Alcohols, Phenols and Ethers

1. Which one of the following can give haloform with X 2 / OH − ?

1) CH 3OH 2) CH 3CH 2CHO 3) CH 3CHO 4) CH 3CH 2CH 2OH
2. Select the incorrect option for the following reaction
CH 3CH ( OH ) CH 3
+
CH 3CH = CH 2 + H 2O ⎯⎯→
H

1) This is an example of nucleophilic addition reaction of alkenes

2) In the first step, protonation of alkene takes place to form carbocation
3) In the second step, nucleophilic attack of water takes place on carbocation
4) In the last step, deprotonation takes place to form an alcohol
3. Nitration of phenol with conc. H2SO4 followed by nitric acid gives
1)O-nitrophenol 2) meta – nitrophenol 3)P – nitrophenol 4) picric acid
4.
O − Na +

+ CH 3COCl ⎯⎯
→?

O
O O
Cl
C − OCH 3 O − C − CH 3
C − CH 3

OH

1) 2) 3) 4)
5. Which will give yellow ppt with iodine and alkali
1) Propan – 2 – ol 2) Benzophenone 3) Methylacetate 4) Acetamide
6. Which of the following when heated with KOH and primary amine gives carbylamine test
1) CHCl3 2) CH 2Cl2 3) CH 3OH 4) CCl4
7. Chloroform reacts with aniline and aqueous KOH gives:
1) Phenyl isocyanide 2) Benzene 3) Phenyl cyanide 4) none of these
8. Select the correct order of increasing boiling points of
(I) C2 H 5 − O − C2 H 5 (II) CH 3 − ( CH 2 )3 − CH 3
(III) CH 3 − ( CH 2 )2 − CH 2OH (IV) CH 3 − ( CH 2 )2 − CHO
1) I<II<III<IV 2) II<I<IV<III 3) II<I<III<IV 4) I<II<IV<III
9. In the reaction,

−OCH 3 ⎯⎯ ⎯
HBr
→P
the products are
−OH − Br − Br − Br
and CH 3 Br and CH 3OH and CH 3 Br
CH 3O −
1) 2) 3) 4)

10. The order of reactivity of hydrogen halides with ethers is

1) HI>HBr>HCl 2) HCl>HBr>HI 3) HBr>HI>HCl 4) HI>HCl>HBr
11. The major product of the following reaction is

( )
⎯⎯⎯⎯⎯⎯ →
3 1. PBr 2. KOH alc
OH

OH

OH

1) O 2) 3) O 4) O
12.

1) 2)

3) 4)
13. The best preferable reagent for the conversion of an alcohol into pure alkyl halide?
1) PCl5 2) PCl3 3) SOCl2 4) HCl / ZnCl2
14. In the cumene to phenol preparation in presence of air, the intermediate is

1) 2) 3) 4)
15. Find out the major products from the following reactions.

1) 2)

3) 4)
16. Find out the major products from the following reactions.

1) 2)

3) 4)
17.

18. Which of the following compound will produce effervescence with sodium bicarbonate?

19. Which of the following test can be used to distinguish ethanol and propan-1-ol? (
1) Lucas test (2) Ceric ammonium nitrate (3) Iodoform test (4) Ferric chloride test
20.

What is Y?
21. The compound which is most difficult to protonate is

22. Which of the following will be most readily dehydrated in acidic conditions?

23. ( CH3 )3 C − ONa + C2 H5I → X ( major ) , The compound X is

1) Isobutene 2) Di tertiary butyl ether 3) Tertiary butyl ethyl ether 4) Diethyl ether
24. Which is the best reaction for preparation of t – butyl ethyl ether ?
(1)

(2)
(3)

(4)
25.

The functional groups present in ‘X’ are

(1) (2) −OH , −COOCH 3

(3) −OCH 3 , −COOCH 3 (4)

26. Consider the following reaction
27. Which of the following alcohols react instantaneously with Lucas reagent? (NEET – 2024)

1) 2)

3) CH 3 − CH 2 − CH 2 − CH 2OH 4)
28. Major products A and B formed in the following reaction sequence, are (NEET – 2024)
OH
CH3
PBr3 alc.KOH / 
A B
( Major ) ( Major )

OH OH OH O
CH 3 Br CH3 CH 3 Br CH3
A= B= A= B=
1) 2)
Br Br
CH 3 CH 3 CH 3 CH 3

A= B= A= B=
3) 4)
29. What is the IUPAC name of the following compound.

1) 1 – phenyl – 3 – methyl but – 1 – en – 3 – ol 2) 4 – phenyl – 2 – methyl but – 3 – en – 2 – ol

3) 2 – methyl – 4 – phenyl but – 3 – en – 2 – ol 4) 1,1 – dimethyl – 3 – phenyl – but – 1 – ol
30. IUPAC name of glycerol is
1) Ethane-1,2-diol 2) Propane -1, 2, 3-triol 3) 2-Methylpropan-2-ol 4) 2-Methylpropan-1-ol
31. IUPAC name of sec – butyl alcohol is
1) Propan-2-ol 2) Butan-1-ol 3) Butan-2-ol 4) 2-Methylpropan-1-ol
32. IUPAC name of the following compound is

1) 2-Methylcyclopentanol 2) 3-Methylcyclopentanol
3) 4-Methylcyclopentanol 4) 1-Methylcyclopentanol
33. Match the column – I with column – II

Column - I Column - II
a i Catechol

b ii Hydroquinone or quinol

c iii m-Cresol

d iv Resorcinol

1) a-i,b-ii,c-iii,d-iv 2) a-iii,b-i,c-iv,d-ii 3) a-i,b-iii,c-ii,d-iv 4) a-iv,b-ii,c-iii,d-i

34. The order of C – O – H and C – O – C bond angle in methanol, phenol and methoxymethane is
1) methanol > phenol > methoxy methane 2) methoxy methane > phenol > methanol
3) Phenol > methanol > methoxymethane 4) Phenol > methoxymethane > methanol
35. The order of C – O bond length in methanol, phenol and methoxymethane is
1) methanol > methoxy methane > phenol 2) methoxy methane > phenol > methanol
3) Phenol > methanol > methoxymethane 4) Phenol > methoxymethane > methanol
36. Which of the following is not the reversible step in acid catalysed hydration of alkenes.
1) Protonation of alkene to form carbocation 2) Nucleophilic attack of water on carbocation
3) Deprotonation to form an alcohol 4) Dissociation of water molecule
37. Which of the following alkene follows Markovnikov’s rule in acid hydrolysis
1) propene 2) but – 2 – ene 3) hex – 3 – ene 4) 2,3 – dimethyl but – 2 – ene
38. Which of the following is the commercial conversion of acids in to alcohols

1) 2)
3) Both 1 & 2 4) none of these
39. Which of the following intermediate is formed from ketone after reacting with Grignard reagent.

1) 2) 3) 4) All
40. Most of the worldwide production of phenol is from
1) Cumene 2) Aniline 3) Benzene 4) Chlorobenzene
41. Match the reaction (Column – I) with its intermediate (column – II)
Reaction (Column – I) Intermediate (Column –
II)
a i

b ii

c iii

d iv

1) a-i,b-ii,c-iii,d-iv 2) a-iii,b-i,c-iv,d-ii 3) a-i,b-iii,c-ii,d-iv 4) a-iv,b-ii,c-iii,d-i

42. What is the product of the following reaction.

1) 2) 3) 4)
43. Which of the following force is responsible for the increase in boiling point of alcohols for the
given order: butan – 1 – ol < pentan – 1 – ol < hexan – 1 – ol
1) Hydrogen bond 2) Dispersion force 3) Van der waal 4) Dipole – dipole
44. The correct order of boiling point is

I) II) III)
1) I>II>III 2) II>III>I 3) II>I>III 4) III>II>I
45. Arrange the following in order of their increasing boiling points:
Pentan-1-ol, butan-1-ol, butan-2-ol, ethanol, propan-1-ol, methanol.
1) Methanol, ethanol, propan-1-ol, butan-2-ol, butan-1-ol, pentan-1-ol.
2) butan-1-ol, Pentan-1-ol, butan-2-ol, ethanol, propan-1-ol, methanol.
3) butan-2-ol, Pentan-1-ol, butan-1-ol,ethanol, propan-1-ol, methanol.
4) ethanol, Methanol, propan-1-ol, butan-2-ol, butan-1-ol, pentan-1-ol.
46. Arrange the following in order of their increasing boiling points:
Pentan-1-ol, n-butane, pentanal, ethoxyethane.
1) Pentan-1-ol, n-butane, pentanal, ethoxyethane.
2) ethoxyethane ,Pentan-1-ol, n-butane, pentanal.
3) pentanal, n-Butane, ethoxyethane and pentan-1-ol.
4) n-Butane, ethoxyethane, pentanal and pentan-1-ol.
47. Which of the following set is correct about the given processes.

I)

II)
1) Alcohol act as nucleophile in both cases 2) Alcohol act as electrophile in both cases
3) Alcohol act as nucleophile in (i) and electrophile in (ii)
4) Alcohol act as nucleophile in (ii) and electrophile in (i)
48. Assertion (A): The acid strength of alcohols decreases in the following order:
Primary > secondary > tertiary
Reason (R): An electron-releasing group (–CH3 , –C2H5 ) increases electron density on oxygen
tending to decrease the polarity of O-H bond.
1) Both assertion and reason are correct and reason is the correct explanation of assertion.
2) Both assertion and reason are correct and reason is not the correct explanation of assertion.
3) Assertion is correct, but reason is false
4) Assertion is false, but reason is correct.
49. Which of the following acidic strength is correct.
1) Alcohol > water > Phenol 2) Phenol > water > alcohol
3) Water > alcohol > Phenol 4) Phenol > alcohol > water
50. Which of the following reaction is not possible

1) 2)

3) 4)
51. Identify the incorrect statement given below.
1) an alkoxide ion is a better proton acceptor than hydroxide ion
2) water is a better proton donor (i.e., stronger acid) than alcohol.
3) Polarity of – O – H bond in alcohol is more than in phenol
4) Ionisation of both alcohol and phenol is a reversible process.
52. Statement – I: Both phenol and phenoxide has same number (five) of resonance structures.
Statement – II: Both phenol and phenoxide ion are equally stable.
1) Both statements are wrong 2) Both statements are correct
3) Only Statement I is correct 4) Only Statement II is correct
53. Which of the following compound has highest pKa value.
1) Phenol 2) Ethanol 3) p-Nitrophenol 4) o-Cresol
54. Arrange the following compounds in increasing order of their acid strength:
Propan-1-ol, 2,4,6-trinitrophenol, 3-nitrophenol, 3,5-dinitrophenol, phenol, 4-methylphenol.
1) 3,5-dinitrophenol, phenol, Propan-1-ol, 2,4,6-trinitrophenol, 3-nitrophenol, 4-methylphenol.
2) Propan-1-ol, 2,4,6-trinitrophenol, 3-nitrophenol, 3,5-dinitrophenol, phenol, 4-methylphenol.
3) Propan-1-ol, phenol, 3-nitrophenol, 4-methylphenol, 3,5-dinitrophenol, 2,4, 6-trinitrophenol.
4) Propan-1-ol, 4-methylphenol, phenol, 3-nitrophenol, 3,5-dinitrophenol, 2,4, 6-trinitrophenol.
55. Identify the correct statement among the given below.
1) phenol is million times more acidic than ethanol.
2) Phenol < m-Nitrophenol < p-Nitrophenol : pKa order
3) In alkoxide ion, the negative charge is delocalised on oxygen while in phenoxide ion, the charge
is localised.
4) The reaction of phenol with aqueous sodium hydroxide indicates that phenols are weaker acids
than alcohols and water.
56. The product in the following reaction acts as

1) Analgesic 2) Anti – inflammatory 3) Anti – pyretic 4) All of these

57. Which of the following statements are incorrect.
1) Esterification is a reversible process
2) The introduction of acetyl (CH3CO) group in alcohols or phenols is known as acetylation.
3) Acetylation of salicylic acid produces aspirin.
4) Esterification of alcohols with carboxylic acids is carried out in the presence of dilute sulphuric
acid.
58. The C – O bond in phenol is cleaved only by
1) Al 2) Zn 3) NaOH 4) K
59.

KEY
1)3 2)1 3)4 4)3 5)1 6) 1 7) 1 8) 4 9) 1 10) 1
11)3 12)2 13)3 14)4 15)1 16)1 17)2 18)3 19)3 20)3
21)3 22)3 23)3 24)2 25)1 26)2 27)2 28)3 29)3 30)2
31)3 32)1 33)2 34)2 35)1 36)3 37)1 38)2 39)3 40)1
41)2 42)2 43)3 44)3 45)1 46)4 47)3 48)1 49)2 50)4
51)3 52)3 53)2 54)4 55)1 56)4 57)4 58)2 59) 60)
61) 62) 63) 64) 65) 66) 67) 68) 69) 70)
71) 72) 73) 74) 75) 76) 77) 78) 79) 80)
81) 82) 83) 84) 85) 86) 87) 88) 89) 90)
91) 92) 93) 94) 95) 96) 97) 98) 99) 100)
12.

14.

15.

16.

26.