NCERT LINE BY LINE CHEMISTRY- 9163681973

UNIT

8 ALCOHOLS, PHENOLS AND ETHERS

Exercise 1: NCERT Based Topic-wise MCQs

8.0 INTRDUCTION
1. In benzyl alcohol, −OH group directly attach to NCERT Page-324/ N-194
(a) 𝑠𝑝3 hybridised carbon (b) 𝑠𝑝2 hybridised carbon
(c) 𝑠𝑝 hybridised carbon
(d) None of these

8.1 CLASSIFICATION
2. Which of the following shows structure of allylic alcohol? NCERT Page-324/N-194
(i) CH2 = CH − CH2 OH
(ii) CH2 = CH − OH
(iii) CH2 = CH − CH(CH3 )OH
(iv) CH2 = CH − C(CH3 )2 OH
(a) (i), (iii) and (iv)
(b) (i), (ii) and (iv)
(c) (ii), (iii) and (iv)
(d) (i), (ii), (iii) and (iv)
3. Which of the following is aliphatic dihydric alcohol? NCERT Page-325/ N-195
(a) Glycerol (b) Ethylene glycol (c) Catechol (d) Resorcinol
4. An example of a compound with functional group-O-is: NCERT Page N-198
(a) acetic acid
(b) methylalcohol
(c) diethyl ether
(d) acetone
5. In which of the following structures hydroxyl group is attached to 𝑠𝑝2 carbon atom? NCERT Page-325/N-195
(a) (b)

(C) (d)
6. Identify the secondary alcohols from the following set: (i) CH3 CH2 CH(OH)CH3 NCERT-N-194, CBSE Paper 2021-22
(i) CH3 − CH2 − 𝐶𝐻(𝑂𝐻) − CH3 (ii) (C2 H5 )3 COH
(iii) (d)

(a) (i) and (iv)

(c) (i) and (ii)
(b) (i) and (iii)
(d) (i), (iii) and (iv)

8.2 NOMENCLATURE
7. The IUPAC name of below compound is NCERT Page-325 & 326/N-197

(a) 1,1-dimethyl-1,3-butanediol
(b) 2-methyl-2,4-pentanediol
(c) 4-methyl-2,4-pentanediol
(d) 1,3,3-trimethyl-1, 3-propanediol
8. Butane-2-ol is NCERT Page-329/N-194
(a) primary alcohol
(b) secondary alcohol
(c) tertiary alcohol
(d) aldehyde
9. Cresol has NCERT Page-327/N-197
(a) Alcoholic-OH
(c) −COOH
(b) Phenolic- OH
(d) −CHO
10. Vinyl Carbonyl is NCERT Page-N-197
(a) HO − CH2 − CH = CH2
(b) CH3 C(OH) = CH2
(c) CH3 − CH = CH − OH
(d) CH3 − C(CH2 OH) = CH2

8.3 STRUCTURE OF FUNCTIONAL GROUP

11. The C − O − C angle in ether is about NCERT Page-329/N-198
(a) 180∘
(b) 190∘ 28′
(c) 110∘
(d) 105∘
12. The C − O − H bond angle in alcolols is slightly less than the tetrahedral angle whereas the C − O − C bond angle in
ether is slightly greater because NCERT Page-329/N-198 & 199
(a) of repulsion between the two bulky R groups.
 (b) O atom in both alcohols and ethers is 𝑠𝑝3 -hybridised.
(c) lone pair - lone pair repulsion is greater than bond pair - bond pair repulsion
(d) None of these.

8.4 ALCOHOLS AND PHENOLS

13. Which is the most suitable reagent for the following transformation?

(a) Tollen's reagent

(c) CrO2 Cl2 /CS2
(b) I2 NaOH
(d) alkaline KMnO4
14. Acid catalyzed hydration of alkenes except ethene leads to the formation of NCERT Page-329/N-199
(a) primary alcohol
(b) secondary or tertiary alcohol
(c) mixture of primary and secondary alcohols
(d) mixture of secondary and tertiary alcohols
15. Ethyl alcohol can be prepared from Grignard reagent by the reaction of: NCERT Page-N-201
(a) HCHO
(b) R 2 CO
(c) RCN
(d) RCOCl
16. Isopropyl alcohol is obtained by reacting which of the following alkenes with concentrated H2 SO4 followed by boiling
with H2 O ? NCERT Page-329/N-199
(a) Ethylene
(b) Propylene
(c) 2-Methylpropene
(d) Isoprene
17. Which of the following reacts with NaOH to give an alcohol?
(a) Propene
(b) Butene
(c) Ethanal
(d) Methanal
18. Commercially carboxylic acids are reduced to alcohols by converting them to the____ NCERT Page-330/N-200
(a) esters
(c) ketones
(b) aldehydes
(d) amines
19. The gas evolved on heating CH3 MgBr in methanol is :
(a) Methane
(b) Ethane
(c) Propane
(d) HBr
20. Alcohols of low molecular weight are NCERT Page-333/N-204
(a) soluble in water
(b) soluble in water on heating
 (c) insoluble in water
(d) insoluble in all solvents
21. Which of the following has lowest boiling point? NCERT Page-N 203
(a) 𝑝-Nitrophenol
(b) 𝑚-Nitrophenol
(c) 𝑜-Nitrophenol
(d) Phenol
22. In the following reaction : NCERT Page-N 202

The compounds A and B respectively are:

(a) (b)

(C) (d)

23.
[A] will show NCERT PAGE- 340/210
(a) Br2 water test (b) Tollen's test (c) Victor maeyer test (d) Lucas test
24. Phenol does not undergo nucleophilic substitution reaction easily due to: [CBSE Sample Paper 2021-2022]
(a) acidic nature of phenol NCERT Page-341/N-206 & 207
(b) partial double bond character of C − OH bond
(c) partial double bond character of C − C bond
(d) instability of phenoxide ion
25. CH3 CH2 CH2 CH2 OH + NaBr + H ⊕ ⟶
Identify product and mechanism of the reaction NCERT Page-N-208
(a) (b)
(C) (d)

26. Which one of the following compounds has the most acidic nature? NCERT Page-337/N-206
(a) (b)

(C) (d)
27. Which of the following compounds is oxidised to prepare methyl ethyl ketone? NCERT Page-N-210
(a) 2-Propanol
(b) 1-Butanol
(c) 2-Butanol
(d) t-Butyl alcohol
28. The compound which reacts fastest with Lucas reagent at room temperature is NCERT PAGE-338/N-208
(a) butan-1-ol
(b) butan-2-ol
(c) 2-methyl propan-1-ol
(d) 2-methylpropan-2-ol
29. When phenol is treated with excess bromine water, it gives: NCERT Page-342/N-212
(a) 𝑚-bromophenol
(c) 2,4-dibromophenol
(b) 𝑜 - and 𝑝-bromophenol
(d) 2, 4, 6-tribromophenol
30. A compound ' 𝑋 ' is acidic and it is soluble in NaOH solution, but insoluble in NaHCO3 solution. Compound ' X ' also
gives violet colour with neutral FeCI3 solution. The compound ' X ' is :
(a) (b)

(C) (d)

31. Ethyl alcohol exhibits acidic character on reacting it with NCERT Page-335/N-205
(a) acetic acid
(b) sodium metal
(c) hydrogen chloride
(d) acidic K 2 Cr2 O7
32. Phenol, when first reacts with concentrated sulphuric acid and then with concentrated nitric acid, it gives
(a) 2,4, 6-trinitrophenol NCERT Page-341/N-211
(b) 𝑜-nitrophenol
(c) 𝑝-nitrophenol
(d) nitrobenzene

33. cannot be prepared by:

(a) CH3 CH2 COCH3 + PhMgX NCERT Page-N-201
(b) PhCOCH2 CH3 + CH3 MgX
(c) PhCOCH3 + CH3 CH2 MgX
(d) HCHO + PhCH(CH3 )CH2 MgX
34. Propene, CH3 CH = CH2 can be converted into 1-propanol by oxidation. Indicate which set of reagents amongst the
following is ideal to effect the above conversion? NCERT Page-330/N-200
(a) KMnO4 (alkaline)
(b) Osmium tetraoxide (OsO4 /CH2 Cl2 )
(c) B2 H6 and alk. H2 O2
(d) O3 /Zn
 X
35. C6 H5 − CH = CHCHO → C6 H5 CH = CHCH2 OH. In the above sequence, X can be NCERT Page − 330/N − 200
(a) N2 /Ni
(b) NaBH4
(c) K 2 Cr2 O7 /H +
(d) Both (a) and (b)
36. Consider the following reaction: NCERT Page-343/N-213
Zn dust CH3 Cl Alk. KMnO4
Phenol → X → Y → Z
Anhydrous AlCl3
The product 𝑍 is
(a) benzaldehyde
(b) benzoic acid
(c) benzene
(d) toluene
37. Decreasing order of acid strength of different OH groups is NCERT Page-335/N-205

(a) 1 > 2 > 3 > 4

(b) 1 > 3 > 4 > 2
(c) 1 > 4 > 3 > 2
(d) 4 > 3 > 1 > 2
38. The alcohol which does not give a stable compound on dehydration is NCERT Page-339/N-208
(a) ethyl alcohol
(b) methyl alcohol
(c) 𝑛-Propyl alcohol
(d) 𝑛-Butyl alcohol
39. A compound of the formula C4 H10 O reacts with sodium and undergoes oxidation to give a carbonyl compound which
does not reduce Tollen's reagent, the original compound is NCERT Page-N-205
(a) Diethyl ether
(b) 𝑛-Butyl alcohol
(c) Isobutyl alcohol
(d) sec-Butyl alcohol
𝐏+𝐈𝟐 𝐌𝐠 𝐇𝐂𝐇𝐎 𝐇𝟐 𝐎
40. In the following sequence of reactions, 𝐂𝐇𝟑 𝐂𝐇𝟐 𝐎𝐇 → 𝐀 → 𝐁 → 𝐂 → 𝐃
ether
The compound D is NCERT Page-331/N-201
(a) propanal
(c) 𝑛-butyl alcohol
(b) butanal
(d) 𝑛-propyl àlcohol.
41. The major product formed in the following reaction is :
 (a) (b)

(C) (d)

42.
Reagent R is NCERT PAGE 330/N-200
(a) NaBH4 / Ether /H ⊕
(c) B2 H6 /H2 O
(b) LiAlH4 / Ether /H ⊕
(d) Red⁡ P/HI (b)

43.
Major product is NCERT Page-339/N-209
(a) (b)

(C) (d)

8.5 COMMERCIALLY IMPORTANT ALCOHOLS

44. Which enzyme converts glucose and fructose both into ethanol? NCERT Page-344/N-214
(a) Diastase
(b) Invertase
(c) Zymase
(d) Maltase
45. An industrial method of preparation of methanol is : NCERT Page-344/N-214
(a) catalytic reduction of carbon monoxide in presence of ZnO − Cr2 O3
(b) byreacting methane with steam at 900∘ C with a nickel catalyst
(c) by reducing formaldehyde with lithium aluminium hydride
(d) by reacting formaldehyde with aqueous sodium hydroxide solution
46. 'Drinking alcohol' is very harmful and it ruins the health. 'Drinking alcohol' stands for NCERT Page-344/N-214
(a) drinking methyl alcohol (b) drinking ethyl alcohol
(c) drinking propyl alcohol (d) drinking isopropyl alcohol
47. In the commercial manufacture of ethyl alcohol from starchy substances by fermentation method. Which enzymes
stepwise complete the fermentation reaction NCERT Page-344/N-214
(a) Diastase, maltase and zymase (b) Maltase, zymase and invertase
(c) Diastase, zymase and lactase (d) Diastase, invertase and zymase
48. Select the incorrect statement about the fermentation. NCERT Page-344/N-214
 a) When grapes are crushed, sugar and the enzyme come in contact and fermentation starts
b) Fermentation takes place in anaerobic conditions
c) Carbon monoxide is released during fermentation
d) If air gets into fermentation mixture, the oxygen of air oxidises ethanol to ethanoic acid which in turn destroys the
taste of alcoholic drinks
49. Denaturation of alcohol is the [NCERT(Page-344/N-214
a) mixing of CuSO4 (a foul smelling solid) and pyridine (to give the colour) to make the commercial alcohol unfit for
drinking
b) mixing of CuSO4 (to give the colour) and pyridine (a foul smelling solid) to make the commercial alcohol unfit for
drinking
c) mixing of Cu(OAc)2 and ammonia to make the commercial alcohol unfit for drinking
d) mixing of Cu(OAc)2 and pyridine to make the commercial alcohol unfit for drinking.

8.6 ETHERS
50. Which of the following cannot be made by using Williamson's synthesis? NCERT Page-340 & 345/N-215
(a) Methoxybenzene
(b) Benzyl 𝑝-nitrophenyl ether
(c) Methyl tertiary butyl ether
(d) Di-tert-butyl ether
51. Ethanol and dimethyl ether form a pair of functional isomers. The boiling point of ethanol is higher than that of
dimethyl ether, due to the presence of NCERT Page-334/N-204
(a) H-bonding in ethanol
(b) H-bonding in dimethyl ether
(c) CH3 group in ethanol
(d) CH3 group in dimethyl ether
52. An ether is more volatile than an alcohol having the same molecular formula. This is due to NCERT Page-334/N-204
(a) dipolar character of ethers (b) alcohols having resonance structures
(c) inter-molecular hydrogen bonding in ethers (d) inter-molecular hydrogen bonding in alcohols
53. Which of the following has strongest hydrogen bonding?
(a) Ethyl amine (b) Ethanal (c) Ethyl alcohol (d) Diethyl ether
54. Compound I is heated with Conc. HI to give a hydroxy compound A which is further heated with Zn dust to give
compound B. Identify A and B. NCERT Page-N-213 & 218

(a) (b)

(C) (d)

55. The major organic product in the reaction, NCERT Page-348/N-218

CH3 − O − CH(CH3 )2 + HI → Product is
 (a) ICH2 OCH(CH3 )2
(b) CH3 OCI(CH3 )2
(c) CH3 I + (CH3 )2 CHOH
(d) CH3 OH + (CH3 )2 CHI
56. An aromatic ether is not cleaved by HI even at 525 K. The compound is NCERT Page-348/N-218
(a) C6 H5 OCH3
(c) C6 H5 OC3 H7
(b) C6 H5 OC6 H5
(d) Tetrahydrofuran
57. The major product [𝐵] in the following reactions is :

(a) CH2 = CH2 (b)

(C) CH3 − CH2 − (CH3 )C = CH2 (d) CH3 − CH2 − CH = CH − CH3

58. The major product of the reaction between tert-butyl chloride and sodium ethoxide is NCERT Page-346/N-216
(a) 2-methylprop-1-ene
(b) 1-butene
(c) 2-butene
(d) ethene
59. In Williamson synthesis if tertiary alkyl halide is used than NCERT Page-345 & 346/N-215 & 216
(a) ether is obtained in good yield
(b) ether is obtained in poor yield
(c) alkene is the only reaction product
(d) a mixture of alkene as a major product and ether as a minor product forms.

60.
Here⁡the⁡[X] is NCERT Page-347 & 348/N-218 & 217
(a) (b)

(C) (d)

HI NaOH
61. [𝐴] → [X] → [A]. Compound [A] is NCERT Page-N-218
(Major)
(a) (b)

(C) (d)

62. Williamson's synthesis of preparing dimethyl ether is an: CBSE Sample Paper 2021-2022]NCERT Page-345 & 346/N-215
(a) SN 1 reaction
 (b) Elimination reaction
(c) SN 2 reaction
(d) Nucleophilic addition reaction

63. NCERT Page-348/N-218

(a) (b)

(C) (d)

64. Which will not result in the formation of anisole? NCERT Page-345 & 346
OH−
(a) PhOH + CH3 Cl →
623 K
(b) Ph − Cl + CH3 ONa →
300 atm

65. Increasing order of the reactivity of the following alkyl halides in the Williamson's synthesis is NCERT Page-345 & 348
I. CH2 = CHCH2 Cl II. CH3 CH2 CH2 Br III. (CH3 )3 CCH2 Br IV. CH3 CH2 CH2 Cl
(a) II < III < IV < I
(c) IV < III < I < II
(b) III < II < IV < I
(d) IV < III < II < I
66. The acidic hydrolysis of ether (𝑋) shown below is fastest when NCERT Page-347 &348/N-217 & 218

(a) one phenyl group is replaced by a methyl group

(b) one phenyl group is replaced by a paramethoxyphenyl group
(c) two phenyl group are replaced by two paramethoxyphenyl group
(d) no structural change is made to 𝑋
 Exercise 2: NCERT Exemplar & Past Years NEET
NCERT EXEMPLAR QUESTIONS
1. Monochlorination of toluene in sunlight followed by hydrolysis with aq. NaOH yields
(a). 𝑜 - cresol
(b) 𝑚-cresol
(c) 2,4-dihydroxytoluene
(d) benzyl alcohol
2. How many alcohols with molecular formula C4 H10 O are chiral in nature? NCERT Page-326 & 327/N-196 & 197
(a) 1
(b) 2
(c) 3
(d) 4
3. What is the correct order of reactivity of alcohols in the following reaction? NCERT Page-338/N-208
ZnCl2
R − OH + HCl → R − Cl + H2 O
(a) 1∘ > 2∘ > 3∘
(b) 1∘ < 2∘ < 3∘
(c) 3∘ > 2∘ > 1∘
(d) 3∘ > 1∘ > 2∘
4. CH3 CH2 OH can be converted into CH3 CHO by NCERT Page-340/N-210
(a) catalytic hydrogenation
(b) treatment with LiAlH4
(c) treatment with pyridinium chlorochromate
(d) treatment with KMnO4
5. The process of converting alkyl halides into alcohols involves_______
(a) addition reaction
(c) dehydrohalogenation
(b) substitution reaction
(d) rearrangement reaction
6. Which of the following compounds is aromatic alcohol? NCERT Page-326/N-196 & 197

(a) A, B, C, D
(c) B, C
(b) A,D
(d) A
7. Give IUPAC name of the compound given below. NCERT Page-326/N -196

(a) 2-chloro-5-hydroxyhexane
(b) 2-hydroxy-5-chlorohexane
 (c) 5-chlorohexan-2-ol
(d) 2-chlorohexan-5-ol
8. IUPAC name of 𝑚-cresol is NCERT Page-N-197
(a) 3-methylphenol
(c) 3-methoxyphenol
(b) 3-chlorophenol
(d) benzene-1,3-diol

9. IUPAC name of the compound is_____ NCERT Page-327/N-197

(a) 1-methoxy-1methylethane
(b) 2-methoxy-2-methylethane
(c) 2-methoxypropane
(d) isopropylmethyl ether
10. Which of the following species can act as the strongest base?
(a) −OH
(b) ⁡− OR
(c) −OC6 H5

(d)
11. Which of the following compounds will react with sodium hydroxide solution in water? NCERT Page-336/N-206
(a) C6 H5 OH
(b) C6 H5 CH2 OH
(c) (CH3 )3 COH
(d) C2 H5 OH
12. Phenol is less acidic than NCERT Page-336/N-206
(a) ethanol
(b) 𝑜 - nitrophenol
(c) o-methylphenol
(d) o-methoxyphenol
13. Which of the following is most acidic? NCERT Page-N-206 & 205
(a) Benzyl alcohol
(b) Cyclohexanol
(c) Phenol
(d) 𝑚-chlorophenol
14. Mark the correct order of decreasing acid strength of the following compounds. NCERT Page-N-206

(a) I > IV > II > I > III

(b) II > IV > I > III > V
(c) IV > V > III > II > I
(d) V > IV > III > II > I
15. Mark the correct increasing order of reactivity of the following compounds with HBr/HCl. NCERT Page-N-206
 (a) I < II < III
(b) II < I < III
(c) II < III < I
(d) III < II < I
16. Arrange the following compounds in increasing order of boiling point. NCERT Page-N-203
Propan - 1 - ol, butan - 1 - ol, butan - 2 - ol, pentan - 1 - ol
(a) Propan-1-ol, butan-2-ol; butan-1-ol, pentan-1-ol
(b) Propan-1-ol, butan-1-ol, butan-2-ol, pentan-1-ol
(c) Pentan-1-ol, butan-2-ol, butan-1-ol, propan-1-ol
(d) Pentan-1-ol, butan-1-ol, butan-2-ol, propan-1-ol
17. Compounds A and C in following reaction are NCERT Page-N-201&200
(i) CH3 Mgr H2 SO4 ,Δ Hydroboration oxidation
CH3 CHO → (A) → (B) ⁡ → (C)
(ii) H2 O
(a) identical
(b) positional isomers
(c) functional isomers
(d) optical isomers

PAST YEARS NEET

18. Consider the following reaction and identify the product (P). NCERT Page-338/ N-208 ||NEET 2023, C

(a) (b) CH3 CH = CH − CH3

(C) (d)

19. Which amongst following will be most readily dehydrated under acidic conditions? NCERT-338/N-208|NEET 2023, C
(a) (b)

(C) (d)
20. Consider the following reaction : NCERT Page-347 / N-217 ||NEET 2023, C

. Identify the product A & B?

21. Given below are two statements:

Statement I: In Lucas test, primary, secondary and tertiary alcohols are distinguished on the basis of their reactivity
with conc. HCl + ZnCl2 , known as Lucas Reagent.
Statement II: Primary alcohols are most reactive and immediately produce turbidity at room temperature on reaction
with Lucas Reagent.
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 incorrect. NCERT Page-338/N-208|NEET 2022
(b) Statement I is correct but statement II is incorrect.
(c) Statement I is incorrect but statement II is correct.
(d) Both statement I and statement II are correct.
22. Given below are two statements:
Statement I: The acidic strength of monosubstituted nitrophenol is higher than phenol because of electron
withdrawing nitro group.
Statement II: 𝑜-nitrophenol, 𝑚-nitrophenol and 𝑝-nitophenol will have same acidic strength as they have one nitro
group attached to the phenolic ring.
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 incorrect. NCERT Page-341/N-206, 207|NEET 2022, C
(b) Statement I is correct but Statement II is incorrect.
(c) Statement I is incorrect but Statement II is correct.
(d) Both Statement I and Statement II are correct.
23. What is the IUPAC name of the organic compound formed in the following chemical reaction?
(i) C2 H5 MgBr, dryEther
Acetone → Pr oduct
(ii) H2 O,H+
(a) 2-methylbutan-2-ol NCERT Page-331, 324/N-201 NEET 2021, C
(b) 2-methylpropan-2-ol
(c) pentan-2-ol
(d) pentan-3-ol
24. Anisole on cleavage with HI gives NCERT Page-348/N -218 | NEET 2020, C
(a) (b)
 (C) (d)

25. The compound that is most difficult to protonate is NCERT Page-336/N-206 | NEET 2019, C

26. The compound A on treatment with Na gives B, and with PCl5 gives C. B and C react together to give diethyl ether.
A, B and C are in the order NCERT Page-345 & 346/N-345 & 346 | NEET 2018, S
(a) C2 H5 OH, C2 H6 , C2 H5 Cl
(b) C2 H5 OH, C2 H5 Cl, C2 H5 ONa
(c) C2 H5 OH, C2 H5 ONa, C2 H5 Cl
(d) C2 H5 Cl, C2 H6 , C2 H5 OH
27. Identify the major products P, Q and R in the following sequence of reactions: NCERT-332/N-202।NEET 2018, A

28. Which one is the most acidic compound ? NCERT Page-336/N-206।NEET 2017, S
(a) (b)

(C) (d)
29. The reaction NCERT Page-345/N-215 &216 | NEET 2016

Can be classified as :-
(a) Williamson ether synthesis reaction
(b) Alcohol formation reaction
(c) Dehydration reaction
(d) Williamson alcohol synthesis reaction
 ANSWER KEYS

1 (a) 8 (b) 15 (a) 22 (c) 29 (d) 36 (b) 43 (d) 50 (d) 57 (b) 64 (d)

2 (a) 9 (b) 16 (b) 23 (d) 30 (b) 37 (c) 44 (c) 51 (a) 58 (a) 65 (d)

3 (b) 10 (a) 17 (d) 24 (b) 31 (b) 38 (b) 45 (a) 52 (d) 59 (c) 66 (c)

4 (c) 11 (c) 18 (a) 25 (b) 32 (b) 39 (d) 46 (b) 53 (c) 60 (a)

5 (c) 12 (a) 19 (a) 26 (b) 33 (d) 40 (d) 47 (a) 54 (d) 61 (b)

6 (a) 13 (b) 20 (a) 27 (c) 34 (c) 41 (b) 48 (c) 55 (c) 62 (c)

7 (b) 14 (b) 21 (c) 28 (d) 35 (b) 42 (c) 49 (b) 56 (b) 63 (a)

Exercise -2 : (NCERT Exemplar & Past Years NEET)

1 (d) 4 (c) 7 (c) 10 (b) 13 (d) 16 (a) 19 (b) 22 (b) 25 (d) 28 (c)

2 (a) 5 (b) 8 (a) 11 (a) 14 (b) 17 (b) 20 (c) 23 (a) 26 (c) 29 (a)

3 (c) 6 (c) 9 (c) 12 (b) 15 (c) 18 (a) 21 (b) 24 (d) 27 (c)

 HINTS AND SOLUTIONS
EXERCISE - 1
1. (a)

in the compound, OH group is directly attach to 𝑠𝑝3 hybridised carbon.

2. (a) CH2 = CH − OH represents vinylic alcohol. In vinylic alcohols, −OH group is attached to 𝑠𝑝2 hybridised carbon
whereas in allylic alcohols, −OH group is attached to 𝑠𝑝3 hybridised carbon.
3. (b) Glycols are dihydric alcohols (having two hydroxyl groups). Ethylene glycol is the first member of this series.
4. (c) Ethers contain the functional group −O −
5. (c) In this structure-OH group is directly attached to double bonded carbon atom i.e. 𝑠𝑝2 hybridised carbon atom.
6. (a)
(i) CH3 CH2 CH(OH)CH3 (secondary)
(ii) (C2 H5 )3 COH (tertiary)
(iii)

(Phenol not an alcohol)

(iv)

7. (b)
2-Methyl-2, 4-pentanediol.
8. (b) CH3 CH2 CH(OH)CH3 is a secondary alcohol
9. (b) Cresol has phenolic- OH group
10. (a) Methyl alcohol (CH3 OH) is also known as carbinol. Hence vinyl carbinol is CH2 = CH − CH2 OH.
11. (c) The repulsion between two lone pair of electrons on oxygen atom decreases the bond angle whereas the −R
groups at 'oxygen' atom shows repulsive interaction. As a result, there is a slight increase in the bond angle.
12. (a) In alcohol, the repulsion arises from alkyl group is less than that of ether.
13. (b) The most suitable reagent for the given reaction is I2 /NaOH (Iodoform reaction).

14. (b) Reaction path follows the path of carbocation formation.

CH3 MgBr H 3 O+
(a) HCHO → CH3 CH2 OMgBr → CH3 CH2 OH
16. (b) Since the compound is formed by hydration of an alkene, to get the structure of alkene remove a molecule of
water from the alcohol.

17. (d) The aldehydes which do not have 𝛼-hydrogen atom react with NaOH when half of molecules are reduced to
alcohol and other half of molecules are oxidised to acid (Cannizzaro reaction).
2HCHO ⟶ CH3 OH − + HCOONa
Methanol ⁡ Methyl alcohol Sod. formate
18. (a) Commercially, acids are reduced to alcohols by converting them to the esters, followed by their reduction using
hydrogen in the presence of catalyst (catalytic hydrogenation).
R′ OH H2
RCOOH →+ RCOOR → RCH2 OH + R′ OH
H Catalyst
19. (a) CH3 MgBr + CH3 OH ⟶ CH3 OMgBr + CH4 ↑
20. (a) The lower alcohols are readily soluble in water and the solubility decreases with the increase in molecular weight.
The solubility of alcohols in water can be explained due to the formation of hydrogen bond between the highly
polarised - OH groups present both in alcohol and water.
21. (c) 𝑜-Nitrophenol has intramolecular H-bonding.
22. (c) Given reaction is cumene-peroxide method for the preparation of phenol. Acetone also formed in this reaction.

23. (d) [𝐴] is

24. (b) Due to partial double bond character of C − OH bond.
25. (b) Primary alcohol will favour SN 2 pathway as primary C ⊕ ion is less stable.
26. (b) Phenol is most acidic because its conjugate base is stabilised due to resonance, while the rest three compounds are
alcohols, hence, their corrosponding conjugate bases do not exhibit resonance.
27. (c) Secondary alcohols oxidise to produce ketones.

28. (d) The rates of reaction with Lucas reagent follows the order.
3∘ alcohol > 2∘ alcohol > 1∘ alcohol
 Since carbocations are formed as intermediate, more stable the carbocation, higher will be the reactivity of the parent
compound (alcohol). 2-Methylpropan-2-ol generates a 3∘ carbocation, so it will react fastest; other three generate
either 1∘ or 2∘ carbocations.
H+ Br−
(CH3 )3 − C − OH → (CH3 )3 − C ⊕ → (CH3 )3 − C − Br
2-Methyl-2-propanol
29. (d)

2, 4,6-Tribromophenol
Note : The −OH group in phenol, being activating group, facilitates substitution in the 𝑜 - and 𝑝-positions.
30. (b) Phenol is acidic enough to react with strong base NaOH but not with a weak base NaHCO3 solution. It gives violet
colour with neutral FeCl3 solution.
31. (b) Other options are acids, only Na metal is a base.
32. (b) Phenol on reaction with conc. H2 SO4 gives a mixture of 𝑜 - and 𝑝-products (i.e., −SO3 H group, occupies 𝑜−, 𝑝 -
position). At room temperature 𝑜-product is more stable, which on treatment with conc. HNO3 will yield 𝑜
nitrophenol.

At room temperature 𝑜-product is more stable

𝑜 - nitrophenol
33. (d) Tertiary alcohol is prepared by the reaction of Grignard reagent with a ketone (formaldehyde is used to prepare
primaryalcohol).

34. (c) KMnO4 (alkaline) and OsO4 /CH2 Cl2 are used for hydroxylation of double bond while O3 /Zn is used for ozonolysis.
Therefore, the right option is (c), i.e.,
BH3 in THF 3H2 O2
3CH3 CH = CH2 → (CH3 CH2 CH2 )3 B → 3CH3 CH2 CH2 OH + H3 BO3
NaOH
1-propanol
35. (b) NaBH4 and LiAlH4 attack only carbonyl group and reduce it into alcohol group.
NaBH4
C6 H5 − CH = CHCHO → C6 H5 − CH = CH. CH2 OH
Cinnamyl alcohol
Cinnamic aldehyde
36. (b)
37. (c)
38. (b) Dehydration of CH3 OH gives carbene (methylene), an unstable intermediate.
H2 SO4
CH3 OH → [: CH2 ] + H2 O
carbene
39. (d) Since the compound (C4 H10 O) reacts with sodium, it must be alcohol (option 𝑏, 𝑐, or 𝑑 ). As it is oxidised to
carbonyl compound which does not reduce Tollen's reagent, the carbonyl compound should be a ketone and thus
C4 H10 O should be a secondary alcohol, i.e. 𝑠𝑒𝑐-butyl alcohol; other two given alcohols are 1∘ .
40. (d)
P+I2 Mg HCHO H2 O
CH3 CH2 OH → CH3 CH2 I → CH3 CH2 MgI → CH3 CH2 CH2 OMgI → CH3 CH2 CH2 OH
ether
(A) (B) (C) (D)
n-propylalcohol
41. (b)

42. (c) B2 H6 selectively reduces COOH and not other groups like COCl, CHO, NO2 , etc.
43. (d) Following E1 mechanism and 1,2-methyl shift.
44. (c) Glucose and fructose obtained by hydrolysis of sucrose, are converted into alcohol by enzyme zymase.
zymase
C6 H12 O6 → 2C2 H5 OH + 2CO2
Cr O3 −ZnO
CO + H2 +
45. (a) ⏟ H2 2300 ∘C → CH3 OH
Methanol
water gas
46. (b)
Diastase
47. (a) 2(C6 H10 O5 )n + nH2 O → nC12 H22 O11 (maltose)
Starch (from germinated barley)

Maltase
C12 H22 O11 + H2 O → 2C6 H12 O6 (glucose)
(from yeast)
Zymase
C6 H12 O6 → 2C12 H22 O11
(from yeast)

48. (c) The quantity of sugar increases and yeast grows on the outer skin as grapes ripen. When grapes are crushed, sugar
and the enzyme come in contact and fermentation starts. Fermentation takes place in anaerobic contidions i.e., in
absence of air, CO2 is released during fermentation. If air gets into fermentation mixture, the oxygen of air oxidises
ethanol to ethanoic acid which in turn destroys the taste of alcoholic drinks.
49. (b) The commercial alcohol is made unfit for drinking by mixing in it some copper sulphate (to give it colour) and
pyridine (a foul smelling liquid). It is known as denaturation of alcohol.
50. (d) The two components should be (CH3 )3 CONa + (CH3 )3 CBr. However, tert-alkyl halides tend to undergo
elimination reaction rather than substitution leading to the formation of an alkene, Me2 C = CH2
51. (a) Due to H-bonding, the boiling point of ethanol is much higher than that of the isomeric diethyl ether.
52. (d) Due to inter-molecular hydrogen bonding in alcohols boiling point of alcohols is much higher than ether.
53. (c) Ethyl alcohol has strongest hydrogen bonding due to large electronegativity difference.
54. (d)

55. (c) In case of unsymmetrical ethers, the site of cleavage depends on the nature of alkyl group e.g.,

The alkyl halide is always formed from the smaller alkyl group.
56. (b) Due to greater electronegativity of 𝑠𝑝2 -hybridized carbon atoms of the benzene ring, diaryl ethers are not attacked
by nucleophiles like I − .
57. (b)

58. (a) In Williamson's synthesis the reaction of alkyl halides with sodium alkoxides give ethers. However, if the alkyl halide
is 3∘ , it undergoes elimination to give an alkene.

59. (c) If a tertiary alkyl halide is used, an alkene is the only reaction product and no ether is formed. For example, the
reaction of CH3 ONa with (CH3 )3 C − Br gives exclusively 2-methylpropene.
+
⃛ − CH3 ⟶
(CH3 )3 − C − Br + Na𝑎𝑂 (CH3 )2 − C = CH2 + NaBr + CH3 OH
2-Methylpropene
It is because alkoxides are not only nucleophiles but strong bases as well. They react with alkyl halides leading to
elimination reactions.
60. (a)
61. (b)

62. (c) Reaction since alkoxide ion reacts with primary alkyl halide in a single step to form ether. Hence, it is SN 2 reaction.
63. (a) Both the sites of epoxide group is equally hindered. So, OH − will attack on that site where electrophilicity is
maximum

64. (d) In last case CH4 is produced.

65. (d) Order of reactivity of different alkyl halides towards Williamson's synthesis is Allyl > 1∘ > 2∘ > 3∘ .
For same alkyl group order of reactivity is
𝑅 − 𝐼 > 𝑅 − Br > 𝑅 − Cl
Thus order of reactivity of given alkyl halides towards Williamson's synthesis can be given as CH2 = CHCH2 Cl (Allyl) >
CH3 CH2 CH2 Br (1 ⁡∘ bromide) > CH3 CH2 CH2 Cl(1∘ chloride ) > (CH3 )3 CCH2 Br (Stearically hindered)
66. (c) Rate of 𝑆𝑁 1 reaction is proportional to the stability of carbocation. When two phenyl groups are replaced by two
MeO − 𝐶6 𝐻4 − groups, the carbocation formed will be more stable. Hence, the reaction is fastest.

Exercise- 2
1. (d)

2. (a) Following are the three possible isomers of butanol

CH3 CH2 CH2 CH2 OH

(i) ⁡ Butan-1-ol
no chiral carbon
3. (c) HCl + An ⋅ ZnCl2 is known as lucas reagent. It is used to determine degree of an alcohol.
The reaction follow nucleophilic substitution reaction in which −OH group is replaced by −Cl. In this reaction
carbocation is formed as intermediate. Higher the stability of intermediate carbocation higher will be the reactivity of
 reactant molecule. Since 3∘ carbocation is more stable than 2∘ carbocation as well as 1∘ carbocation, so the order of
reactivity of alcohols is 3∘ > 2∘ > 1∘ .
4. (c) Less powerful oxidizing agent, Pyridinium chlorochromate (C5 H6 ClCrNO3 ) oxidises primary alcohols to aldehydes.

5. (b) The process of conversion of alkyl halides into alcohols involves substitution reaction.
OH−
R−X → R − OH
Alcohol
Alkyl halide
6. (c) Compound (A) i.e., phenol and compound (D) i.e., a derivative of phenol cannot be considered as aromatic alcohol.
On the other hand, in compounds (B) and (C), - OH group is bonded to 𝑠𝑝3 hybridised carbon which in turn is bonded
to benzene ring. Hence, are considered as aromatic.

7. (c)
8. (a) Functional group gets the priority.
9. (c)

IUPAC name of the above compund is 2-methoxypropane.

10. (b) Weakest acid has the strongest conjugate base.
Among all these acids, ROH is the weakest acid.
Therefore, the strongest base is RO- .
11. (a) Phenol being more acidic in nature reacts with sodium hydroxide solution and by the loss of one proton, it gives
phenoxide ion. This phenoxide ion is resonance stabilised.
12. (b) Presence of electron withdrawing group at ortho position increase the acidic strength. In 𝑜-nitrophenol, nitro group
is present at ortho position. On the other hand, in o-methylphenol and in o-methoxyphenol, electron releasing group
(−CH3 , −OCH3 ) are present.
Presence of these groups at ortho and para positions of phenol decreases the acidic strength of phenols. So, phenol is
less acidic than 𝑜-nitrohenol.
13. (d) Presence of electron withdrawing group increases the acidic strength. So, 𝑚-chlorophenol is most acidic among all
the given compounds.
14. (b) Electron withdrawing substituents increase the acidic strength of phenols. so, 𝑝-nitrophenol (II) and 𝑚-nitrophenol
(IV) are stronger acid than phenol (I). If −NO2 group is present at 𝑝-position, then it exerts both −I and
−Reffect, butifitis present at meta position, then it exerts only-I effect. Therefore, 𝑝-nitrophenol is stronger than 𝑚-
nitrophenol.
On the other hand, electron releasing substituents decreases the acidic strength of phenol. If −OCH3 group is present
at meta position, it will exert-I effect only.
But, if it is present at para position, it will exert +R and -I effect. Thus, 𝑚-methoxy benzyl alcohol is more acidic than 𝑝
- methoxy phenol. Hence, the correct order of decreasing acidic strength will be : II > IV > I > III > V.
15. (c) Nucleophilic substitution reactions depend upon the stability of carbocation. As, presence of electron withdrawing
group decreases the stability of carbocation in compound (II) and (III). Therefore, they will give less stable carbocation
than (I).
Since, NO2 group is a stronger EWG than −Cl.
 + +
So, NO2 − C6 H5 − CH2 will be less stable than Cl − C6 H5 − CH2
Hence, the order of reactivity of carbocatiors will be:

Therefore, the correct order is II < III < I

16. (a) With increase in molecular mass boiling point increases. Thus the b.p. of pentan-1-ol will be more than other given
compounds. Now, among isomeric alcohols 1∘ alcohols have higher boiling points than 2∘ alcohols due to higher
surface area in 1∘ alcohols.
Hence, increasing order of b.p. will be
Propan-1-ol < butan-2-ol < butan-1-ol < pentan-1-ol.
17. (b) Chemical reaction can be shown as

18. (a)

19. (b)
20. (c)

21. (b) Lucas test is used to distinguish between 1∘ , 2∘ and 3∘ alcohol on the basis of time taken for turbidity to appear by
using a solution of anhydrous ZnCl2 in conc. HCl.

22. (b) Electron withdrawing group increases the acidic character while electron donating group decreases the acidic
character. More the number of electron withdrawing group, more will be acidic strength.
 Order of acidic strength

23. (a)

24. (d)

25. (d) In lone pair of electrons present on oxygen atom is involved in delocalisation. Therefore, it is most difficult
to protonate the phenol amongst the given compounds, due to less availability of e−s .
26. (c)

27. (c)
28. (c) Electron withdrawing −NO2 group has very strong -I and -R effects, so compound (c) will be most acidic.
29. (a) This is an example of Williamson ether synthesis reaction in which sodium alkoxide reacts with alkyl halide and
gives ether.