PHENOL

Total No.of questions in Phenol are -

Level # 1 .................................................................................... 33
Level # 2 ........................................ ......................................... 27
Level # 3 ........................................ ......................................... 17
Level # 4 ........................................ ......................................... 06

Total No. of questions .............................................................. 83

 LEVEL # 1
Questions General method of preparation Q.6 The product of the reaction of benzene with
based on
oxygen in the presence of V2O5 as catalyst
Q.1 What is the end product ‘B’ of following at 200ºC is -
sequence of reaction ? (A) Maleic anhydride (B) Benzoic acid
HNO2 H2O
(C) Phenol (D) None of these
C6H5NH2    ‘A’ 
H SO / 0ºC
 ‘B’

2 4
Q.7 Dow’s process used in the industrial
(A) C6H5N2Cl preparation of phenol, is -
(B) C6H6 NaOH
(A) C6H5Cl   C6H5OH + NaCl
(C) C6H5NH2.H2SO 4 CuCI2' 300

(D) C6H5OH 2 SiO

(B) C6H5CI+H2O   C6H5OH + HCl
425

Q.2 What are the final products of the following (C) C6H5NH2 + HNO2 
 C6H5OH + N2 +
sequence of reactions ? H2 O
(D) C6H5N2Cl +H2O  C6H5OH + N2 + HCl
C6H6 + CH3CH = CH2 Anhy . AlCl
3
   ?
Questions Structure
O / 130 ºC
2   ? 
H
 ?
based on
Catalyst

(A) Cumene and phenol Q.8 Match structures given in list I with names
given in list II and then select the correct
(B) Phenol and acetone
answer from the codes given below the lists–
(C) Cumene and acetone
(D) Benzoic acid and ethane List I List II

(A) (a) Picric ac.id

Q.3 Phenol is obtained in large scale from which
fraction of coal-tar ?
(A) Light oil fraction (B) (b) Methyl salicylate
(B) Green oil fraction
(C) Pitch
(D) Middle oil fraction (C) (c) Pyrogallol

Q.4 By which of the following reactions phenol

(D) (d) Aspirin
can be prepared industrially –
(A) Rasching process
Codes :
(B) Dow process
(A) Ad, Ba, Cb, Dc (B) Ad, Bb, Cc, Da
(C) Cumene is oxidised and the product (C) Ad, Bb, Ca, Dc (D) Ad, Bc, Cb, Da
obtained is treated with dil. H2SO 4
(D) All of the above Q.9 Benzo redical in the following is-
(A) C6H5CH2– (B) C6H4<
(C) C6H5– (D) C6H5-C 
Q.5 The compound obtained by heating
cumenehydroperoxide with dil. H2SO 4 is –
Q.10 Next higher homologue of phenol is –
(A) Phenol
(A) Hydroxy toluene
(B) Isopropyl benzene (B) Hydroxy benzene
(C) Benzene sulphonic acid (C) Dihydroxy benzene
(D) None of these (D) None of the above
Q.11 Match this list I with list II and then select Q.15 How many  electons are there in a planar
the answer from the codes given below the ring of phenol –
lists – (A) 4 (B) 6
List I List II (C) 8 (D) 10

(A) OH OH (a) p-Cresol Questions chemical properties

based on

Q.16 Match list I with II and then select the correct

(B) (b) Hydroquinone
answer from the codes given below the lists–
List I
CH2OH 
(C) (c) p-Benzoquinone (A) Phenol + NaOH + C2H5I 
OH 
(B) Phenol + NaOH +CHCI3  
(D) HO CH3 (d) Salicyl alcohol (C) Phenol + Phthalic anhydride + conc.
H2SO 4 Heat

Codes :
(A) Ab, Bc, Cd, Da (B)Ab, Bd, Ca, Dc (D) Phenol + conc. HNO 3
(C) Ab, Bc, Ca, Dd (D) Ac, Bb, Cd, Da
List II
Q.12 Which combination is mismatched – (a) Phenolphthalein
(b) Picric acid
(A) (c) Phenetole
(d) Salicylaldehyde
are..........homologues Codes :–
(A) Ac, Bd, Ca, Db (B) Ab, Bc, Ca, Dd
(B) (C) Ac, Bd, Cb, Da (D) Ac, Ba, Cd, Db

are ..............isomers Q.17 Which of the following is not a correct

statement –
(C) (A) Phenol is a much weaker acid than
benzoic acid
are............homologues (B) The reaction of ferric chloride with phenol
to give violet colour is characteristic of
C  C  Group
|
(D) OH

(C) Phenol is a stronger acid than ethanol

are.........explosives but weaker than benzyl alcohol
(D) Picric acid does not contain a -COOH
Q.13 Which of the following is not a phenolic group.
compound –
Q.18 Which of the following is a correct statement-
(A) Salol (B) o-Cresol
(A) Phenol is more acidic than ethanol
(C) Anisole (D) Quinol
(B) Phenol is less acidic than ethanol
(C) Phenol reacts with NaHCO3
Q.14 Unacceptable name f or a compound
(D) Phenol reacts with NH2OH and HCl to
containing one -OH group attached to
benzene nucleus would be- form oxime
(A) Carbolic acid (B) Hydroxybenzene
(C) Catechol (D) Phenol
Q.19 Phenol with Hinsberg’s reagent gives- Q.25 Ortho and para hydroxy acetophenone and
(A) Sulphone (B) Sulphanilic acid anhydrous AICI3 are related with the following
(C) Sulphonic ester (D) Sulphonal reaction –
(A) Phthalein reaction
Q.20 The best method for the prepration of
(B) Fries rearrangement
chlorobenzene is-
(C) Schmidt reaction
(A) + Cl2 FeCl
  3 Cl (D) Wurtz-Fittig reaction

(B) OH + PCl5  Cl Q.26 Reimer Tiemann reaction involves -

(A) Carbanion intermediate
+ POCl3 + HCl
(B) A carbene intermediate
(C) Carbonium ion intermediate
(C) + Cl2 h
 CI
(D) Free redical intermediate

(D) OH + Cl2 h

 Cl Q.27 The product obtained in the reaction,
Phenol + KOH + chloroform  product
Q.21 Which of the following reaction is called resembles with the product of the reaction –
‘Schotten-Baumann’ reaction – (A) Phenol + CO2(,HCl)
AICl3 / CH3 COCI
(A) C6H6   C6H5COCH3 (B) Phenol + HCN + HCl
(C) Phenol + CrO2Cl 2
(B) C6H5NH2  CH3 COCI
  C6H5NHCOCH3
(D) Phenol + CH3COCl
(C) C6H5OH  C
6H5 COCI
 C6H5OCOC6H5
AICI3
Q.28 The formylating agent in ‘Gattermann Koch’
(D) C6H6   C H COC H
C H COCI 6 5 6 5 synthesis is -
6 5
(A) CO + HCl (B) CO + H2
Q.22 Phenol reacts with bromine in CS2 at a low (C) HCl + HCN (D) CHCI3 + alc.KOH
temperature, the product is -
(A) m-Bromophenol Q.29 W hich of the following is not correctly
(B) p-Bromophenol matched –
(C) o-and p-Bromophenol
Heat
(D) 2, 4, 6-Tribromophenol (A) Phenol + CHCl3 + NaOH  

Q23 Phenol reacts with conc. HNO 3 in the Salicylaldehyde

presence of conc. H2SO 4 to give –
Heat
(A) Meta nitrophenol (B) Phenol + Phthalic anhydride H
SO 2 4
(B) Ortho nitrophenol
(C) Ortho and para nitrophenol Phenetole
(D) Picric acid
(C) Phenol Br2 water  Tribromophenol

Q.24 Phenol on heating with NaNO2 and a few
drops of conc. H2SO 4 gives – (D) Sodium phenate + CO2 Heat, Pr essure
 
(A) p-Nitrophenol (B) p-Nitrosophenol
(C) o-Nitrophenol (D) m-Nitrosophenol Salicylic acid
 HCl, HCN
Q.32 In Liebermann nitroso test -
Et 2 SO 4
Q.30 Phenol    (A)    (B)
NaOH AICI3 (A) Phenol reacts with nitrous acid
(B) Aniline reacts with nitrous acid
A and B in the above reaction sequence are-
(C) Phenol and aniline reacts with
NaNO2 + HCI
(D) None of the above
(A) and
Q.33 Ledrer-Mannase reaction dose not give the
following product –
(A) o-Hydroxy benzyl alcohol
(B) p-Hydroxy benzyl alcohol
(C) m-Hydroxy benzyl alcohol
(B) and
(D) (A) and (B) are correct

(C) and

(D) and

Q.31 Reaction -I :

NaOH CO 2
 Y HCl
Phenol   X 140 
C

soda lim e
Z   
 P

Reaction - II :
CCl4 soda lim e
 X HCl
Phenol NaOH  Y    Q


Wrong statement about P and Q is –

(A) Both the compounds give violet colour
with FeCl3
(B) Both the compounds on deoxygenation
give benzene
(C) Both the compounds contain phenolic -
OH group
(D) Compound P is phenol and Q is cresol
 LEVEL # 2
Q.1 When phenol is reacted with CHCl3 & NaOH Q.7 Which of the following will not be soluble in
followed by acidification, salicyladehyde is sodium carbonate solution –
obtained. Which of the following species are
involved in the above mentioned reaction as
intermediates - (A) (B)

O
H
(A) CHCl2 (B)

(C) (D)

Q.8 Under suitable conditions C6H5CH2OH (A)

(C) (D) Both (A) and (B)
C6H5OH (B), and C6H5COOH (C) can act as
acids. The increasing order of their acidic
strength is -
Q.2 The presence of -OH on adjacent carbon atoms (A) A < B < C (B) A < C < B
can be detected by the reaction of the (C) B < A < C (D) C < B < A
compound with -
(A) Conc. H2SO 4 (B) Conc. HNO3 Q.9 Kolbe’s reaction consists in obtaining –
(C) HIO4 (D) Acidic KMnO4 (A) Anisol from phenol
(B) Salicylaldehyde from phenol and CHI3
Q.3 In phenols – (C) Salicylic acid from sodium phenate and
(A) – OH group is attached in side chain CO2
(B) – OH group is directly attached to (D) Salicylic acid from phenol and CO2
benzene nucleus
Q.10 The most suitable method of separation of a
(C) Both (A) & (B) 1 : 1 mixture of o- and p- nitrophenol is –
(D) None (A) Sublimation (B) Chromatography
(C) Crystallisation (D) Distillation
Q.4 The compound containing hydrogen bond is-
(A) Toluene (B) Phenol Q.11 p-Nitrophenol is stronger acid than phenol
(C) Chlorobenzene (D) Nitrobenzene because nitro group is –
(A) Electron withdrawing
Q.5 Phenol on treatment with ammonia gives – (B) Electron donating
(A) Benzene (B) Benzoic acid (C) Basic
(C) Aniline (D) None (D) Acidic

Q.6 Salicylic acid, aspirin, nylon, plastics and Q.12 Which derivative of phenol gives effervescence
picric acid have a common raw material, with NaHCO 3 –
namely – (A) o-Cresol
(A) Methane (B) Formic acid (B) Catechol
(C) Phenol (D) Alcohol (C) 2,4,6- Trinitrophenol
(D) 2,4,6- Tribromophenol
Q.13 The product obtained by the reaction of Q.20 When phenol is treated with PCl5, the yield
phenol with benzene diazonium chloride is – of chlorobenzene is generally poor because
(A) Phenyl hydroxylamine
(B) Para amino azobenzene of the formation of -
(C) Phenyl hydrazine (A) Benzoyl chloride
(D) Para hydroxy azobenzene (B) p- Chlorophenol
Q.14 Phenol and benzoic acid can be distinguished (C) o-chlorophenol
by – (D) Triphenyl phosphate
(A) Aqueous NaHCO3 (B) Aqueous NaNO 3
(C) Aqueous NaOH (D) Conc. H2SO 4
Q.21 Idenfity the end product (B) of the following
Q.15 Phenol is converted into salicylaldehyde by– sequence of reaqction.
(A) Etard reaction OH
(B) Kolbe reaction
conc . H SO
2
(C) Reimer- Tiemann reaction    4  A Br /H O
100º C 22 B
(D) Cannizzaro reaction

Q.16 Phenol and cyclohexanol can be OH

Br Br
distinguished by using –
(A) FeCI3 (B) Na (A)
(C) PCI5 (D) CH3COCI
SO3H
Q.17 The main product of the reduction of OH
benzaldehyde with Zn-Hg/conc. HCI, is – Br Br
(A) Benzyl alcohol (B)
(B) Cyclohexyl methanol
(C) Toluene
OH
(D) None of these
SO3H
(C)
Q.18 Which of the groups will increase the acidity
of phenol –
(A) – NO 2 (B) – CN OH
(C) – X (halogens) (D) All
(D)
Q.19 (a) Main product of phenol and PCI 5 is
OH
chlorobenzene
(b) Phenol and ethanol can be distinguished Q.22 The compound which will readily couple with
by FeCI3 benzene diazonium chloride is –
(c) Phenol and benzoyl chloride reaction is (A) Benzoic acid (B) Phenol
called Schotten-Baumann reaction (C) Benzene (D) Benzaldehyde
(d) o-Cresol is the higher homologue of
Q.23 Benzyl alcohol is –
phenol
(A) CH3CH2OH (B) C6H5COCI
Of the above statements –
(C) C6H5CH2OH (D) C6H5CH2CH2OH
(A) Only a is correct
(B) b,c and d are correct
(C) a,b are correct
(D) a,c and d are correct
Q.24 In the following sequence A and B are – Q.26 Phenol is more acidic than cyclohexanol
CH2  O because –
C6H5OH    A
HCl (A) Benzene ring exists in resonance
aqNaOH
. (B) Cyclohexane ring shows resonance
C6H5OH   O - HOC6H4CH2OH
CH2  O
(C) Phenol is poor in hydrogen
SOCl2
   B (D) Cyclochexanol is rich in hydrogen
(A) The same compound (the compound o-
chloromethylphenol)
Q.27 Phenol can be converted into salicylic acid
(B) Different compounds
by heating with -
(C) Difficult to predict
(A) CO2 (under pressure) and alkali
(D) None
(B) CCl4 and alkali
(C) CHCl3 and alkali, followed by oxidation
3 NH / ZnCl
2 B
Q.25 C6H5OH   A   Benzanilide (D) all the above
300

Compound (B) in the above reaction is –

(A) Acetyl chloride (B) Benzoyl chloride
(C) Benzamide (D) Acetanilide
 LEVEL # 3
Q.1 The reaction : Q.6 When phenol (excess) is heated with PCl5,
the major product formed is -
H2O
O2N Cl + NaOH (A) chlorobenzene
heat (B) triphenyl phosphate
(C) o-chlorophenol
O2N OH + NaCl (D) p-chlorophenol

is an example of - Q.7 Consider the following sequence of reactions.

(A) nucleophilic substitution proceeding through H PO
C6H6 + CH3CH=CH2  4  A
3
addition elimination mechanism heat
(B) nucleophilic substitution proceeding through
elimination addition mechanism 1. O . heat
  2
  B + C
(C) electrophilic substitution proceeding through 2. H O  , heat
3
addition elimination mechanism The product (B) and (C) are -
(D) nucleophilic substitution proceeding through (A) benzaldehyde and acetaldehyde
SN2 mechanism (B) benzoic acid and acetic acid
(C) phenol and propionaldehyde
Q.2 Sodium benzenesulphonate is fused with solid (D) phenol and acetone
NaOH and then acidified with dilute H2SO4.
The product obtained is– Q.8 The reaction :
(A) benzene
(B) phenol
O CH2 + HI
(C) 3-hydroxybenzenesulphonic acid
(D) thiophenol
produces -
Q.3 When phenol is treated with a solution of Br2
in carbon disulphide at 0ºC, the major product (A) CH2I and I
formed is–
(A) 2, 4, 6-tribromophenol
(B) o-bromophenol (B) OH and CH2I
(C) p-bromophenol
(D) m-bromophenol
Q.4 Beznyl alcohol and phenol can be distinguished (C) OH and CH2OH
by using–
(A) FeCl3 solution (B) Na
(C) CH3COCl/pyridine (D) CH3MgI/ether (D) CH2OH and I

Q.5 Which of the following compounds undergoes

hydrolysis most readily by aqueous NaOH to Q.9 An organic compound having the molecular
furnish the corresponding phenol ? formula C8H10O on being heated with I2 and
Cl Cl dilute NaOH gives a yellow precipitate. The
compound is expected to be -
(A) C6H5CH2CH2OH
(A) (B)

(B) CH3 CH2OH

NMe2

Cl Cl
NO2 (C) H3C OH
(C) (D) CH3

NO2 NO2 (D) CHOHCH3

Each of the questions given below consist of State- Q.13 Statement I : Phenols undergo electrophilic
ment – I and Statement – II. Use the following Key substitution at the ring much more readily than
to choose the appropriate answer. aryl halides.
(A) If both Statement- I and Statement- II are Statement II: In aryl halides electron
true, and Statement - II is the correct density at the ring decreases due to resonance
explanation of Statement– I. whereas in phenols it increases.
(B) If both Statement - I and Statement - II
are true but Statement - II is not the Q.14 Statement I : —OH group in phenols cannot
correct explanation of Statement – I. be substituted easily.
(C) If Statement - I is true but Statement - II Statement II: C—O bond in phenols has
is false. partial double bond character due to resonance.
(D) If Statement - I is false but Statement - II
is true.
Q.15 Statement I : Sodium salts of phenols can
exist in water whereas sodium salts of alcohols
Q.10 Statement I : Phenol is more reactive than do not exist in water.
benzene towards electrophilic substitution.
Statement II: Phenol is stronger acid than
Statement II: In case of phenol, the water whereas alcohol is weaker acid than
intermediate carbocation is more resonance water.
stabilized.
Q.16 Statement I : Benzyl alcohol turns blue
Q.11 Statement I : p-nitrophenol is stronger acid litmus red.
than o-nitrophenol.
Statement II: Benzyl alcohol is an isomer
Statement II: Intramolecular hydrogen of p-cresol.
bonding makes ortho-isomer weaker acid than
para isomer.
Q.17 Statement I : Phenol is more reactive than
benzene towards electrophilic substitution
Q.12 Statement I : Phenol is stronger acid than reactions.
alcohols.
Statement II: In the case of phenol, the
Statement II: Phenol is stabilized by intermediate carbocation is more resonance
resonance whereas alcohols are not. stabilized.
 LEVEL # 4
(Question asked in previous AIEEE & IIT-JEE)
SECTION-A Q.3 The structure of the compound that gives a
Q.1 p–cresol reacts with chloroform in alkaline
tribromo derivative on treatment with bromine
medium to give the compound A which adds
hydrogen cyanide to form, the compound. B The water is -
latter on acidic hydrolysis gives chiral carboxylic
acid. The structure of the carboxylic acid is -
CH2OH CH3
OH
(A) (B)

(A)

CH3 CH3

(C) (D)
OH
(B) OH

Q.4 Phenol, when it first reacts with concentrated

sulphuric acid and then with concentrated nitric
(C) acid, gives -

(A) o-nitrophenol

(B) p-nitrophenol

(C) nitrobenzene
(D) (D) 2,4,6-trinitrobenzene

Q.5 The major product obtained on interaction of

phenol with sodium hydroxide and carbon
OH O–Na+
Q.2 . dioxide is -
+ CHCl3 + NaOH
CHO
(A) salicylaldehyde (B) salicyclic acid
The electrophile involved in the above reaction
(C) phthalic acid (D) benzoic acid
is -
(A) dichlorocarbene ( :CCl2)
Θ
(B) trichloromethyl anion ( CCl3 )


(C) formyl cation ( CHO )

(D) dichloromethyl cation ( CHCl 2 )
 SECTION-B
Q.1 Order of boiling point f or the following
compounds is -
OH OH
OH

OH
(I)
(II) II)
((III)

OH OH

OH IV)
((I)
III)
((IV)

(A) (I) < (II) < (III) < (IV)

(B) (I) < (II) < (IV) < (III)
(C) (IV) < (I) < (II) < (III)
(D) (II) < (I) < (III) < (IV)
 ANSWER KEY
LEVEL # 1
Q.No. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20
Ans. D B D D A C A C D A A C C B C A C A C A
Q.No. 21 22 23 24 25 26 27 28 29 30 31 32 33
Ans. C C D B B B B A B A D A C

LEVEL # 2
Q.No. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20
Ans. D C B B C C C A C D A C D A C A C D B D
Q.No. 21 22 23 24 25 26 27
Ans. A B C A B A D

LEVEL # 3
Qus. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17

Ans. A B C A D B D B D A A B C A A D A

LEVEL # 4
SECTION-A

Qus. 1 2 3 4 5
Ans. A A D A B

SECTION-B

Qus. 1
Ans. C