Alcohols, Phenols,, ether-

MCQ questions;

1. Which of the following compounds has most acidic nature?

2. Major product obtained when phenol reacts with con.H2SO4 at 280 K

(1) Salicylic acid (2) picric acid

(3) o-phenol sulphonic acid (4) p-phenol sulphonic acid

3.

The given reaction is an example for

(1) Wurtz reaction (2) Williamson reaction

(3) Kolbe reaction (4) none of the above

4. Among the alkenes which one produces tertiary butyl alcohol on acid hydration?

a) CH3CH2CH = CH2 (b) CH3CH = CH – CH2 (c) (CH3)2C = CH2 (d) CH3 − CH = CH2

5. In the Lucas test of alcohols, appearance of cloudiness is due to the formation of

a) Aldehydes (b) Ketones (c) Acid chlorides (d) Alkyl chlorides

6. Lucas reagent is
a) Anhydrous AlCl3 with concentrated HCl b) Anhydrous ZnCl2 and concentrated H2SO4
c) Anhydrous ZnCl2 and concentrated HCl d) Anhydrous CaCl2 and concentrated HCl

7. During dehydration of alcohols to alkenes by heating with concentrated 2 4 the initiation

step is
a) Protonation of alcohol molecule (b) Formation of carbocation
c) Elimination of water (d) Formation of an ester
8. In the presence of an acid catalyst, two alcohol molecules will undergo dehydration to give:
a) Ester (b) Anhydride (c) Ether (d) Unsaturated hydrocarbon

(9) Williamson’s synthesis is used for the preparation of

(a) Acid (b) Ester (c) Ether (d) Alcohol

10. For the sequence of reaction,

The compound A in the sequence is

a) 2-butanone b) Acetaldehyde c) Acetone d) Propanal

11. Which of the following reaction is /are feasible

12. The dehydration of butane-1-ol gives

(a) 1-butene as the main product (b) 2-butene as the main product
(c) Equal amounts of 1-butene and 2-butene (d) 2-methyl propene

13. The products formed in the following reaction

14.

15. Primary alcohols can be obtained from the reaction of the MgX with:
(a) HCHO (b) H2O c) CO2 (d) CH3CHO

16. Correct acidic order of the following

 (a) I > II > III (b) III > I > II (c) II > III > I (d) I > III > II

17. Which of the following reagents may be used to distinguish between phenol and benzoic acid?
(a) Aqueous NaOH (b) Tollen’s reagent (c) Molisch reagent (d) Neutral FeCl3

18. Alcohols may behave as:

(a) Bronsted acid (b) Lewis base (c) Neutral (d) All of these

19. How many isomers of C5 H11OH will be primary alcohols?

(a) 5 (b) 4 (c) 2 (d) 3

20. The reaction given below is called:

C2H5OH + SOCl2 ⟶ C2H5Cl + SO2 + HCl

(a) Kharasch effect (b) Wurtz reaction (c) Darzen’s reaction (d) Hunsdicker reaction

21. Which will not form a yellow precipitate on heating with an alkaline solution of iodine?
a) CH3CHOHCH3 (b) CH3CH2CHOHCH3 (c) CH3OH (d) CH3CH2OH

22. The major product obtained on interaction of phenol with sodium hydroxide and carbon
dioxide is
(a) Benzoic acid (b) Salicyladehyde (c) Salicylic acid (d) Phthalic acid

23. On reacting with neutral ferric chloride, phenol gives

(a) Red colour (b) Blue colour (c) Violet colour (d) Green colour

24.
25. Phenol + X → forms a tribromo derivative “X ” is

(a) Bromine in benzene (b) Bromine in water

(c) Potassium bromide solution (d) Bromine in carbon tetrachloride at 0℃

26. The characteristic group of secondary alcohol is

26. Reaction of t-butyl bromide with sodium methoxide produces:

(a) Isobutane (b) Isobutylene (c) Sodium t-butoxide (d) t-butyl methyl ether

27. Phenol can be converted to o-hydroxybenzaldehyde by

a) Kolbe’s reaction b) Reimer-Tiemann reaction c) Wurtz reaction d) Cannizaro reaction

28. Action of nitrous acid on ethyl amine gives:

a) C2H6 b) C2H5 OH c) NH3 d) nitromethane

29.

30. When phenol is treated with excess of bromine water, it gives

a) m-bromophenol (b) o-and p-bromophenols
(c) 2, 4-dibromophenol (d) 2, 4, 6-tribromophenol

31. Picric acid is

(a) 2, 4, 6-tribromophenol (b) Sym-trinitrophenol (c) trinitrophenol (d) 2, 4, 6-trinitrotoluene

32. The reaction;
is called:

a) Corey House reaction

b) Bonveault-Blanc reaction
c) Clemmensen reduction
d) None of the above

33. Increasing order of acid strength among . butanol, isopropanol and ethanol is:
a) Ethanol, isopropanol, . butanol
b) . butanol, isopropanol, ethanol
c) Isopropanol, .butanol, ethanol
d) .butanol, ethanol, isopropanol

34. Grignard reagent reacts with HCHO to produce

a) Secondary alcohol
b) Anhydride
c) Acid
d) Primary alcohol
35. The compound formed in the following sequence of reactions

a) Propyne b) Propene c) Propanal d) Propane

36. Phenol is more acidic than alcohol because

a) Phenol is more soluble in polar solvents (b) Alcohol does not lose hydrogen atom
c) Phenoxide ion is stabilised by resonance (d) Phenoxide ion doesn’t exhibit resonance

37. Which reaction will occurs?

(a) CH3CH2CH2OH b) CH3CHOHCH3 c) CH3CH2CHO d) CH3CH2OH + CH3OH

39. Which of the following does not react with sodium metal?
(a) (CH3)2O (b) CH3CH2OH (c) CH3COOH (d) C6H5OH

40. When ethyl alcohol is heated with conc.H2SO4, the product obtained is
a) CH3COOC2H5 b) C2H2 c) C2H6 (d) C2H4

41. Lucas reagent is used to distinguish among primary, secondary and tertiary:

a) Alkyl halides b) Alcohols c) Aliphatic amines d) Aromatic amines

42. Cumene process is the most important commercial method for the manufacture of phenol. Cumene is
a) 1-methyl ethyl benzene (b) Ethyl benzene (c) Vinyl benzene (d) Propyl benzene

3 The correct order of solubility of 2 and 3 alcohol in water is:

a) 3 2 (b) 2 3 (c) 3 2 (d) None of these

44. Which reagent will convert propionic acid to propanol-1?

(a) KMnO4 (b) LiAlH4 (c) Cr2O3 (d) MnO2

45. In the Liebermann test for phenols, the blue or green colour produced is due to the formation
of

46. The IUPAC name of CH3OCH(CH3)2 is:

a) 1-methoxy propane (b) 3-methoxy propane (c) Methyl-isopropylether (d) 2-methoxy propane

47. Chlorobenzene is converted into phenol in presence of NaOH at the 373 C and 300 atm. Name of the
reaction is

(a) Kolbe-Schmidt (b) Reimer-Tiemann (c) Dow (d) Friedel-Craft reaction

48. Phenol on reaction with CHCl3 and KOH give salisaldehyde. Intermediate of this reaction is
a) Carbocation b) Carbanion c) Radical (d) carbene

49. Propane, CH3— CH = CH2 can be converted into 1-propanol by oxidation. Which set of?
Reagents among the following is ideal to effect the conversion?

a) H2O (b) B2H6, H2O2 c) H2SO4 (d) None of these

50. Which of the following compounds is weakest acid?

51. Anisole is the product obtained from phenol by the reaction known as
a) Coupling b) Etherification c) Oxidation d) Esterification

52. Amongst the following, HBr reacts fastest with

a) Propane-1-ol (b) Propane-2-ol (c) 2-methyl propane-1-ol (d) 2-methyl propane-2-ol

53. Which method is employed to convert alkyl halide into alcohol?

a) Substitution (b) Addition (c) Dehydration (d) Rearrangement

54. Isopropyl alcohol and n-propyl alcohol are:

a) Position isomers (b) Chain isomers (c) Functional isomers (d) None of these

55. The general molecular formula, which represents the homologous series of alkanols is:
a) CnH2n+1O b) CnH2n+2O c) CnH2nO2 d) CnH2nO

56.

57. Phenol can be converted to o-hydroxybenzaldehyde by

a) Kolbe’s reaction b) Reimer-Tiemann reaction c) Wurtz reaction d) Cannizaro reaction

58. The reaction

a) Corey House reaction (b) Bonveault-Blanc reaction

(c) Clemmensen reduction (d) None of the above

59. Which of the following reacts fastest with a mixture of anhydrous ZnCI2 and conc. HCI?
a) Trimethyl carbinol b) Ethanol c) Propanol d) Methanol

60. In which case, methyl t-butyl ether is formed?

a) (C2H5)3CONa + CH3Cl (b) (CH3)3CONa + CH3Cl
c) (CH3)3CONa + C2H5Cl d) (CH3)2CHONa + CH3Cl

61. Structure of diethyl ether can be confirmed by:

a) Kolbe’s synthesis b) Frankland’s synthesis
(c) Wurtz’s synthesis (d) Williamson’s synthesis
62. When phenolic ether is heated with HI, it yields

63. Which of the following compound is oxidised to prepare methyl ethyl ketone?
a) 2-propanol b) 1-butanol c) 2-butanol d) Ter-butyl alcoholol

64. For the preparation ter-butylmethylether by Williamson’s method the correct choice of
reagents is:
a) Methoxide and ter-butylbromide b) Methanol and 2-bromobutane
c) 2-butanol and methylbromide d) Ter-butoxide and methylbromide

65. Dehydrogenation of 2-butanol gives:

((a) 2-butene (b) Butanone (c) Butyraldehyde (d) 1-butene

66. To prepare 2-propanol from CH3MgI, the other chemical required is:
a) HCHO b) CH3CHO c) C2H5 OH d) CO2

67. Phenol, -methylphenol, -nitrophenol and -nitrophenol follows order of increasing

strength
as
a) Phenol, -methylphenol, -nitrophenol, -nitrophenol
b) -methylphenol, pheol, -nitrophenol, -nitrophenol
c) -methylphenol, -nitrophenol, phenol, -nitrophenol
d) -nitrophenol, -nitrophenol, phenol, -methylphenol

68. Among the following, which is least acidic?

a) Phenol b) o-cresol c) p-nitrophenol d) p-chlorophenol

69. In the reaction,

The molecular formula of X is

a) C4H6O b) C4H10O c) C2H4O d) C2H6

70. When phenol is treated with zinc dust, the product formed is
(a) biphenyl (b) diphenyl ether (c) benzene (d) cyclohexanone
71. phenol, benzyl alcohol, p-methyl phenol which one is more acidic
(a) Phenol (b) Benzyl alcohol (C) p-methyl phenol (d) None of the above

72. Co2 is sent into a solution of phenol in NaOH. The product formed is

(a) Sodium phenoxide (b) Sodium benzoate

(c) Sodium Salicylate (d) Salicyaldehyde

73. Phenol is treated with with H2 in the presence of Ni. The product formed is

(a) Cyclohexanol (b) Benzyl alcohol

© Benzene (d) Cyclohexanone

74. The major product for following reaction.

75. Cyclohexanol is a:

a) Phenol b) Primary alcohol c) Sec. alcohol d) . Alcohol

76. Which reagent can distinguish C2H5OH and ϕ OH?

a) SOCl2 b) CH3COCl c) (CH3CO)2O d) CH3COOH

77.

78. Which of the following combinations can be used to synthesise ethanol?

a) CH3 MgI and CH3 COCH3 b) CH3MgI and C2H5OH
c) CH3MgI and CH3COOC2H5 d) CH3MgI and HCHO

79. Which alcohol is most acidic?

a) Methanol b) Ethanol c) Isopropyl alcohol d) t-butyl alcohol
80. Tertiary alcohol is obtained when Grignard reagent reacts with:
a) Acetone b) Butanone c) Propanone d) All of these

81. The products obtained when anisole is heated in a sealed tube with HI are

82. Phenol is soluble in water because

a) Of weak hydrogen bonding between phenol and water molecules

b) Of intermolecular hydrogen bonding between phenol molecules
c) If has a higher boiling point than that of water
d) None of the above

83. The compound CH3CH2CH2Br is converted into CH3CH2CH2OH by:

a) Dehydration b) Hydrogenation c) Elimination d) Substitution

84. Intermolecular dehydration of alcohols gives:

a) Alkenes b) Ketones c) Alkynes d) Ethers

85. Order of reactivity of halogen acids towards an alcohol is

a) HCl > HBr > HI b) HBr > HI > HCl c) HI > HBr > HCl d) HI > HCl > HBr

The decreasing order of boiling points of 2 3 alcohol is:

a) 2 3 b) 3 2 c) 2 3 d) None of these

87. By heating phenol with chloroform in alkali, it is converted into

a) Salicylic acid b) Salicyladehyde c) Anisole d) Phenyl benzoate

88. Alcohol is sometimes used in:

a) Baking powder b) Paints c) Thermometers d) Weighing

89. Benzoylation of phenol in alkaline medium is known is known as

a) Friedel-Crafts reaction b) Wurtz-Fittig reaction
c) Schotten-Baumann reaction d) None of the above.

90. Phenol gives characteristic colouration with

a) Iodine solution b) Bromine water

c) Aqueous FeCI3 solution d) Ammonium hydroxide

Assertion and reason both are correct statements and reason is correct explanation for
assertion.

(a) Both assertion and reason are true and reason is the correct explanation of assertion.
b) Assertion and reason both are correct statements but reason is not correct explanation for
assertion.
c) Assertion is correct statement but reason is wrong

d) Both assertion and reason are wrong

(91) Assertion; Phenol is more acidic than ethanol

Reason: Phenoxide ion is resonance stabilized

(92) Assertion: The major products formed by heating C6H5CH2OCH3 with HI are C6H5CH2I
and CH3OH
Reason: Benzyl cation is more stable than methyl cation.

(93) Assertion: To prepare tertiary butyl ether, ter butyl chloride and sodium ethoxide are taken.
Reason: Tertiary alkyl chloride undergoes elimination with strong alkali.

(94) Assertion: To prepare anisole-sodium phenoxide and methyl chloride are taken.
Reason: Halobenzene cannot be taken as halogen connected to benzene ring is not displaced by
nucleophile.

(95). Assertion: Ethyl methyl ether gives ethanol and methyl chloride when cleaved with HI
Reason: The reaction proceeds via SN2 mechanism.

Value Added Questions:

96. The phenol contains-OH group directly attached to carbon atom of an aromatic system
(C6H5OH). In phenols, the –OH group is attached to Sp2 hybridised carbon of an aromatic ring.
The carbon-oxygen bond length (136 pm) in phenol is slightly less than that in methanol. This is
due to (i) partial double bond charater on account of the conjugation of unshared electron pair of
oxygen with the aromatic ring and (ii) sp3 hybridised state of carbon to which oxygen is attached.

It can be prepared by various means or methods. Some important methods are alkali fusion of
sulphonates, hydrolysis of diazoiunm salts, decarboxylation of salicyclic acid and from
Griganard reagents Commerercially it is prepared from Dow’s process and from cumene. In
Dow process, phenol is obtained when chlorobenzene is heated with 6-8% NaOH at 623 K under
320 atm pressure. Aerial oxidation of cumene hdroperoxide which upon subsequent hydrolysis
with an aqueous acid gives phenol and propanone.

The following questions are multiple choice questions. Choose the most appropriate answer.

(a) Which of the following hydrocarbon is used for the world wide production of phenol?
(i) Iso- butyl benzene (ii) Iso-propyl benzene (iii) Iso-pentylbenzene
(iv) None of the above.

(b) Which of following can produce the phenol?

i) Reduction of aniline (ii) Oxidation of cholorbenzne
(iii) Oxidation of cumene (iv) acidification of cholorobenzne

© Which of the following reagent is used for the conversion of benzene sulphonic acid to phenol?

i) Calcium carbonate (ii) NaoH, HCl

(iii) Calcium hydroxide (iv) None of the above

(d) Name of product which is obtained by decarboxylation of salicylic acid with soda lime is

i) Phenol (ii) Toluene

(iii) Benzene (iv) Benzoic acid

99. Mr. Osaka was asked to prepare alcohol for acidic hydration of 1-butene. He was unaware of
fact that vessel he used had some coating of metal. In addition to alcohol (B.Pt is 373 K) and
compound X was also isolated.

(a) What is product obtained when acid hydration of 1 butene

(a) Butan-1-ol (b) butan-2-ol (c) Butane hdrate (d) none of the above

(b) What is product obtained when 1-butene treated with diborane followed by oxidation with
hydrogen peroxide.

(a) Butan-1-ol (b) butan-2-ol (c) Butane hdrate (d) none of the above

(c) which one of process follows Markonikoff addition

(a) acid hydration of 1-butene (b) hydroboration of 1-butene

© acid hydration 1-methyl cyclobut-1-ene (d) none of the above.

(d) What is major product obtained when 1-butanol dehydrated?

(a) 1- butane (b) 2- butane (c) ether (d) both (a) and (b)
 Alcohols, Phenols and ethers.

Answer Key for MCQ;

1 2 3 4 5 6 7 8 9 10

2 3 2 c d c a c c c

11 12 13 14 15 16 17 18 19 20

a b a c a b d d a c

21 22 23 24 25 26 27 28 29 30

c c c d b b b b b d

31 32 33 34 35 36 37 38 39 40

a b b d b c c a b b

41 42 43 44 45 46 47 48 49 50

b d b b a d c d b a

51 52 53 54 55 56 57 58 59 60

b d c b b a b b a b

61 62 63 64 65 66 67 68 69 70

d b c d a b b b c c

71 72 73 74 75 76 77 78 79 80

a c a c c a a d a d

81 82 83 84 85 86 87 88 89 90

a c d d c a b b c c

91 92 93 94 95 96 97

a a a a a a-ii, b-iii, c-d, d-i a-b, b-a, c-c, d-b