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.