1 Alcohols, Phenols and Ethers

EXERCISE - 1 : BASIC OBJECTIVE QUESTIONS

Introduction and Preparation of Alcohols (c) B2H6 followed by H2O2
1. Glycerine has (d) CH3CO2H/H2SO4
(a) One primary and two secondary –OH groups Ans. (c)
(b) One secondary and two primary –OH groups Sol.
CH 3  CH  CH 2  CH3 CH 2  CH 2  OH
(c) Three primary –OH groups propene 1-propanol
(d) Three secondary –OH groups Anti markovnikovs product

Ans. (b)
Given by BH 3 / H 2 O 2 / OH  only
1 C H 2  OH (electrophilic addition)
|

2CH  OH 5. Chlorination of toluene in the presence of light and heat

Sol. | followed by treatment with aqueous NaOH gives
1CH 2  OH (a) o-cresol (b) p-cresol
(c) 2, 4-dihydroxy toluene (d) Benzoic acid
Ans. (d)
2. The structural formula of cyclohexanol is
Sol.

(a) (b)

(c) (d)

Ans. (a)
Sol. Cyclohexanol-saturated cyclic alcohol - OH group directly
attached to the cyclohexane ring.

6. Which of the following reagents convert the propene to

1-propanol
3. The compound which gives the most stable carbonium ion (a) H2O, H2SO4 (b) Aqueous KOH
on dehydration is (c) MgSO4, NaBH4/H2O (d) B2H6, H2O2, OH–
Ans. (d)
(a)
Sol. Anti markovnikov product

(b)

(c)

(d)
Ans. (b)
Sol. 30 -alcohol can form  3 0 carb o ca t io n  more stable
4. Propan-1-ol can be prepared from propene by
(a) H2O/H2SO4
(b) Hg(OAc)2/H2O followed by NaBH4
Alcohols, Phenols and Ethers 2

7. Ethylene reacts with Baeyer’s reagent to give Sol.

(a) Ethane (b) Ethyl alcohol
(c) Ethylene glycol (d) None of these
Ans. (c)
Sol. Bayer’s reagent: cold. Alk. KMnO4
 gives cis diols when reacts
with alkene

11. Methanol is industrially prepared by

(a) Oxidation of CH4 by steam at 900°C
(b) Reduction of HCHO using LiAlH4
8. The product of the following reaction is (c) Reaction HCHO with a solution of NaOH
(d) Reduction of CO using H2 and ZnO–Cr2O3
Ans. (d)
Sol. a) at 900oC -extreme Temperature not favored.
(a) 2-pentanol (b) pentane b)
(c) pentan-2-one (d) 1-pentanol HCHO
Ans. (d) LiAlH 4   X  uncontrolled reactions 
Sol. Anti markovnikov’s product 
Too reactive
NaO H
c) H CH O    C H 3 O H +HC O ON a

Bi.product
ZnO/CrO3
d) CO  2H 2   CH 3OH

Hence option ‘d’ is best method.

Chemical Properties of Alcohols
9. Oxymercuration-demercuration reaction of 1-methylcyclohexene 12. Alcohols react with Grignard reagent to form
gives (a) Alkanes (b) Alkenes
(a) trans-2-methyl cyclohexanol (c) Alkynes (d) All of these
(b) cis-2-methylcyclohexanol Ans. (a)
(c) 1-methylcyclohexanol Sol. Grignard reagent with any proton
(d) mixture of cis- and trans-2-methylcyclohexanol Source  Alkane
Ans. (c)
Sol.
13. Ethylene may be obtained by dehydration of which of the
following with concentrated H2SO4 at 160–170°C
(a) C2H5OH (b) CH3OH
(c) CH3CH2CH2OH (d) (CH3)2CHCH2OH
Ans. (a)
H2SO4 (Conc)
10. 2-phenylethanol may be prepared by the reaction of CH3CH2  OH   CH 2  CH 2
170C
phenylmagnesium bromide with
(a) HCHO (b) CH3COCH3 Sol. Ethanol 
Elimination
14. Ethyl alcohol is heated with conc. H2SO4. The product formed is
(c) (d) CH3CHO
Ans. (c)
(a) (b) C2H6
(c) C2H4 (d) C2H2
Ans. (c)
 3 Alcohols, Phenols and Ethers
H2SO4 (Conc)
CH3CH2  OH   CH 2  CH 2
170C
(d) Lower members have pleasant smell and burning taste,
while higher members are odourless and tasteless
Sol. Ethanol  Ans. (c)
Elimination Sol. Lower members are soluble and solubility decreases with
increasing molecular weight.
15. Conc. H2SO4 reacts with C2H5OH at 170°C to form 20. During dehydration of alcohols to alkenes by heating with
(a) CH3COCH3 (b) CH3COOH conc. H2SO4 the initiation step is
(c) CH3CHO (d) C2H4 (a) Protonation of alcohol molecule
Ans. (d) (b) Formation of carbocation
H2SO4 (Conc) (c) Elimination of water
CH3CH2  OH   CH 2  CH 2
170C
(d) Formation of an ester
Sol. Ethanol  Ans. (a)
Elimination Sol. During Dehydration alcohols, first OH' is protonated, as
protonation makes
16. HBr reacts fastest with

(a) 2-Methylpropan-1-ol (b) 2-Methylpropan-2-ol  OH   O H 2 (good leaving group)
(c) Propan-2-ol (d) Propan-1-ol
Ans. (b) 21. Which will dehydrate most easily
(a) 3-methyl-2-butanol (b) Ethyl alcohol
Sol. 3 alcohol is more reactive in substitution reactions, as it (c) 2-methyl propane-2-ol (d) 2-methyl butan-2-ol
forms stable carbocation (3)  3  2  1 order of Ans. (c)
reactivity in substitution Sol. 3 alcohol is more reactive in dehydration as it forms 3°-
17. Isopropyl alcohol heated at 300°C with copper catalyst to carbocation (more stable) reactivity order of alcohols in
form dehydration : 3° >2° > 1°
(a) Acetone (b) Dimethyl ether
(c) Acetaldehyde (d) Ethane
Ans. (a) 22. In the following series of chemical reactions, identify Z
Sol.

(a) (b)

(c) (d)

Ans. (d)
18. Which of the following vapours passed over heated copper Sol.
to form acetone
(a)
(b)

(c)

(d)
Ans. (b)
23. What is Z in the following sequence of reactions ?
0 Cu / 300 C PCl i  Conc . H SO
Sol. 2 -alcohol ketone Z 5  X Alc
. KOH
 Y   24  Z
ii  H 2O ; boil
19. Which of the following is not characteristic of alcohols
(a) They are lighter than water (a) CH3CH2CH2OH (b) CH3CHOHCH3
(b) Their boiling points rise fairly uniformly with increasing (c) (CH3CH2)2CHOH (d) CH3CH = CH2
molecular weight Ans. (b)
(c) Lower members are insoluble in water and organic
solvents but solubility regularly increases with
molecular weight
Alcohols, Phenols and Ethers 4

Sol. Sol.

27. For the reaction,

C 2 H 5OH  HX ZnCl
2  C2 H 5X  H 2 O
the order of reactivity is
(a) HBr > HI > HCl (b) HI > HCl > HBr
(c) HI > HBr > HCl (d) HCl > HBr > HI
Ans. (c)
24. An organic compound A reacts with sodium metal and forms Sol. Order of reactivity in substitution reaction:
B. On heating with conc. H2SO4, A gives diethyl ether. A and
B are respectively HI  HBr  HCl
(a) C2H5OH and C2H5ONa 
(b) C3H7OH and C3H7ONa
(c) CH3OH and CH3ONa Strong acid,easily gives H +
(d) C4H9OH and C4H9ONa 28. The best method to prepare cyclohexene from cyclohexanol
Ans. (a) is by using
Sol. An alcohol reacts with sodium metal to form sodium alkoxide (a) Conc. HCl + ZnCl2 (b) Conc. H3PO4
and hydrogen gas. (c) HBr (d) Conc. HCl
R  OH  Na  RONa  1/ 2H 2 Ans. (b)
Sol.
 C2 H 5OH  Na  C2 H 5ONa  1/ 2H 2
A  B
Conc.H2 SO4
C2 H5 OH  C2 H5 ONa 
 C 2 H5  O  C 2 H 5
 A  B Diethyl ether

Mechanism:-

25. Which of the following will not react with NaOH In the case of a, b, and d substitution takes place.
Properties of Phenol
29. Picric acid is
(a) Trinitrotoluene (b) Trinitroaniline
(a) (c) A volatile liquid (d) 2, 4, 6-Trinitrophenol
Ans. (d)
Sol.

(b) C2H5OH
(c) CH3CONH2 (d) CH(CN)3
Ans. (b)
Sol. C2 H 5  OH  Aliphatic alcohol
 weakly acidic
NaOH  moderately basic
26. Compound ‘A’ reacts with PCl5 to give ‘B’ which on treatment
with KCN followed by hydrolysis gave propanoic acid as 2, 4, 6-Trinitrophenol (picric acid)
the product. What is ‘A’
(a) Ethane (b) Propane
(c) Ethyl chloride (d) Ethyl alcohol
Ans. (d)
 5 Alcohols, Phenols and Ethers

30. Ortho-nitrophenol is steam volatile whereas para-nitrophenol Sol.

is not. This is due to
(a) Intramolecular hydrogen bonding present in ortho-
nitrophenol
(b) Intermolecular hydrogen bonding
(c) Intramolecular hydrogen bonding present in para-
nitrophenol
(d) None of these
Ans. (a)
Sol. Intramolecular H- bonding decreases the boiling point.
31. In presence of NaOH, phenol react with CHCl 3 to form   
o-hydroxy benzaldehyde. This reaction is called Strong +M group +M (H.C) Strong-M group
(a) Riemer-Tiemann’s reaction phenoxide ion Phenoxide in phenoxide ion
(b) Sandmeyer’s reaction   
(c) Hoffmann’s degradation reaction is highly is destablized is highly stabilized
(d) Gattermann’s aldehyde synthesis destabilized
Ans. (a) 36. The correct acidic order of the following is
Sol. Conceptual
32. Phenol is less acidic than
(a) Acetic acid (b) p-nitrophenol
(c) Both (a) and (b) (d) None of these
Ans. (c)
Sol.  Carboxylic acids are more acidic than phenols.
 EWG having phenols are more acidic than phenols.
 ERG having phenols are less acidic than phenols.
33. Phenol is less acidic than
(a) Ethanol (b) Methanol (a) I > II > III (b) III > II > I
(c) o-nitrophenol (d) p-methylphenol (c) II > III > I (d) I > III > II
Ans. (c) Ans. (b)
Sol.  Carboxylic acids are more acidic than phenols. Sol.
 EWG having phenols are more acidic than phenols.
 ERG having phenols are less acidic than phenols.
34. The increasing order of acidity among phenol, p-methylphenol,
m-nitrophenol and p-nitrophenol is
(a) m-nitrophenol, p-nitrophenol, phenol, p-methylphenol
(b) p-methylphenol, m-nitrophenol, phenol, p-nitrophenol
(c) p-methylphenol, phenol, m-nitrophenol, p-nitrophenol
(d) Phenol, p-methylphenol, p-nitrophenol, m-nitrophenol
Ans. (c)   
Sol. Strong +M group +M (H.C) Strong-M group
phenoxide ion Phenoxide in phenoxide ion
  
is highly is destablized is highly stabilized
destabilized
37. Kolbe-Schmidt reaction is used for the preparation of
(a) Salicylic acid (b) Salicylaldehyde
Strong ‘M’ effect at para only-l at meta. (c) Phenol (d) Hydrocarbon
Ans. (a)
35. Increasing order of acid strength among p-methoxyphenol, Sol.
p-methylphenol and p-nitrophenol is
(a) p-Nitrophenol, p-Methoxyphenol, p-Methylphenol
(b) p-Methylphenol, p-Methoxyphenol, p-Nitrophenol
(c) p-Nitrophenol, p-Methylphenol, p-Methoxyphenol
(d) p-Methoxyphenol, p-Methylphenol, p-Nitrophenol
Ans. (d)
Alcohols, Phenols and Ethers 6

38. Benzenediazonium chloride on reaction with phenol in 40. Phenol reacts with bromine in carbon disulphate at low
weakly basic medium gives temperature to give which of the following product?
(a) Diphenyl ether (b) p-hydroxyazobenzene (a) m-bromophenol (b) o-and p-bromophenol
(c) Chlorobenzene (d) Benzene (c) p-bromophenol (d) 2,4,6-tribromophenol
Ans. (b) Ans. (b)
Sol. Sol. Phenol reacts with bromine in carbon disulphate at low
temperature to give o-and p-bromophenol.
41. The compound ‘A’ when treated with methyl alcohol and few
drops of H2SO4 gave smell of winter green. The compound
‘A’ is
(a) oxalic acid (b) tartaric acid
(c) salicylic acid (d) succinic acid
Ans. (c)
Sol.

42. With excess bromine, phenol reacts to form

(a) (b)
39.

(a)

(b) (c) (d) Mixture of (a) and (b)

(c)
Ans. (c)
Sol.

(d)

Ans. (a)
Sol.
 7 Alcohols, Phenols and Ethers

43. Which of the following is a Riemer-Tiemann reaction

(a) C 6 H 5 OH  CCl 4 NaOH
 Salicyclic acid
(b) C 6 H 5 OH  Zn 
 C 6 H 6 (a) (b)
(c) C 6 H 5 OH  NaOH 
 C 6 H 5 ONa
(d) None of these
Ans. (a)
Sol.
(c) (d)

Ans. (b)
Sol. Acetyl chloride  Acyl C
Preparation and Chemical Properties of Ethers
46. Ether is obtained from ethyl alcohol
(a) in presence of H2SO4 at 413 K
(b) in presence of H2SO4 at 474 K
(c) in presence of H2SO4 at 383 K
(d) in presence of H2SO4 at 273 K
Ans. (a)
2C2 H5  OH H
2SO 4

  C2 H5  O  C2 H 5  2 H 2 O
Sol. 140 C
413K
47. Product C in the following reaction, will be

(a) ethane (b) ethyl methyl ether

44. Which of the following reagents will produce salicylaldehyde (c) ethyl iodide (d) propane
on reaction with phenol Ans. (b)
(a) CHCl3/NaOH (b) CCl4/NaOH Aq.NaOH
(c) CH2Cl2/NaOH (d) CH3Cl/NaOH Sol. C2 H5  Br 
Substitution
 C2 H 5 OH
Ans. (b)
Sol. Riemer – Tiemann reaction  Na
CH3 I
C2 H5  O  CH3 
 C2 H 5 ONa  1/ 2H 2

48. An ether is more volatile than an alcohol having the same

molecular formula. This is due to
(a) Dipolar character of ethers
(b) Alcohols have resonating structures
(c) Inter-molecular hydrogen bonding in ethers
(d) Inter-molecular hydrogen bonding in alcohols
Ans. (d)
Sol. Intermolecular H- bonding increases B.P.
No -H- bonding in Ethers.
49. The compound which does not react with sodium is
(a) C2H5OH (b)
(c) CH3COOH (d)
Ans. (b)
Sol. There is no replaceable H+ in CH3  O  CH3 .
50. Diethyl ether is heated with one mole of HI, which is formed
(a) Ethyl alcohol and ethyl iodide
(b) Ethyl iodide only
45. In Friedal-Crafts acylation, besides AlCl3, the other reactants are (c) Ethyl alcohol only
(d) Ethyl iodide and ethane
Ans. (a)
Alcohols, Phenols and Ethers 8
Sol.
CH3 – CH2 – O – CH2 – CH3 Ans. (d)
Sol.
2
HI 1mole  SN
CH3 – CH2 – OH + I – CH2 – CH3

if HI is taken in excess, then the product is 2R – I

51. The products formed in the following reaction
are
(a)
(b)
(c)
(d) C6H6 and CH3OI
Ans. (b)
Sol. 55. In the following reaction ‘A’ is

(a) C2H5CH2CHO (b) C2H5CH2CH2OH

(c) C2H5CH2OH (d) C2H5CHO
52. On boiling with concentrated hydrobromic acid, phenyl ethyl
Ans. (b)
ether will yield
(a) Phenol and ethyl bromide Sol.
(b) Bromobenzene and ethanol
(c) Phenol and ethane
(d) Bromobenzene and ethane
Ans. (a)
Sol.

56. Which of the following product is formed, when ether is

Phenoxide ion is more stable exposed to air
53. The ether that undergoes electrophilic substitution reactions is (a) Oxide (b) Alkanes
(a) CH3OC2H5 (b) C6H5OCH3 (c) Alkenes (d) Peroxide of diethyl ether
(c) CH3OCH3 (d) C2H5OC2H5
Ans. (b) Ans. (d)
Sol. Sol.

54. What is the major product of the following reaction ?

(a) (b)

(c) (d)
 9 Alcohols, Phenols and Ethers

57. The reaction of with RMgX leads to the

formation of
(a) RCHOHR (b) RCHOHCH3
(c) R2CHCH2OH (d) RCH2CH2OH
Ans. (d)
Sol.

The compound is CH 3  CH 2  O  CH 2  CH3

Diethyl ether

Test for Alcohols and Phenol

60. Lucas test is used for
(a) Alcohols (b) Amines
 R  C2 H5  (c) Diethyl ether (d) Glacial acetic acid
58. Which of the following reaction is correctly represented Ans. (a)
Sol. ZnCl 2  Conc.HCl  Lucas reagent used to distinguish
the alcohols.
(a)
61. Lucas reagent is
(a) Conc. HCl and anhydrousZnCl 2
(b) Conc. HNO3 and hydrous ZnCl2
(c) Conc. HCl and hydrous ZnCl2
(b)
(d) Conc. HNO3 and anhydrous ZnCl2
Ans. (a)
Sol. Factual
62. The alcohol that produces turbidity immediately with
(c) ZnCl 2 + conc. HCl at room temperature
(a) 1-hydroxybutane
(b) 2-hydroxybutane
(c) 2-hydroxy-2-methylpropane
(d) (d) 1-hydroxy-2-methylpropane
Ans. (c)
Ans. (a) Sol. ZnCl 2  HCl  Lucas reagent
Sol. Reaction of 2-methoxytoluene with HBr will give It forms turbidity with 30 -alcohol immediately,as
2-methylphenol
30 alcohol forms stable carbocation  C 

59. An organic compound of molecular formula C4H10O does
not react with sodium. With excess of HI, it gives only one  From the given options
type of alkyl halide. The compound is
(a) 1-butanol (b) ethoxyethane
(c) 1-methoxypropane (d) 2-methoxypropane
Ans. (b)
Sol. 63. Victor Meyer’s test is not given by
C 4 H10 O  Alcohol ether
(a) (CH3)3COH (b) C2H5OH
  (c) (CH3)2CHOH (d) CH3CH2CH2OH
Can react Can not react Ans. (a)
with 'Na' metal with "Na"metal Sol. Victor mayer test  10  Red colour (+ve)
 it is an ether 20  Blue colour (+ve)
30  No colour (-ve)
Alcohols, Phenols and Ethers 10

64. An organic compound ‘A’ reacts with methyl magnesium Sol.

iodide, to form an addition product which on hydrolysis
forms the compound ‘B’. Compound ‘B’ gives blue colour
salt in Victor Meyer’s test. The compounds ‘A’ and ‘B’ are
respectively
(a) acetaldehyde and isopropyl alcohol
(b) acetone and isopropyl alcohol
(c) acetaldehyde and tertiary butyl alcohol
(d) acetaldehyde and ethyl alcohol
Ans. (a)
Sol. C ompound B  Victor
 M ayer' test

Mayer
 blue
 B  2° alcohol
Except formaldehyde (HCHO) all aldehydes give 2° alcohol

Molecular weight of Z(C6H14) = 6 x 12 + 14 x 1 = 86 g

mol–1
Numerical Type Questions
65. How many of the following option(s) is/are correct 67. Number of products formed during dehydration of the
match? following compounds are:
(A) CH3OH – Wood alcohol
(B) C2H5OH – Grain alcohol
(C)

Ans. 4.00
(D)
Sol.

Ans. 4.00
Sol. All four are correct match

66. Isopropyl alcohol on treatment with excess of conc. 68. The number of ether metamers represented by
H2SO4 gives ‘X’ which on treatment with HBr gives molecular formula C4H10O is
‘Y’. When ‘Y’ is dissolved in ether and treated with Ans. 3.00
sodium gives ‘Z’. Calculate the molecular weight of Sol. These are CH3CH2OCH2CH3(I),
‘Z’. CH3OCH2CH2CH2CH3(II) and CH3OCH(CH3)2(III) Here
I and II, I and III are pairs of metamers.
Ans. 86.00
 11 Alcohols, Phenols and Ethers

69. How many of the following statement(s) is/are Sol.

correct?

(A) o-phenolsulphonic acid can be converted into p-

phenolsulphonic acid in the presence of H2SO4 if
MeCOCl
temperature is increased. C8 H18O 4   Mwt 262

(B) Phenol is more acidic than benzyl alcohol Mwt = 262  178 = 84 = 2   42 

(C) Phenoxide ion activates the ring less in

comparison to phenol

(D) Bromination of phenol in aqueous medium Hence 2 OH groups are present

produces 2-bromophenol and 4-bromophenol.

73. How many of the following compound (s)
Ans. 2.00 give(s) a yellow precipitate on hypoiodite

Sol. (A) Since p-phenolsulphonic acid has more thermal oxidation?

stability than o-phenolsulphonic acid and hence 2-butanol, 1-acetyl cyclopentane, ethanol and
latter can be converted into former on heating. ethanal
Ans. 4.00
(B) Phenol is more acidic than benzyl alcohol because
Sol. Hypoiodite oxidation (NalO) or iodoform test is
phenoxide ion is more stable than benzyl alkoxide ion.
given by the organic compounds having.
70. What are the number of compounds having a benzene
nucleus can have the molecular formula C7H8O?
Ans. 5.00

Sol. Anisole, benzyl alcohol, 2-methyl phenol, 3-methyl

phenol and 4-methyl phenol.

71. Find the number of products in following reaction: 74. How many of the following test are used to
 HBr excess distinguish 1o, 2o and 3o alcohol?
Ph  O  C2 H 5  OH 

(A) Lucas test
Ans. 2.00
(B) Victor Mayer test
Sol. Br–C2H4–Br, PhOH
(C) KMnO4
72. A compound with molecular formula C8H18O4 does not
give litmus test and does not give colour with 2,4– (D) Ceric ammonium nitrate test
DNP. If the compounds reacts with excess MeCOCl, it
Ans. 3.00
gives a compound whose. vapour density is 131.
Compound A contains how many hydroxy groups? Sol. (A), (B) and (C)
Ans. 2.00
Alcohols, Phenols and Ethers 12

75. How many of the following reagents can be used to

bring out given transformation?
CH 3  CH 2  CH 2  OH  CH 3  CH 2  CHO
(i) H  / KMnO4 / 
(ii) TsCl/DMSO + NaHCO3
(iii) PCC (Pyridinium chloro chromate)
(iv) Bendict solution
(v) Red hot Cu Tube

(vi) H / K 2Cr2O7 / 
(vii) NBS / 
(viii) SeO2 / 
Ans. 4.00

Sol.
 13 Alcohols, Phenols and Ethers

EXERCISE - 2 : PREVIOUS YEAR JEE MAINS QUESTION

(a) The synthesis requires four aldol condensations between
1. The reaction of with HBr methanol and ethanol.
gives (b) The synthesis requires two aldol condensations and
two Cannizzaro reactions.
(2015) (c) The synthesis requires three aldol condensations and
one Cannizzaro reaction.
(a) (d) Alpha hydrogens of ethanol and methanol are involved
in this reaction.

(b)
Ans. (c)

(c)

Sol.
(d)

Ans. (b)
Sol. 4. The increasing order of the boiling points for the following
compounds is : Online 2017 SET( 2)
C 2 H5 OH C 2 H 5 Cl C 2 H 5 CH 3 C 2 H 5 OCH 3
(I) (II) (III) (IV)
(a) (III) < (IV) < (II) < (I) (b) (IV) < (III) < (I) < (II)
(c) (II) < (III) < (IV) < (I) (d) (III) < (II) < (I) < (IV)
Ans. (a)
Sol. B.pt order
Alcohol > alkyl halide > ether > Alkane
   
2. Phenol, when first reacts with concentrated sulphuric acid Hydrogen Polarity Small polarity non polar
and then concentrated nitric acid, gives bonding
Online 2016 SET (1)
(a) o–nitrophenol (b) p–nitrophenol
(c) Nitrobenzene (d) 2, 4,6–trinitrophenol 5. The major product formed in the following reaction
Ans. (d) is: (2017)
Sol.
OH OH
NO2
NO2
H2 SO4

HNO3


NO2
(a) (b)
3. The correct statement about the synthesis of erythritol
(C(CH2OH)4 used in the preparation of PETN is :
Online 2016 SET (2)
Alcohols, Phenols and Ethers 14

(a) (b)
(c) (d)
Ans. (a)

Sol. (c) (d)

Ans. (b)
6. Phenol on treatment with CO2 in the presence of
Sol.
NaOH followed by acidification produces compound
X as the major product. X on treatment with
(CH3CO)2O in the presence of catalytic amount of
H2SO4 produces. (2018)

(a) (b)
8. Which of the following compounds will most readily be
dehydrated to give alkene under acidic condition ?
(Online 2018 SET (3)
(a) 1-Pentanol
(b) 4-Hydroxypentan-2-one
(c) 3-Hydroxypentan-2-one
(d) 2-Hydroxycyclopentanone
Ans. (b)
(c) (d)

Sol.

Ans. (b) 9. An organic compound ‘X’ showing the following solubility

Sol. profile is: (2019-04-08/Shift-1)

7. The major product of the following reaction is :

(a) Oleic acid (b) o – Toluidine

Online 2018 SET (1) (c) Benzamide (d) m – Cresol
Ans. (d)
Sol.
 15 Alcohols, Phenols and Ethers

(A) (B)

(C) (D)

Oleic acid is also soluble in NaHCO3 Ans. (b)

o-toluidine is not soluble in NaOH as well as NaHCO3 Sol. Phenol being acidic insoluble in HCl

Benzamide is also not soluble in NaOH & NaHCO3

 m-cresol is the right answer..

10. The major product of the following reaction

Soluble in NaOH

(2019-04-08/Shift-1)

(a) (b)
Decolourises Bromine water
12. The major product of the following reaction is:

(c) (d) (2019-04-09/Shift-2)

Ans. (d)
Sol.

(a) (b)

11. The organic compound that gives following qualitative

analysis is:
Test Inference
(a) Dil. HCl Insoluble
(c) (d)
(b) NaOH solution Soluble
(c) Br2/water Decolourization
(2019-04-09/Shift-1)
Ans. (c)
Alcohols, Phenols and Ethers 16
Sol.

(a) (b)

(c) (d)

Ans. (c)
Sol.

Chloroform is used as a solvent in this reaction

13. The major product of the following reaction is: Above anion act as nucleophile for SN2 attack on
CH  C – CH 2 – Br and acetone acting as polar aprotic
solvent.

15. The products formed in the reaction of cumene with O 2

(2019-04-10/Shift-1) followed by treatment with dil. HCl are:
(2019-01-09/Shift-2)

(a) (b)
(a)

(c) (d)
(b)

Ans. (c)
Sol.
(c)

(d)

Ans. (c)
Sol.

14. What will be the major product when m-cresol is reacted

with propargyl bromide (HC  C  CH 2 Br) in presence of
K 2 CO3 in acetone (2019-04-12/Shift-2)
 17 Alcohols, Phenols and Ethers
16. The increasing order of pKa values of the following
compounds is

(c) (d)

(2019-01-10/Shift- Ans. (a)

1) Sol. SO3H will be replaced by Br this is called ipso effect.
(a) C < B < A < D (b) B < C < D < A
(c) D < A < C < B (d) B < C < A< D 19. Which of the following compounds reacts with
Ans. (d) ethylmagnesium bromide and also decolourizes bromine
Sol. Higher the Ka value lower the pKa value. water solution: (2019-01-11/Shift-2)

17. The major product of the following reaction is :

(a) (b)
(2019-01-10/Shift-2)

(c) (d)
(a) (b)

Ans. (d)
Sol. Option B and option D both will react with Grignard reagent
and decolourizes Br2 / H 2 O . (IIT has given option D only)
(c) (d)

Ans. (b)
Sol.

18. The major product of the following reactions is:

20.

(2019-01-11/Shift-1)
can not be prepared by: (2019-01-12/Shift-1)
(a) CH3 CH 2 COCH3  PhMgX
(b) PhCOCH 2 CH3  CH3 MgX
(c) PhCOCH3  CH3 CH 2 MgX
(a) (b)
(d) HCHO  PhCH(CH3 )CH 2 MgX
Ans. (d)
Sol. The reaction in option (d) will yield 1 -alcohol.
Alcohols, Phenols and Ethers 18
21. The major product of the following reaction is : Ans : (c)
Sol :

(2019-01-12/Shift-2)

23. Two compounds A and B with same molecular formula

(a) (b) (C3H6O) undergo Grignard’s reaction with methylmagnesium
bromide to give products C and D.
Products C and D show following chemical tests.

(c) (d)

C and D respectively are : (2020-09-02/Shift-2)

Ans. (b) (a)
Sol.

(b)

NaBH4 does not reduce

22. The major product of the following reaction is :

(c)

(2020-09-02/Shift-2)

(d)
(a) (b)

(c) (d) Ans : (b)

 19 Alcohols, Phenols and Ethers

Sol : Ans : (c)

Sol :

24. Consider the following reaction :

26. The major product [B] in the following reactions is:

(2020-09-04/Shift-2)
The product ‘P’ gives positive ceric ammonium nitrate
test. This is because of the presence of which of these – (a) CH3  CH2  CH  CH  CH3
OH group (s) ? (2020-09-03/Shift-2)
(a) (b) only (b) (b) and (d)
(c) (c) and (d) (d) (d) only (b)
Ans : (a)
Sol :

(c)

(d) CH2  CH2

Ans : (c)
Sol :

25. When neopentyl alcohol is heated with an acid, it slowly

converted into an 85: 15 mixture of alkenes A and B,
respectively. What are these alkenes?
(2020-09-04/Shift-1)
27. The major product of the following reaction is :

(a)
(2020-09-05/Shift-2)

(b)

(a) (b)

(c)

(c) (d)
(d)
Alcohols, Phenols and Ethers 20

Ans : (c)
30. 1-methyl ethylene oxide when treated with an excess of
Sol :
HBr produces: (2020-01-07/Shift-1)

(a) (b)

28. The increasing order of boiling points of the following (c) (d)
is :

Ans : (c)
Sol :

(2020-09-05/Shift-2)
(a) I < III < IV < II (b) III < I < II < IV
(c) I < IV < II < III (d) III < I < II < IV
Ans : (c)
Sol :

31. In the following reaction sequence, structures of A and B,

respectively will be:

(2020-01-07/Shift-2)
B.P  Hydrogen bonding

29. A solution of phenol in chloroform when treated with (a)

aqueous NaOH gives compound P as a major product. The
mass percentage of carbon in P is .......... (to the nearest
integer) (Atomic mass : C = 12; H = 1 ; O = 16)
(2020-09-06/Shift-2)
Ans : 68.85% (b)

Sol : (c)

Mass of Salicylaldehyde = 12 × 7 + 6 × 1 + 16 × 2 = 122

Mass of carbon = 12 × 7 = 84
(d)
84
The mass % of carbon   100  68.85%
122
 21 Alcohols, Phenols and Ethers

Ans : (a) Ans : (c)

Sol : Sol : In methanol, there is no resonance. In phenol, there is
resonance. In p-Ethoxyphenol, there is resonance involved
but the involvement of lone pair of oxygen in OH group is
poor as compared with phenol due to the presence of lone
pair oxygen in OCH3 group which are also involved in
resonance. So, partial double bond character develops in
C—OH bond of phenol and p-ethoxyphenol but in case of
p-ethoxyphenol, resonance is poor as compared to phenol.
So, bond length follows the order: methanol > p-
ethoxyphenol > phenol

34. Find The major product [B] of the following sequence of

reactions is: (2020-01-08/Shift-2)
32. Major product in the following reaction is:

(2020-01-08/Shift-1) (a)

(a)
(b)

(b) (c)

(d)

(c) (d) Ans : (c)

Sol :

Ans : (c)
Sol :

35. Among the following compounds A and B with molecular

formula C9H18O3, A is having higher boiling point than B.
33. Arrange the following compounds in increasing order The possible structures of A and B are:
of C—OH bond length: methanol, phenol, p-ethoxyphenol (2020-01-08-Shift-2)
(2020-01-08/Shift-1)
(a) Phenol < methanol < p-ethoxyphenol
(b) methanol < p-ethoxyphenol< phenol (a)
(c) Phenol < p-ethoxyphenol< methanol
(d) methanol < phenol < p-ethoxyphenol
Alcohols, Phenols and Ethers 22
37. Which of the following compound gives pink colour on
reaction with phthalic anhydride in conc. H2SO4 followed
by treatment with NaOH? (2021-02-24-Shift-I)
(b)

(a) (b)

(c)
(c) (d)

Ans. (d)
(d) Sol.

Ans. (b)
Sol. In option b compound A has extensive inter-molecular
hydrogen bonding because of the 3 “OH groups while in
compound B there are“OCH3 groups present and no inter-
molecular hydrogen bonding is possible.

36. What is the final product (major) ‘A’ in the given

reaction? (2021-02-24 Shift-I)

(a) (b)

38. What is ‘X’ in the given reaction?

(2021-02-25-Shift-II)

(c) (d)

CH 2 OH CH 2
Ans. (d) (a) | (b) ||
CHO CH 2
Sol.
CHO CH 2  OH
(c) | (d) ||
CHO CH 2
Ans. (b)
Sol.
 23 Alcohols, Phenols and Ethers
41. Ceric ammonium nitrate and CHCl3/alc. KOH are used for
the identification of functional groups present in _______
and _______ respectively. (2021)
(a) Alcohol, amine (b) Amine, phenol
(c) Alcohol, phenol (d) Amine, alcohol
Ans. (a)
Sol. Alcohols give the positive test with Ceric ammonium nitrate
39. Given below are two statements : (2021-02-26-Shift-I) & 1o amines give the positive test with CHCl3 + KOH i.e.
Statement I : o-Nitrophenol is steam volatile due to carbylamine test.
intramolecular hydrogen bonding.
Statement II : o-Nitrophenol has high melting due to 42. Identify A in the given reaction (2021-02-26-Shift-II)
hydrogen bonding.
In the light of the above statements, choose the most
appropriate answer from the options given below
(a) Both statement I and statement II are false
(b) Statement I is false but statement II is true
(c) Statement I is true but statement II is false
(d) Both statement I and statement II are true
Ans. (c)
Sol. Ortho nitro phenol is stream volatile due to Intramolecular
H-bonding while p-nitro phenol is less volatile due to (a) (b)
interamolecular H-bonding.p-nitro phenol has high melting
point due to more symmetric in nature.

40. Identify the major products A and B respectively in the

following reactions of phenol : (2021-02-26-Shift-I)
(c) (d)

Ans. (c)

Sol.
(a) (b)

43. Reaction of Grignard reagent, C 2H5MgBr with C8H8O

followed by hydrolysis gives compound “A” which reacts
instantly with Lucas reagent to give compound B, C10H13Cl.
(c) (d) The Compound B is: (2021-03-18-Shift-I)

Ans. (d)
Sol.
(a) (b)

(c) (d)

Ans. (c)
Alcohols, Phenols and Ethers 24
Sol. Sol.

44. Main product formed during a reaction of 1-methoxy

naphthalene with hydroiodic acid are :
(2021-03-18-Shift-II)

(a) (b)

(c) (d) 46. An organic compound A (C6H6O) gives dark green coloration
with ferric chloride. On treatment with CHCl3 and KOH,
followed by acidification gives compound B. Compound B
Ans. (b) can also be obtained from compound C on reaction with
Sol. pyridinium chlorochromate (PCC). Identify A, B and C.
(2021-07-22-Shift-II)

(a)

(b)

(c)
45. Which of the following compounds will provide a tertiary
alcohol on reaction with excess of CH3MgBr followed by
hydrolysis? (2021-07-22-Shift-II)

(d)
(a) (b)
Ans. (a)

(c) (d)

Ans. (a)
 25 Alcohols, Phenols and Ethers

Sol.

48.

(Major product)
The given reaction can occur in the presence of:
(i) Bromine water (ii) Br2 in CS2, 273 K
(iii) Br2/Fe Br3 (iv) Br2 in CHCl3, 273 K
Choose the correct answer from the options given
below: (2021-07-25-Shift-I)
(a) (ii) and (iv) only
(b) (i) and (iii) only
(c) (ii), (iii) and (iv) only
(d) (i), (ii) and (iv) only
47.
Ans. (c)
Sol.
Consider the above reaction, the major product ‘P’ is:
(2021-07-25-Shift-I)

(a) (b)

Bromine water gives tribromo derivatives while rest other

give mono bromo product in which para product is major
(c) (d) product.

Ans. (c) 49.

Sol.
Consider the above reaction, the major product "P" formed
is: (2021-07-27-Shift-II)

(a) (b)

(c) (d)

Ans. (b)
Alcohols, Phenols and Ethers 26

Sol.

Sol.

52. Which one of the following phenols does not give colour
when condensed with phthalic anhydride in presence of
conc. H2SO4? (2021-08-26-Shift-II)

(a) (b)

50.

consider the above reaction, and choose the correct

statement: (2021-07-27-Shift-II) (c) (d)
(a) The reaction is not possible in acidic medium
(b) Both compounds A and B are formed equally Ans. (b)
(c) Compound A will be the major product Sol. Only p-methylphenol does not give any colour with phthalic
(d) Compound B will be the major product anhydroxide with conc. H2SO4.
Ans. (c)
Sol. Due to steric crowding trans alkene is more stable. 53. Given below are two statements: one is labelled as:
Assertion (A) and the other is labelled as Reason (R).
Assertion (A): Synthesis of ethyl phenyl ether may be
51. The correct options for the products A and B of the
achieved by Williamson synthesis.
following reactions are: (2021-08-26-Shift-II)
Reason (R): Reaction of bromobenzene with sodium
ethoxide yields ethyl phenyl ether. In the light of the above
statements, choose the most appropriate answer from the
options given below (2021-08-27-Shift-I)
(a) Both (A) and (R) are correct and (R) is the correct
explanation of (A)
(b) (A) is correct but (R) is not correct
(a) (c) (A) is not correct but (R) is correct
(d) Both (A) and (R) are correct but (R) is NOT the correct
explanation of (A)
Ans. (b)
Sol.
(b)

(c)

(d)

Ans. (b)
 27 Alcohols, Phenols and Ethers

54. The major product of the following reaction, if it occurs by 55. To synthesize 1.0 mole of 2-methylpropan-2-ol from ethyl
SN2 mechanism is (2021-08-27-Shift-II) ethanoate ________ equivalents of CH3MgBr regent will
be required. (Integer value) (2021-07-20-Shift-I)
Ans. 2.00
Sol.

(a) (b)

(c) (d)

Ans. (d)
Sol.