Alcohols, Phenols and Ethers

Class 12
MCQs Questions
1.1-Propanol and 2-propanol can be best distinguished by
(a) Oxidation with KMnO4 followed by reaction with Fehling solution
(b) Oxidation with acidic dichromate followed by reaction with Fehling solution.
(c) Oxidation by heating with copper followed by reaction with Fehling solution.
(d) Oxidation with cone. H2SO4 followed by reaction with Fehling solution.

2. The compound which gives the most stable carbonium ion on dehydration is
(a) (CH3)2CHCH2OH
(b) (CH3)3COH
(c) CH3CH2CH2CH2OH
(d) CH3CH OH CH2 CH3
3. In CH3 CH2 OH, the bond that undergoes heterolytic change most readily is
(a) C-C
(b) C-O
(c) C-H
(d) O-H

4. Phenol reacts with Br2 in CS2 at low temperature to give

(a) o-Bromophenol
(b) o-and p-promophenols
(c) p-Bromophenol
(d) 2, 4, 6Tribromophenol
5. In the reaction of phenol with CHCl3 and aqueous NaOH at 343 K, the electrophile attacking
the ring is:
(a) CHCl3
(b) CHCl2
(c) CCl2
(d) COCl2
6. Which of the following is most acidic?
(a) Phenol
(b) Benzyl alcohol
(c) m-chlorophenol
(d) cyclohexanol

7. The correct order of boiling points for primary (1°), Secondary (2°) and Tertiery (3°) alcohols is
(a) 1° > 2° > 3°
(b) 3° > 2° > 1°
(c) 2° > 1° > 3°
(d) 2° > 3° > 1°
8. When Phenol is distilled with zinc dust, it gives
(a) Benzene
(b) Toluene
(c) Benzaldehyde
(d) Benzoic acid

9. Which of the following cannot be made by using Williamson Synthesis:

(a) Methoxybenzene
(b) Benzyl p-nitrophenyl ether
(c) tert. butyl methyl ether
(d) Ditert. butyl ether

10. The I.U.P.A.C. name of the ether CH2 = CH-CH2O CH3 is

(a) Alkyl methyl ether
(b) l-Methoxy-2-propene
(c) 3-Methoxy-l-propene
(d) Vinyl dimethyl ether

11. Dehydration of alcohol to ethers is catalysed by

(a) cone. H2SO4 at 413 K
(b) Hot NaOH
(c) Hot HBr
(d) Hot HNO3

12.As the number of -OH groups in alcohol increases_____

a) boiling point decreases
b) viscosity decreases
c) density decreases
d) boiling point increases

13. tert-Butyl methyl ether on heating with HI gives a mixture of

(a) tert-Butyl alcohol and methyl iodide.
(b) tert-Butyl iodide and methanol
(c) Isobutylene and methyl iodide
(d) Isobutylene and methanol.

14. An ether is more volatile than alcohol having the same molecular formula. This is due to
(a) intermolecular hydrogen bonding in alcohols.
(b) dipolar character of ethers
(c) alcohols, having resonance structures
(d) intermolecular hydrogen bonding in ethers.

15. Cyclohexene is best prepared from cyclohexanol by which of the following:

(a) cone. H3PO4
(b) Cone. HCl/ZnCl2
(c) Cone. HCl
(d) Cone. HBr

16.Wood spirit is known as

(a) methanol
(b) ethanol
(c) acetone
(d) benzene
17. Acetone reacts with Grignard reagent to form
(a) 3° alcohol
(b) 2° alcohol
(c) ether
(d) no reaction
18. The product of acid catalysed hydration of 2-phenylpropene is
(a) 3-Phenyl-2-propanol
(b) 1-Phenyl-2-propanol
(c) 2-phenyl-2-propanol
(d) 2-phenyl-1-propanol.
19.Acid-catalysed hydration of alkenes except ethene leads to the formation of
(a) primary alcohol
(b) secondary or tertiary alcohol
(c) mixture of primary and secondary alcohols.
(d) mixture of secondary and tertiary alcohols.
20. During dehydration of alcohols to alkenes by heating with cone. H2SO4 the initial step is
(a) formation of an ester
(b) protonation of alcohol molecule
(c) formation of carbocation
(d) elimination of water
21. In the following compounds:

The order of acidity is

(a) III > IV > I > II
(b) I > IV > III > II
(c) II > I > III > IV
(d) IV > III > I > II
22. When Phenol is distilled with zinc dust, it gives
(a) Benzene
(b) Toluene
(c) Benzaldehyde
(d) Benzoic acid
23. Phenol and benzoic acid can be distinguished by_______
a) aq. NaHCO3
b) aq. NaNO3,
c) aq. NaOH
d) conc. H2SO4

24. The ether

25. The major product formed by the reaction:

(a) CH3.CHCH3.CH2OCH3
(b) CH3 CH (OCH3) CH2 CH3

26.

(a) C6H5OC2H5
(b) C2H5OC2H5
(c) C6H5OC6H5
(d) C6H5I

27.

(a) CH3CH Br CH3

(b) CH3 CH2 CH2 Br Br
(c) CH2 = CH-Br
(d) Br CH = CH-CH3

28.What happens when tertiary butyl alcohol is passed over heated copper at 300°C?
(a) Secondary butyl alcohol is formed
(b) 2-methylpropene is formed
(c) 1-butene is formed
(d) Butanol is formed
29.. A compound X with the molecular formula C3H8O can be oxidised to another compound
Y whose molecular formulae is C3H6O2. The compound X may be
(a) CH3CH2OCH3
(b) CH3CH2CHO
(c) CH3CH2CH2OH
(d) CH3CHOHCH3

30.Benzoquinone is prepared by reaction of phenol with

(a) Na2Cr2O7, H2SO4
(b) KMnO4, H2SO4
(c) Na2CrO4,HCl
(d) K2MnO4, H2SO4
31.Arrange the following alcohols in order of increasing reactivity towards sodium metal.
(i) (CH3)3C-OH
(ii) (CH3)2CH-OH
(iii) CH3CH2OH
(a) (iii) < (ii) < (i)
(b) (ii) > (i) < (iii)
(c) (i) < (ii) < (iii)
(d) (iii) < (i) < (ii)
32.. An unknown alcohol is treated with “Lucas reagent” to determine whether the alcohol is
primary, secondary or tertiary. Which alcohol reacts fastest and by what mechanism?
(a) Tertiary alcohol by SN1
(b) Secondary alcohol by SN1
(c) Tertiary alcohol by SN2
(d) Secondary alcohol by SN2
33.
Match the items of Column 1 and column 2.
Column 1 Column 2
i) Kolbe’s reaction a) Ethyl alcohol
ii) Reimer Tiemann reaction b) Alkyl halide to ether
iii)Williamsons synthesis c) Sodium Phenoxide tosalicylic acid
iv)Fermentation d) Ethylene glycol
v)Antifreeze usedin car engines e) Phenol to salicylaldehyde

34.
 Match the items of Column 1 and column 2
Column 1
Column 2
i) Ethanol to ethene a) PCC
ii) Ethene to ethanol b) tert- Butyl alcohol
iii) Oxidation of propan-1-ol with alk KMnO4. c) Picric acid
iv) Oxidation of 10 alcohol to aldehyde d) Conc. H2SO4 /1800 C
v) Phenol, Conc. HNO3 e) H2O/ H+
vi) Acetone, CH3MgBr, H2O f) Propanoic acid

Assertion and Reason Type

Note : In the following questions a statement of assertion followed by a
statement of reason is given. Choose the correct answer out of the following choices.
(i) Assertion and reason both are correct and reason is correct explanation of assertion.
(ii) Assertion and reason both are correct but reason is not correct explanation of assertion
statement.
(iii) Assertion is correct statement but reason is wrong statement.
(iv) Assertion and reason both are wrong statements.
35. Assertion : Addition reaction of water to but-1-ene in acidic medium yields butan-2-ol.
Reason : Addition of water in acidic medium proceeds through the formation of primary
carbocation.

(i) Assertion and reason both are correct and reason is correct explanation of assertion.
(ii) Assertion and reason both are correct but reason is not correct explanation of assertion
statement.
(iii) Assertion is correct statement but reason is wrong statement.
(iv) Assertion and reason both are wrong statements.

36. Assertion : p-nitrophenol is more acidic than phenol.

Reason : Nitro group helps in the stabilisation of the phenoxide ion by dispersal of
negative charge due to resonance.
(i) Assertion and reason both are correct and reason is correct explanation of assertion.
(ii) Assertion and reason both are correct but reason is not correct explanation of assertion
statement.
(iii) Assertion is correct statement but reason is wrong statement.
(iv) Assertion and reason both are wrong statements.

37. Assertion : Bond angle in ethers is slightly less than the tetrahedral angle.
Reason : There is a repulsion between the two bulky (—R) groups.
(i) Assertion and reason both are correct and reason is correct explanation of assertion.
(ii) Assertion and reason both are correct but reason is not correct explanation of assertion
statement.
(iii) Assertion is correct statement but reason is wrong statement.
(iv) Assertion and reason both are wrong statements.

38. Assertion : Boiling points of alcohols are higher than corresponding ethers.
Reason : They can form intermolecular hydrogen-bonding.
(i) Assertion and reason both are correct and reason is correct explanation of assertion.
(ii) Assertion and reason both are correct but reason is not correct explanation of assertion
statement.
(iii) Assertion is correct statement but reason is wrong statement.
(iv) Assertion and reason both are wrong statements.

39. Assertion : Like bromination of benzene, bromination of phenol is also carried out in
the presence of Lewis acid.
Reason : Lewis acid polarises the bromine molecule.
(i) Assertion and reason both are correct and reason is correct explanation of assertion.
(ii) Assertion and reason both are correct but reason is not correct explanation of assertion
statement.
(iii) Assertion is correct statement but reason is wrong statement.
(iv) Assertion and reason both are wrong statements.

40. Assertion : o-Nitrophenol has lower boiling point than p isomer.

Reason : p- Nitrophenols associated with intermolecular H bonding.
(i) Assertion and reason both are correct and reason is correct explanation of assertion.
(ii) Assertion and reason both are correct but reason is not correct explanation of assertion
statement.
(iii) Assertion is correct statement but reason is wrong statement.
(iv) Assertion and reason both are wrong statements.

41. Assertion : Ethanol is a weaker acid than phenol.

Reason : Sodium ethoxide may be prepared by the reaction of ethanol with aqueous
NaOH.
(i) Assertion and reason both are correct and reason is correct explanation of assertion.
(ii) Assertion and reason both are correct but reason is not correct explanation of assertion
statement.
(iii) Assertion is correct statement but reason is wrong statement.
(iv) Assertion and reason both are wrong statements.

42. Assertion : Phenol forms 2, 4, 6 – tribromophenol on treatment with aqueous Br2.

Reason - Phenol is ortho para directing in nature.
(i) Assertion and reason both are correct and reason is correct explanation of assertion.
(ii) Assertion and reason both are correct but reason is not correct explanation of assertion
statement.
(iii) Assertion is correct statement but reason is wrong statement.
(iv) Assertion and reason both are wrong statements.
Reason : Bromine polarises in carbon disulphide.
43. Assertion : Phenols give o- and p-nitrophenol on nitration with conc HNO3 and
H2SO4 mixture.
Reason : —OH group in phenol is o–, p– directing.
(i) Assertion and reason both are correct and reason is correct explanation of assertion.
(ii) Assertion and reason both are correct but reason is not correct explanation of assertion
statement.
(iii) Assertion is correct statement but reason is wrong statement.
(iv) Assertion and reason both are wrong statements.
44.Complete the following analogy -
Lucas reagent : A :: Bayers reagent: B
a. A- AnhydrousZnCl2 and conc HCl
B - NaOH and I2
b. A- NaOH and I2
B- AnhydrousZnCl2 and conc HCl
c. A- PCC
B - NaOH and I2
d. None of thes
45. Aspirin is obtained by acetylationof
(a)o-hydroxy benzoic acid
(b)m-hydroxy benzoic acid
(c)o-dihydroxy benzene
(d)p-dihydroxy benzene
46. The common name of Benzene-1,3-diol is
(a)Catechol
(b)Quinol
(c)Resorcinol
(d)glycerol
47. Identify Y in the following reaction
sequence

(a)Benzene
(b)Benzaldehyde
(c)Phenol
(d)None of these
48. Which of the following statements is not correct?
(a)Phenol is used to prepare analgesic drugs
(b)Solubility of phenol in water is more than that of chlorobenzene
(c)Phenol is neutralised by sodium carbonate
(d)Boiling point of o-nitrophenol is Lower than that of p-nitrophenol
49.Carbolic acid is
(a)C6H5CHO
(b)C6H6
(c)C6H5COOH
(d)C6H5OH
50. Formaldehyde reacts with which among the following to form 1-butanol
(a) Isopropylmagnesium Bromide
(b) Propylmagnesium Bromide
(c) Butylmagnesium Bromide
(d) Isobutylmagnesium Bromide