. Acidic
Q.4 At low temperature, phenol reacts with Br2 in CS2 to form :
(1 Mark) (CBSE 2025 - 56/7/1)
A. p-bromophenol
B. 2,4-dibromophenol
C. o-and p-bromophenol
D. 2,4,6-tribromophenol
Q.5 Assertion (A) : A mixture of o-nitrophenol and p-nitrophenol can be
separated by steam distillation.
Reason (R) : o-nitrophenol is steam volatile due to intermolecular hydrogen
bonding.
(1 Mark) (CBSE 2025 - 56/7/1)
A. Assertion (A) is false, but Reason (R) is true.
B. Assertion (A) is true, but Reason (R) is false.
C. Both Assertion (A) and Reason (R) are true and Reason (R) is the correct
explanation of the Assertion (A).
D. Both Assertion (A) and Reason (R) are true, but Reason (R) is not the
correct explanation of the Assertion (A).
Q.6 CH3CH2OH can be converted to CH3CHO by :
(1 Mark) (CBSE 2025 - 56/5/1)
A. catalytic hydrogenation
B. treatment with PCC
C. treatment with LiAlH4
D. treatment with KMnO4
Q.7 What will be formed after oxidation reaction of secondary alcohol with
chromic anhydride (CrO3) ?
 (1 Mark) (CBSE 2025 - 56/2/1)
A. Ketone
B. Aldehyde
C. Ester
D. Carboxylic acid
Q.8 The conversion of phenol to salicylic acid can be accomplished by
(1 Mark) (CBSE 2025 - 56/2/1)
A. Reimer-Tiemann reaction
B. Friedel-Crafts reaction
C. Kolbe reaction
D. Coupling reaction
Q.9 Alkenes are formed by heating alcohols with conc. H2SO4. The first step in
the reaction is:
(1 Mark) (CBSE 2025 - 56/4/1)
A. formation of ester
B. protonation of alcohol molecule
C. elimination of water
D. formation of carbocation
Q.10 Williamson synthesis of preparing unsymmetrical ether is :
(1 Mark) (CBSE 2025 - 56/6/1)
A. SN2 reaction
B. Elimination reaction
C. SN1 reaction
D. Electrophilic addition reaction
Q.11 Assertion (A) : Phenol is strongly acidic as compared to ethanol.
Reason (R): Phenoxide ion is more stable than ethoxide ion.
(1 Mark) (CBSE 2025 - 56/6/1)
A. Assertion (A) is true, but Reason (R) is false.
B. Assertion (A) is false, but Reason (R) is true.
C. Both Assertion (A) and Reason (R) are true, but Reason (R) is not the
correct explanation of the Assertion (A).
D. Both Assertion (A) and Reason (R) are true and Reason (R) is the correct
explanation of the Assertion (A).
Q.12 Explain the mechanism of acid catalysed hydration of ethene.
(2 Mark) (CBSE 2025 - 56/5/1)
Q.13 Write the structures of the main products of the following reactions :
(2 Mark) (CBSE 2025 - 56/4/1)

Q.14 Write structure of the products of the following reactions :

(3 Mark) (CBSE 2025 - 56/7/1)
Q.15 (a) Arrange the following compounds in the increasing order of their
acidic strength :
(3 Mark) (CBSE 2025 - 56/5/1)
3,5-dinitrophenol, 4-methylphenol, phenol, 2,4,6-trinitrophenol
(b) What happens when : (write equations)
(i) Phenol is distilled with Zn dust ?
(ii) Anisole is treated with HBr ?
Q.16 (a) Can sodium ethoxide and t-butyl chloride be used for the preparation
of t-butyl ethyl ether ? Give suitable explanation. Justify your answer by
suggesting the appropriate starting material required for preparation of t-butyl
ethyl ether.
(b) Give the IUPAC name of above mentioned ether.
(3 Mark) (CBSE 2025 - 56/4/1)
Q.17 Phenols undergo electrophilic substitution reactions readily due to the
strong activating effect of OH group attached to the benzene ring. Since, the OH
group increases the electron density more to o− and p− positions therefore OH
group is ortho, para-directing. Reimer-Tiemann reaction is one of the examples
of aldehyde group being introduced on the aromatic ring of phenol, ortho to the
hydroxyl group. This is a general method used for the ortho-formylation of
phenols.
 (4 Mark) (CBSE 2025 - 56/1/1)
(a) What happens when phenol reacts with
(i) Br2/CS2
(ii) Conc. HNO3
(b) Why phenol does not undergo protonation readily?
(c) Which is a stronger acid - phenol or cresol ? Give reason.
Question 2
(c) Write the IUPAC name of the product formed in the Reimer-Tiemann
reaction.
Q.18 Alcohols undergo a number of reactions involving the cleavage of C −
OH bond. However, phenols do not undergo reactions involving the cleavage
of C − OH bond. Alcohols are weaker acids than water. Alcohols react with
halogen acids to form the corresponding haloalkanes. Phenols are stronger
acids than alcohols. A characteristic feature of phenols is that they undergo
electrophilic substitution reactions such as halogenation, nitration, etc. Since -
OH group is a strong activating group, phenol gives trisubstituted products
during halogenation, nitration, etc.
(4 Mark) (CBSE 2025 - 56/6/1)
(a) What happens when phenol is treated with the following?
(i) Br2 water
(ii) Conc. HNO3
(b) (i) Write the mechanism of alcohol reacting as nucleophile in a reaction
with CH⊕3.
Qus 2:
Alcohols undergo a number of reactions involving the cleavage of C − OH bond.
However, phenols do not undergo reactions involving the cleavage of C −
OH bond. Alcohols are weaker acids than water. Alcohols react with halogen
acids to form the corresponding haloalkanes. Phenols are stronger acids than
alcohols. A characteristic feature of phenols is that they undergo electrophilic
substitution reactions such as halogenation, nitration, etc. Since - OH group is a
strong activating group, phenol gives trisubstituted products during
halogenation, nitration, etc.
(b) (ii) Why do phenols not undergo reactions involving cleavage of C −
OH bond ?
(c) How can you distinguish between Butan-1-ol and 2-Methylpropan-2-ol by
using HCl in the presence of anhydrous ZnCl2 ?
Q.19 (a) Write chemical equations of the following reactions :
(5 Mark) (CBSE 2025 - 56/2/1)
(i) Phenol is treated with conc. HNO3
(ii) Propene is treated with B2H6 followed by oxidation by H2O2/OH−.
(iii) Sodium t-butoxide is treated with CH3Cl.
(b) Give a simple chemical test to distinguish between butan-1-ol and butan-2-
ol.
(c) Arrange the following in increasing order of acid strength : phenol, ethanol,
water

Answer
Q.1 B
Q.2 A
Q.3 D
Q.4 C
Q.5 B
Q.6 B
Q.7 A
Q.8 C
Q.9 B
Q.10 A
Q.11 D
Q.12 The mechanism of the reaction involves the following three steps:
Step 1: Protonation of alkene to form carbocation by electrophilic
attack of H3O+.

Q.13
Q.14

Q.15
(a) 4-methylphenol < Phenol < 3,5-dinitrophenol < 2,4,6-trinitrophenol
(b)
(i)
(ii)

Q.16 (a) No
Sodium ethoxide is a strong nucleophile as well as a strong base so elimination
reaction of tbutyl chloride predominates over substitution.
Chloroethane and [Link]-butoxide /C2H5Cl and (CH3)3CONa
(b)2-Ethoxy-2-methylpropane
Q.17
/ 2,4,6-Trinitrophenol / Picric acid is formed.
(b) Due to resonance, the lone pair of electrons on oxygen is not easily
available for protonation.
(c) Phenol
Due to electron releasing effect (+ l effect) of methyl group/ phenoxide ion
formed is less stable in cresol.

Qus 2: Solution: (c) 2-Hydroxybenzaldehyde / 2-

Hydroxybenzenecarbaldehyde.
Q.18

Qus 2 (b) (ii) due to sp2 hybridisation leading to shorter bond length / Due to
resonance leading to partial double bond character of C-OH bond
(c) 2-Methylpropan-2-ol gives turbidity immediately whereas butan-1-ol does
not react.
Q.19

(b) On heating with NaOH + I, Butan-2-ol gives yellow ppt. Of

iodoform (CHI3) whereas Butan-1ol does not.
(Or any other suitable chemical test)
(c) Ethanol < Water < Phenol.

2024
Q.1 Out of the following alkenes, the one which will produce tertiary butyl
alcohol on acid catalysed hydration is
(1 Mark) (CBSE 2024 - 56/5/1)
A. CH3CH = CH2
B. CH3CH2CH = CH
C. CH3 – CH = CH − CH3
D. (CH3)2C = CH2
Q.2 Which of the following species can act as the strongest base?
(1 Mark) (CBSE 2024 - 56/5/1)
A. OH−
B. RO−
C.

D. C6H5O−
Q.3 Assertion (A) : p-methoxyphenol is a stronger acid than p-nitrophenol.
Reason (R) : Methoxy group shows +I effect whereas nitro group shows -I
effect.
(1 Mark) (CBSE 2024 - 56/5/1)
A. Both Assertion (A) and Reason (R) are true and Reason (R) is the correct
explanation of the Assertion (A).
B. Both Assertion (A) and Reason (R) are true, but Reason (R) is not the
correct explanation of the Assertion (A).
C. Assertion (A) is false, but Reason (R) is true.
D. Assertion (A) is true, but Reason (R) is false.
Q.4 Which of the following compounds will give a ketone on oxidation with
chromic anhydride (CrO3) ?
(1 Mark) (CBSE 2024 - 56/1/1)
A. CH3CH2CH2OH
B.

C. (CH3)2CH − CH2OH
D. (CH3)3C – OH
Q.5 The reaction of an alkyl halide with sodium alkoxide forming ether is known
as :
(1 Mark) (CBSE 2024 - 56/1/1)
A. Wurtz reaction
B. Reimer-Tiemann reaction
C. Williamson synthesis
D. Kolbe reaction
Q.6 The correct order of the ease of dehydration of the following alcohols by the
action of conc. H2SO4 is :
(1 Mark) (CBSE 2024 - 56/1/1)

Q.7 Which one of the following compounds has the lowest pKa value ?
(1 Mark) (CBSE 2024 - 56/3/1)
A. p-Cresol
B. p-Nitrophenol
C. 2,4,6-Trinitrophenol
D. m-Nitrophenol
Q.8 (CH3)2CH – O − CH3 when treated with HI gives :
(1 Mark) (CBSE 2024 - 56/3/1)
A. (CH3)2CH – I + CH3 − I
B. (CH3)2CH – OH + CH3 − I
C. (CH3)2CH – OH + CH3OH
D. (CH3)2CH – I + CH3OH
Q.9 Assertion (A) : The boiling point of ethanol is higher than that of dimethyl
ether.
Reason (R) : Ethanol molecules are associated through hydrogen bonding
whereas in dimethyl ether, it is not possible.
(1 Mark) (CBSE 2024 - 56/3/1)
A. Both Assertion (A) and Reason (R) are true, but Reason (R) is not the
correct explanation of the Assertion (A).
B. Assertion (A) is true, but Reason (R) is false.
C. Assertion (A) is false, but Reason (R) is true.
D. Both Assertion (A) and Reason (R) are true and Reason (R) is the correct
explanation of the Assertion (A).
Q.10 Nucleophilic addition of Grignard reagent to ketones followed by
hydrolysis with dilute acids forms :
(1 Mark) (CBSE 2024 - 56/4/1)
A. Secondary alcohol
B. Tertiary alcohol
C. Primary alcohol
D. Alkene
Q.11 Match the reagents required for the given reactions :
(1 Mark) (CBSE 2024 - 56/4/1)

A. I − (q), II − (r), III − (p), IV − (s)

B. I − (p), II − (s), III − (r), IV − (q)
C. I − (r), II − (p), III − (s), IV − (q)
D. I − (s), II − (q), III − (p), IV − (r)
Q.12 Assertion (A) : p-nitrophenol is less acidic than phenol.
Reason (R) : Nitro group is electron withdrawing and helps in the stabilisation
of p-nitrophenoxide ion.
(1 Mark) (CBSE 2024 - 56/4/1)
A. Assertion (A) is false, but Reason (R) is true.
B. Assertion (A) is true, but Reason (R) is false.
C. Both Assertion (A) and Reason (R) are true and Reason (R) is the correct
explanation of the Assertion (A).
D. Both Assertion (A) and Reason (R) are true, but Reason (R) is not the
correct explanation of the Assertion (A).
Q.13 Which of the following is most acidic?
(1 Mark) (CBSE 2024 - 56/2/1)
A.

B.

C.

D.

Q.14 Anisole reacts with HI to give :

(1 Mark) (CBSE 2024 - 56/2/1)
A.

B.

C.
D.

Q.15 Ethanol on heating with conc. H2SO4 at 413 K gives :

(1 Mark) (CBSE 2024 - 56/2/1)
A. CH2 = CH2
B. C2H5 – O − C2H5
C. C2H5OSO3H
D. C2H5 – O − CH3
Q.16 Give the structure of the major product expected from the following
reactions :
(3 Mark) (CBSE 2024 - 56/5/1)
(a) Reaction of Ethanal with methyl-magnesium bromide followed by
hydrolysis.
(b) Hydration of But-1-ene in the presence of dilute sulphuric acid.
(c) Reaction of phenol with bromine water.
Q.17

(3 Mark) (CBSE 2024 - 56/1/1)

Q.18 Compound (A) (C6H12O2) on reduction with LiAlH4 gives two compounds
(B) and (C). The compound (B) on oxidation with PCC gives compound (D)
which upon treatment with dilute NaOH and subsequent heating gives
compound (E). Compound (E) on catalytic hydrogenation gives compound (C).
The compound (D) is oxidized further to give compound (F) which is found to
be a monobasic acid (Molecular weight = 60). Identify the compounds (A), (B),
(C), (D), (E) and (F).
(3 Mark) (CBSE 2024 - 56/1/1)
Q.19 (a) Write the equations of the reactions involved in the following:
(3 Mark) (CBSE 2024 - 56/3/1)
(i) Reimer-Tiemann reaction
(ii) Kolbe's reaction
(b) Name the reagent used in the bromination of phenol to form 2,4,6-
Tribromophenol.
Q.20 Write chemical equations for the following reactions : (Do any three)
(3 Mark) (CBSE 2024 - 56/4/1)
(a) Hydroboration-oxidation reaction
(b) Williamson Synthesis
(c) Friedel-Crafts Alkylation of Anisole
(d) Reimer-Tiemann Reaction
Q.21 Give the equations of reactions for the preparation of : (any three)
(3 Mark) (CBSE 2024 - 56/2/1)
(a) Phenol from chlorobenzene
(b) Salicylaldehyde from phenol
(c) 2-Methoxyacetophenone from anisole
(d) Picric acid from phenol

Answer
Q.1 D
Q.2 B
Q.3 C
Q.4 B
Q.5 C
Q.6 A
Q.7 C
Q.8 B
Q.9 D
Q.10 B
Q.11 C
Q.12 A
Q.13 C
Q.14 C
Q.15 A
Q.16
Q.17 (a)

(b) (i) CH3 − CH2 − CH2 − CH2 – OH

(ii)
Q.18

Q.19

Q.20
Q.21