RGANIC

CHEMISTRY
Alcohol, Phenol & Ether
Alcohols, Phenols & Ethers
Only ONE option is correct.
CH3 CH3

1. CH3 C CH CH2 CH3 C CH CH3

CH3 CH3 OH

This change can be done by

(a) acid catalysed hydration
(b) oxymercuration – demercuration
(c) hydroboration-oxidation
(d) any method mentioned above

OH OH
2. In this diol

(a) OH at C2 is more basic than that of at C5

(b) OH at C2 is more acidic than at C5
(c) both behave as a base
(d) both behave as an acid
18

3. HO OH
H3PO4

O
+ H2O
A

In this dehydration reaction, 18O will be in

(a) H2O (b) A (c) both (a) and (b) (d) none of these
4. Rate of hydration will be in order :

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

atul_rasayanam
( Alcohols, Phenols & Ethers
H3 O+ 1. B2 H6 (excess)
5. Y HC CH X.
2 2 2. H2O2 / OH

X and Y are

(a) HOH2C CH2OH , H3C CH3

HO OH
(I) (II)
(b) II, I
(c) I in both case
(d) II in both case

O CH3MgBr (excess)
O X , X is
6. H3 O
+

OH HO
OH
(a) (b) OH
H3C H3C

OH
O O
(c) (d)
CH 3

Cl Mg /ether HCHO
7. Br + A, A is
H3O

(a) Br CH2OH (b) Cl CH2OH

(c) HOH2C CH2OH (d) OHC CHO

8. CH CHCHCH CH OH MnO2 A. A is
2 2 2

OH

(a) CH CHCCH2CH2OH (b) CH2 CHCHCH2CHO

2

O OH O

(c) CH2 CHCCH2CHO (d) CH CHCCH2COH

2

O O
( Alcohols, Phenols & Ethers

MnO2
9. OH A, A is

OH

(a) OH (b) O (c) O (d) O

O OH O OH

O A O
10. O O A is
COOH CH2OH

(a) B2H6/H2O (b) LiAlH4 (c) CH3OH/Na (d) P/HI

+
H3O
11. Ester A(C4H8O2) + CH3MgBr C4H10O
(2 parts) (alcohol B)
Alcohol B reacts fastest with Lucas reagent. Hence, A and B are
O O

(a) CH3COC2H5 , (CH3)3COH (b) HCOC3H7 , (CH3)2CHOH

O O

(c) CH3COC2H5 , (CH3)2CHOH (d) HCOC3H7 , (CH3)3COH

CH3
cold CrO3
12. A B , A and B are
alkaline KMno4 AcOH

H
(a)
,
OH O

(b)
,
OH O
( Alcohols, Phenols & Ethers

CH3
CH3
OH
(c)
, OH
OH

(d) No formation of A and B

NaBH4 H2/Pt
13. B CH CHCHO A,

A and B are

(a) CH2CH2CHO , CH CHCH2OH

(b) CH2CH2CH2OH , CH CHCH2OH

(c) CH CHCH2OH

(d) CH2CH2CH2OH

14. Oxo process

(a) is simply carbonylation or hydroformylation reaction
(b) uses cobalt carbonyl hydride [CoH(CO)4] as catalyst
(c) both statements are correct
(d) both statements are incorrect
+
H3O HBr Mg/ether
15. CH3MgBr + A B C

O HCHO
D , D is
H3O+

OH
(a) (b) (c) (d)

H3C CH2OH CH2OH CH3

CH3 CH3 CH2OH
( Alcohols, Phenols & Ethers
H3O
16. R MgBr + A CH CH CH ORH a, n d A are
3 2 2

(a) CH3CH2 and HCHO (b) CH3 and CH2 CH2

(c) both (a) and (b) are correct (d) none of the ab oOv e is correct

17. HBO, oxymercuration-demercuration and acid catalysed hydration will give same product in

(a) (b) (c) (d)

18. Rank the transition states that occur during the following reaction steps in order of increasing
stability (least most stable).
+
1. H3C OH2 CH+3 + H2O
+
2. (CH3)3 C OH2 (CH3)3 C+ + H2O

+
3. (CH 3) 2 CH OH 2 (CH3)2 CH + H2 O

(a) 1 < 2 < 3 (b) 2 < 3 < 1 (c) 1 < 3 < 2 (d) 2 < 1 < 3

19. What is the major product of the following reaction ?

O

NaBH4
?
CH3OH
CO2H

OH O OH OH

(a) (b) (c) (d)

CH2OH CH2OH CO2H CO2CH3

20. What is the major organic product of the following sequence of reaction ?

PBr3 Mg H2C CH2

(CH3) 2CHCH2OH ?

OH OH

(a) (CH3)2CHCHCH2CH3 (b) (CH3)2 CHCH2 CHCH3

(c) (CH3)2 CHCH2 CH2 OH (d) (CH3)2 CHCH2CH2CH2OH

( Alcohols, Phenols & Ethers
21. Match the following
Column I Column II
(Alcohol/intermediate) (Grignard synthesis)
+
H O
CH CH + CH MgBr 3
A CH3CH2CH2OH P 2 2 3

CH3CHOH +
H 3O
B Q CH 3CH2 MgBr + HCHO
CH3

CH3 O
H 3O+
C CH3COH R CH 3COCHCH 3+ 2CH3MgBr

CH3 CH3

O
+
D CH3CHO (intermediate) S H3O
HCCH3 CH3 + 2CH3MgBr

Single Integer Answer Type

22. The number of structural isomers of C4H10O are …………

23. Alcoholic group at position ............... Reacts fastest with Lucas’ reagent.
O OH
HO OH
2 4
1 3 5
OH

24. Alcoholic group at position is oxidised to carbonyl group by copper metal.

25. Vitamin C also called ascorbic acid has number of COOH group ………… .

26. 30 g of CH3MgBr reacts with excess of CH3CH2CH2OH forming x g of a gas. x is ……….. .

Step-Through Questions

27. Write the major addition product of

H2SO4
+ CH 3OH ...........
(a)
H SO
(b) + CH OH ...........
CH3 2 4
3
 Alcohols, Phenols & Ethers

(c) H2SO4
CH 3 + CH 3OH ...........

Hg(OAc)2 NaBH4
28. A, A is
CH3OH

(a) OH (b) (c) OCH3 OCH 3

OH
mCPBA
29. CH2Cl2 A, A is

OH
(a) (b) (c) (d) OH
OH
OH

30. Decreasing order of reactivity of following alkyl halides in the Williamson’s ether synthesis is
(CH3)3CCH2Br (A), ClCH2CH CH2 (B), ClCH2CH2CH3 (C), BrCH2CH2CH3 (D)
(a) B > D > C > A (b) A > B > C > D (c) D > C > B > A (d) C > D > B > A
31. Consider the reaction of HI with the following

I: II :
O

Which forms di-iodide on reaction with HI (excess) ?

(a) I, II (b) II (c) I (d) none of these
O

O A
32. OH OH
OH

Reagent A used in this change is

(a) B2H6 (b) LiAlH4 (c) Sn/HCl (d) CH3OH./Na
33. Which is not cleaved by HIO4 ?
I : glycerol II : glycol III : 1, 3-propanediol IV : methoxy-2-propanol
(a) I, II, III, IV (b) I, II (c) II, III (d) III, IV
 Alcohols, Phenols & Ethers
OH

34. OC2H5
+ C2H5 I anhy. C H OH
2 5

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

35. Total number of isomeric alcohols with formula C4H10O is :
(a) 2 (b) 1 (c) 3 (d) 4
36. Number of isomers represented by molecular formula C4H10O is :
(a) 3 (b) 4 (c) 7 (d) 10
37. Lucas reagent is :
(a) anhydrous ZnCl2 and conc. HCl (b) anhydrous ZnCl2 and conc. HNO3
(c) hydrous ZnCl2 and conc. HNO3 (d) hydrous ZnCl2 and conc. HCl
38. Which one of the following alcohols reacts most readily with Lucas reagent ?
(a) CH3CH2CH2OH (b) CH CHOH
3

CH3 CH3

(c) CH3 C OH (d) CH3 CH2OH

CH3

39. Primary, secondary and tertiary alcohols are distinguished by :

(a) oxidation method (b) Lucas test
(c) Victor Meyer’s method (d) all of the above
40. Reaction, CO + H + H 673 K, 300 atm.
?
2 2
water gas Cr2O 3 ZnO

may be used for manufacture of :

(a) HCHO (b) CH3COOH (c) HCOOH (d) CH3OH
41. Which reagent can bring about,
R COOH R CH2OH
(a) Sn + HCl (b) LiAlH4 (c) Na and C2 H5OH (d) H2 and Pt
42. Glucose and fructose are converted into C2H5OH in presence of :
(a) invertase (b) diastase (c) zymase (d) lipids
43. The reason for high boiling points of alcohols as compared to isomeric ethers is :
(a) solubility of alcohols in water (b) higher reactivity
(c) association in molecules due to hydrogen bonding (d) none of the above
44. Which one is not characteristic of alcohols ?
(a) They are lighter than water
(b) Their boiling points rise uniformly with rising molecular weight
(c) Lower members are insoluble in water but solubility increases regularly
(d) Lower members have a pleasant odour and burning taste
 Alcohols, Phenols & Ethers
45. Formaldehyde forms an addition product with CH3MgI which on hydrolysis gives :
(a) ethyl iodide (b) ethyl alcohol (c) methyl alcohol (d) methyl iodide
46. When CH3MgI is made to react with acetone and the addition product is hydrolysed, we get :
(a) primary alcohol (b) secondary alcohol (c) tertiary alcohol (d) an aldehyde
47. Identify (Z) in the following reaction series :
PBr3 Alc. KOH H2SO4, room temp.
Ethanol (X) (Y) (Z)
H2O, heat

(a) H C CH2 (b) CH3CH2OH (c) CH3CH2OSO3H (d) C2H5OC2H5

2
48. Lucas test is used for the determination of :
(a) aldehydes (b) phenols (c) carboxylic acids (d) alcohols
49. For a given alcohol, the order of reactivity with halogen acids is :
(a) HI > HBr > HCl (b) HI > HCl > HBr
(c) HCl > HBr > HI (d) HBr > HI > HCl
50. Which of the following compounds is commonly used as antifreeze in automobile radiators ?
(a) CH3OH (b) C2H5OH (c) Glycerol (d) All of these
51. Glycerol is more viscous than ethanol due to :
(a) many hydrogen bonds per molecule (b) Fajan’s rule
(c) high boiling point (d) high molecular weight
52. Which of the following compounds will form a hydrocarbon on reaction with a Grignard
reagent?
(a) CH3CH2OH (b) CH3CHO (c) CH3COCH3 (d) HCHO
53. Which of the following reagents can convert acetic acid into ethanol ?
(a) Sn + HCl (b) H2 + Pt (c) LiAlH4 + ether (d) Na + alcohol
54. Identify (Z) in the series,
Conc. H2SO4 Br2 Excess of
C3H7OH (X) (Y) (Z)
o
170 C Alc. KOH

(a) CH CH CH2 (b) CH3 CH CH2

3

NH2 NH2 OH OH

(c) CH3 C CH2 (d) CH3 C CH2

OH
55. When 3,3-dimethyl butan-2-ol is heated with conc. H2SO4 the major product obtained is:
(a) 2,3-dimethyl but-1-ene (b) 3,3-dimethyl but-1-ene
(c) 2,3-dimethyl but-2-ene (d) cis and trans isomers of 2,3-dimethyl but-2-ene
56. The dimer of methanol will have the structure:
H
O O CH3
(a) H O C H O CH3 (b) CH3 .
H H
H H
 Alcohols, Phenols & Ethers

(c) H O CH3 CH3 O H (d) CH3 O H O CH3

H
57. 2-Phenylethanol may be prepared by the reaction of phenyl magnesium bromide with:
(a) HCHO (b) CH3CHO (c) CH3COCH3 (d) CH2 CH2
58. Vinyl carbinol is:
OH O

(a) HO (b) CH3 C CH2

CH2 CH CH2
(c) CH3 CH CH OH (d) CH3 C(CH2OH) CH2
59. An organic compound (A) reacts with methyl magnesium 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, tertiary butyl alcohol (b) acetaldehyde, ethyl alcohol
(c) acetaldehyde, isopropyl alcohol (d) acetone, isopropyl alcohol
60. How many optically active stereoisomers are possible for butan-2,3-diol?
(a) 1 (b) 2 (c) 3 (d) 4
61. The order of reactivity of the following alcohols towards conc. HCl is :
CH3
CH3 CH3
CH3

F OH PH
F OH
OH OH

(I) (II) (III) (IV)

(a) I > II > III > IV (b) I > III > II > IV (c) IV > III > II > I (d) IV > III > I > II
62. (CH3)3 CMgBr on reaction with D2O produces :
(a) (CH3)3CD (b) (CH3)3COD (c) (CD3)3 CD (d) (CD3)3OD
63. In the reaction given below, X is :
H2SO4
Neo-pentylalcohol X
(a) 2-methylpentane (b) Neo-pentane (c) 2-methylpent-2-ene (d) 2-methylbut-2-ene
64. Which one/ones of the following reactions will yield 2-propanol ?
H+ (i) CH3MgI
(i) CH CH CH + H O (ii) CH CHO
3 2 2 3 (ii) H2O

(iii) HCHO (i) C2H5MgI (iv) CH CH CH Neutral KMnO4

(ii) H2O 3 2

Choose the right answer :

(a) (i) and (ii) (b) (ii) and (iii) (c) (iii) and (i) (d) (ii) and (iv)
 Alcohols, Phenols & Ethers
65. Which of the following enzymes convert glucose into ethyl alcohol ?
(a) Diastase (b) Invertase (c) Maltase (d) Zymase
66. Ethyl acetate reacts with CH3MgBr to form :
(a) secondary alcohol (b) tertiary alcohol
(c) primary alcohol and an acid (d) an acid

67. The correct order of boiling points for primary (1o), secondary (2o) and tertiary alcohol (3o) is:
(a) 1o > 2o > 3o (b) 3o > 2o > 1o (c) 2o > 1o > 3o (d) 2o > 3o > 1o
68. Which one of the following will most readily be dehydrated in acidic condition ?
O OH OH O O
(a) (b) (c) (d)

69. What is the formed when glycerol reacts with HIO4 ? OH OH

(a) Two molecules of formic acid and one molecule of formaldehyde
(b) Two molecules of formaldehyde and one molecule of formic acid
(c) Three molecules of formic acid
(d) Three molecules of formaldehyde
70. During dehydration of alcohols to alkenes by heating with conc. H2SO4, the initiation step is :
(a) elimination of water (b) formation of an ester
(c) formation of carbocation (d) protonation of alcohol molecule
71. Which of the following functional groups, cannot be reduced to alcohol using NaBH4 in ethanolic
solution ?
(a) R O R (b) RCOCl (c) R COOH (d) R CHO
72. Acetyl bromide when reacts with excess of CH3MgI followed by treatment with saturated
solution of NH4Cl it gives :
(a) acetone (b) acetamide (c) 2-methyl-2-propanol (d) acetyl iodide
73. Among the following compounds which can be dehydrated very easily ?
OH

(a) CH CH CH CH CH OH (b) CH3CH2CH2CHCH3

3 2 2 2 2

CH3

(c) CH3CH2 C CH2CH3 (d) CH3CH2CHCH2CH2OH

OH CH3

74. CH3 +
H Br2
[F] C4H8Br2
H2O CCl4
5 such products
H3C OH are possible

How many structures of [F] are possible ?

(a) 2 (b) 5 (c) 6 (d) 3
 Alcohols, Phenols & Ethers
75. The best reagent to convert pent-3-en-2-ol into pent-3-en-2-one is :
(a) acidic permanganate (b) acidic dichromate
(c) chromic anhydride in glacial acetic acid (d) pyridinium chlorochromate

76. 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
77. Which will give chiral molecule ?
LiAlH4
CH3MgBr
(a) CH 3COCl (b) C2H5 CHO +
/H O
H 2

H
Cu CH3
(c) (CH ) COC H (d) C C Cl2
3 2 2 5
H3C CH3
78. A compound ‘X’ undergoes reduction with LiAlH4 to yield ‘Y’. When vapours of ‘Y’ are passed
over freshly reduced copper at 300oC, ‘X’ is formed. What is ‘Y’ ?
(a) CH3COCH3 (b) CH3CHO (c) CH3CH2OH (d) CH3 O CH3
79. In the Victor Meyer’s test, the colours given by 1o, 2o and 3o alcohols are respectively :
(a) red, colourless, blue (b) red, blue, colourless
(c) colourless, red, blue (d) red, blue, violet (e) blue, red, violet
80. The major product formed in the following reaction is :
Aq. KOH
CH3CH(Cl)CH2CH 2OH

(a) CH3CH CHCH2OH (b) CH2 CHCH2CH2OH

(c) CH3 CH CH2 (d) CH3 CH CH2CH2OH

O CH2 OH

81. Phenyl magnesium bromide reacts with methanol to give :

(a) a mixture of anisole and Mg(OH)Br (b) a mixture of benzene and Mg(OMe)Br
(c) a mixture of toluene and Mg(OH)Br (d) a mixture of phenol and Mg(Me)Br
82. In the following sequence of reactions,
P + I2 Mg H2O
CH CH OH (A) (B) HCHO (C) (D)
3 2 ether

the compound D is :
(a) propanal (b) butanal (c) n-butyl alcohol (d) n-propyl alcohol

H3C
83. P + Br2 Na
CH OH (X)
H3C

(X) is :
 Alcohols, Phenols & Ethers

CH3 CH3

(a) CH3 CH CH2CH3 (b) CH3 C CH3

CH3

CH3
H3C CH3
(c) CH CH (d) CH3 CH CH2CH2CH3
H3C CH3

84. The strongest acid is :

(a) HC CH (b) C6H6 (c) C2H6 (d) CH3OH
85. The function of ZnCl2 in Lucas test for alcohols is :
(a) to act as an acid catalyst and react with HCl to form H2ZnCl4
(b) to act as a base catalyst and react with NaOH to form Na2Zn(OH)4
(c) to act as an amphoteric catalyst
(d) to act as a neutral catalyst
86. Grignard reagents give alkane, on reaction with :
(a) phenol (b) ether (c) alcohol (d) water
87. Alcohols act as :
(a) oxidising agent (b) reducing agent (c) Lewis base (d) Bronsted acid
88. Ethanol can be converted to propane nitrile (CH3CH2CN) by the following reaction(s):

(a) CH3CH2CH2OH + KCN

(b) CH3CH2OH + HCN

TsCl KCN
(c) CH CH OH CH CH OTs
3 2 Pyridine 3 2

PCl5 NaCN
(d) CH CH OH CH CH Cl CH CH CN
3 2 POCl3, HCl 3 2 NaCl 3 2

89. Alcohol can be prepared by which of the following methods ?

(a) By hydration of alkene
(b) By reduction of carbonyl compounds
(c) By reaction of primary aliphatic amines with nitrous acid
(d) By hydrolysis of esters
90. 1o, 2o and 3o alcohols can be distinguished by :
(a) Cu/573 K (b) Victor Meyer’s test (c) conc.HCl/ZnCl2 (d) Br2 water
91. Alcoholic group can be replaced by – Cl group by the following reagents :
(a) Cl2 (b) SOCl2 (c) PCl5 (d) HCl and ZnCl2
 Alcohols, Phenols & Ethers
This set contains questions with single correct answer :
92. Ethers are isomeric with monohydric alcohols. Both have the general formula :
(a) CnH2n+2O (b) CnH2nO (c) CnH2n+4O (d) CnH2n-2O
93. The IUPAC name of CH3OC2H5 is :
(a) ethoxy methane (b) methoxy ethane (c) ethyl methyl ether (d) methyl ethyl ether
94. The reaction,
C2 H5ONa + C2H5I C2H5OC2 H5 + NaI
is called
(a) Wurtz reaction (b) Kolbe’s reaction
(c) Williamson’s synthesis (d) Grignard synthesis
95. The product (D) in the following sequence of reactions is :
HBr NaOH(aq.) Na CH3I
C2H5 (A) (B) (C) (D)
(a) butane (b) ethane (c) propane (d) ethyl methyl ether
96. Ethers are obtained by reacting alkyl halides with :
(a) dry Ag2O (b) moist Ag2O (c) dry ZnO (d) moist ZnO
97. According to Lewis concept of acids and bases, ethers are :
(a) neutral (b) acidic (c) basic (d) amphoteric
98. Oxygen atom of ether is :
(a) very active (b) replaceable (c) active (d) comparatively inert
99. The hybrid state of central oxygen atom in diethyl ether is :
(a) sp2 (b) sp3 (c) sp (d) sp3d

100. Ethoxy ethane does not react with :

(a) HI (b) conc. H2SO4 (c) PCl5 (d) Na

101. In [18]-crown-6, the number of oxygen atoms is:

(a) 18 (b) 6 (c) 12 (d) 24

102. CH2 CH2 + LiAlH4 (A), (A) is :

O

(a) CH3CHO (b) CH3CH2OH (c) H2C CH2 (d) CH2OH CH2OH
H2O
103. CH3MgI + ............. + 1-Propanol,
H

the missing reagent is:

(a) HCHO (b) C2H5OH (c) C2H5Cl (d) ethylene oxide
104. In the following reaction,
CH O CH + 4H Red P 2X + H O, X is :
2 5 2 5 2
HI
(a) ethane (b) ethylene (c) butane (d) propane
 Alcohols, Phenols & Ethers
105. Which of the following will not give anisole ?
(a) Phenol is reacted with dimethyl sulphate in presence of a base
(b) Sodium phenoxide is treated with methyl iodide
(c) Diazomethane is reacted with phenol
(d) Methyl magnesium iodide is treated with phenol

106. Anisole on treatment with Br2/CS2 gives :

(a) bromobenzene (b) methyl-2-bromophenyl ether
(c) o- and p-bromoanisole (d) phenol

107. Which of the following is not cleaved by HI even at 525K ?

(a) C6H5 O CH3 (b) C6H5 O C6H5

(c) C H OC H (d)
6 5 3 7
O

108. In Williamson’s synthesis, ethoxy ethane is prepared by :

(a) passing ethanol over heated alumina
(b) heating ethanol with dry Ag2O
(c) heating sodium ethoxide with ethyl bromide
(d) treating ethyl alcohol with excess of H2SO4 at 430-440 K
109. In which of the following reactions, ethyl chloride is not formed ?

(a) C2 H5OC2H5 + PCl5 (b) C2 H5OC2H5 + CH3COCl

hv
(c) C H OC H + Cl (d) C2 H5OH + PCl3
2 5 2 5 2

CH3 C OC2H5 Na C2H5OH

110. CH MgX (A) (B) (C),
+
3
H , H O
2

(C) is :
O

(a) CH3 C CH3 (b) (CH3)3C O C2H5

(c) C2H5OC2H5 (d) CH C OC2H5

3

111. In the reaction,

CH3 Heated ..........
CH CH2 O CH2 CH3 + HI

CH3
 Alcohols, Phenols & Ethers
Which of the following compounds will be formed ?
(a) CH3 CH CH2OH + CH3CH3 (b) CH3 CH CH3 + CH3CH2OH

CH3 CH3

(c) CH3 CH CH2OH + CH3CH2I (d) CH3 CH CH2I + CH3CH2OH

CH3 CH3

112. From Williamson’s synthesis, the preparation of which of the following is possible ?
(a) Only symmetrical ethers (b) Only asymmetrical ethers
(c) Both (a) and (b) (d) None of the above
113. In which of the following reactions, the product obtained is tert. Butyl methyl ether?

CH3
(a) CH OH + HOCH CH Conc. H2SO4 (b) CH3 C Br + CH3OH HONa+
3 2 3

CH3

CH3 CH3
+ +
(c) CH3Br + Na O C CH3 (d) CH3 ONa + CH3 C Br

CH3 CH3

This set contains the questions with two or more correct answers :

114. The ether O CH2 when treated with HI produces :

(a) CH2I (b) CH2OH

(c) I (d) OH

115. Which of the following reactions will give good yield of ether ?

OH OC2H5
(i) Na
(a) (ii) C H Br
2 5

(i) Na C6H5 O C(CH3)3

(b) (CH3)3C OH (ii) C H Br
6 5

(i) Na
(c) (CH3)3C OH (ii) CH CH CH Br (CH3)3C O CH2CH2CH3
3 2 2

(d) CH CH CH OH (i) Na (CH ) C O CH CH CH

3 3 2 2 3
3 2 2 (ii) (CH3)3CBr
 Alcohols, Phenols & Ethers
116. Diethyl ether on treatment with HI in small amount, gives:
(a) C2H5OH (b) C2H5I (c) C4H10 (d) C3H7I

More than one Correct type Questions:

Q.1. Choose incorrect statements regarding the following reaction

(a) Syn addition of –H (from BH3 ) and –OH (from solution) occur

(b) Syn addition of –H (from

BH3 ) and –OH (from H O ) occur
2 2

(c) The product is optically active

(d) Addition follows anti Markownikoff orientation

Q.2.
OH

Which of the following are possible products in significant amounts ?

(a)
= Br

Br CH2
(c)

Q.3. H3C H H3C

H OH H

Which of the following represent conditions to perform given conversion ?

(a) POCl3 , pyridine

(b) Na-metal, CS2 , heat

H3C SO 2 Cl, pyridine ; CH 3 CH 2 O/CH 3 CH 2 OH

(c)

(d) CF SO Cl, pyridine ; Me COK

3 2 3
 Alcohols, Phenols & Ethers
Q.4. Which of the following alcohols do not give white turbidity on treatment with HCl/ ZnCl2 ?

(a) CH3CH2OH (b)

CH2OH

CH3

(c) N  C − CH − OH (d) CH3 H OH

|
CH3
CH3
Q.5. Which of the following will give iodorom ?

OH
|
(a) CH3CH2OH (b) CH3 − CH− Ph

OH

(c) (d)

OH OH

Q.6. Which of the following ethers will get hydrolysed by HI ?

(a) O (b) O

(c) (d)
O O O CH3

Q.7. Which of the following reactions are correctly matched ?

CH3
|

(a) CH3 −C −O − CH 3 ⎯H⎯I→SN 1 (b) CH3 − CH −O − CH 3 ⎯H⎯⎯H2⎯→SN1
/ O

| |
CH3 CH3
(c) CH − CH −O − CH ⎯H⎯I→S 2 (d) CH − O − CH CH ⎯H⎯I→S 1
3 3 N 3 2 3 N
|
CH3
Q.8. Which of the following compounds will give positive Victor Meyer test ?
 Alcohols, Phenols & Ethers
CH3
|
(a) CH3CH2OH (b) CH3 −C− OH
|
CH3

CH3
|
(c) CH3CH2 − I (d) CH3 −CH − NO2

Q.9. Which of the following alcohols undergo rearrangement during dehydration reaction ?

CH3 OH
|
(a) CH3 − C − CH− CH3 (b)
| |
CH3 OH

OH
CH3
|
(c) (d) Ph − CH −CH− CH3
|
OH

Q.10. C2 H5OC2 H5 and can be distinguished by

(a) aq, FeCl3 (b) Na metal (c) Tollen’s reagent (d) K2Cr2O7

O CH2
Q.11. The ether when treated with HI produces

C H 2O H
CH2I
(a) (b)

(c) I (d) OH

Q.12. Which of the following reaction will give ether as main product ?

OH
Na
Me C − OH ⎯N⎯a→
(a) (b) 3
C2H5Br C6H5 Br
 Alcohols, Phenols & Ethers
(c) Me C − OH ⎯ ⎯→ N a
(d) CH CH CH Br ⎯⎯→
N a

3 3 2 2
CH3 CH2CH2Br Me3C−Br

Q.13. C2 H5Br can be converted into C2 H5 − O − C2H5 by:

(a) reacting by C2 H5ONa (b) heating with moist Ag2O

(c) heating with dry Ag2O (d) treating with C2 H5MgBr

Q.14. 1°, 2° and 3° alcohols can be distinguished by

(a) Cu/573 K (b) Victor Meyer test

(c) ZnCl2/HCl (d) Br2 + H2O

Q.15. Alcohols cn be replaced by –Cl group by the following reagents

(a) Cl2 (b) SOCl2 (c) PCl5 (d) HCl + ZnCl2

Q.16. Glycerol can be converted to acrolein by dehydration in presence of

(a) Conc. H2SO4 (b) KHSO4 (c) CaCl2 (d) Anhyd. ZnCl2

Q.17. CH3CH2 − OH can be converted to CH3CH2CN by the following reactions

(a) CH 3CH 2OH + KCN ⎯⎯→ (b) CH 3CH 2OH + HCN ⎯⎯→

(c) CH 3CH 2OH ⎯T⎯sC⎯

l →⎯⎯KCN⎯→ (d) CH 3CH 2OH ⎯⎯SOC⎯
l 2→ ⎯⎯KCN⎯→

Q.18. Which of the following will oxidize to salt of acid by Br2 + KOH ?
OH
(a) CH3 − CH2 − OH (b)
CH CH3

OH
(c) (d) CH2OH
OH

Q.19. H H TsCl
A NaBr B
Pyridine
H3C OH

Br
(a) H H (b) B is
A is H3C H
H3C OH

H H
A is B is
(c) Ts (d)
H2C Br
 Alcohols, Phenols & Ethers

Conc.H2SO4 O3 OH
Q.20. A B C
OH  
O

O
A is B is
(a) (b)

C is O C is O
(c) (d)

Answer Keys (Objective)

Only one option is Correct
1 B 2 A 3 A 4 A 5 A 6 A 7 B 8 A
9 B 10 A 11 A 12 A 13 B 14 C 15 A 16 C
17 C 18 C 19 B 20 D 21 22 7 23 3 24 6
25 4 26 4 27 28 D 29 B 30 A 31 C 32 B
33 D 34 B 35 D 36 C 37 A 38 C 39 D 40 D
41 B 42 C 43 C 44 C 45 B 46 C 47 B 48 D
49 A 50 C 51 A 52 A 53 C 54 C 55 C 56 D
57 D 58 A 59 C 60 B 61 C 62 A 63 D 64 A
65 D 66 B 67 A 68 A 69 B 70 D 71 A 72 C
73 C 74 D 75 D 76 B 77 B 78 C 79 B 80 D
81 B 82 D 83 C 84 D 85 A 86 ACD 87 CD 88 CD
89 ABCD 90 ABC 91 BCD 92 A 93 B 94 C 95 D 96 A
97 C 98 D 99 B 100 D 101 B 102 B 103 D 104 A
105 D 106 C 107 B 108 C 109 C 110 B 111 C 112 C
113 C 114 A 115 AC 116 AB

Answer key (More than one Correct)

1 A, c 2 B,c,d 3 B,c,d 4 A,c 5 A,b,d
6 C,d 7 A,b,c 8 A,c,d 9 A,b,d 10 B,d
11 A,d 12 A,c 13 A,b 14 A,b,c 15 B,c,d
16 A,b 17 C,d 18 A, b 19 A, b 20 A, b,d
ALCOHOL, PHENOL & ETHER (JEE-MAIN)
1. Picric acid is - [AIEEE-2002]

OH
COOH COOH COOH
2

(A) (B) (C) (D)

NO2 OH NO2 NH2

2. Maximum dehydration takes place that of - [AIEEE-2002]

(A) (B) (C) (D)

3. The reaction of chloroform with alcoholic KOH and p-toluidine form- [AIEEE-2003]

(A) H3C CN (B) H3C N2Cl

(C) H3C NHCHCl2 (D) H3C NC

4. An ether is more volatile than an alcohol having the same molecular formula. This is due to -
[AIEEE-2003]
(A) Inter molecular hydrogen bonding in ethers (B) Inter molecular hydrogen bonding in alcohols
(C) Dipolar character of ethers (D) Alcohols having resonance structures

5. When CH2 = CH–COOH is reduced with LiAlH4, the compound obtained will be - [AIEEE-2003]
(A) CH3–CH2–CH2OH (B) CH3–CH2–CHO (C) CH3–CH2–COOH (D) CH2=CH–CH2OH

6. The general formula CnH2nO2 represents [AIEEE-2003]

(A) Diols (B) Dialdehydes (C) Diketones (D) Carboxylic acids

7. Among the following compounds which can be dehydrated very easily is - [AIEEE-2004]

OH

(A) CH3CH2CH2CH2CH2 OH (B) CH3 CH2CH2CHCH3

CH3
(C) CH3CH2C CH2CH3 (D) CH CH CH CH CH OH
3 2 2 2

OH CH3

22
8. p-cresol reacts with chloroform in alkaline medium to give the compound A which adds hydrogen cyanide to
form, the compound B. The later on acidic hydrolysis gives chiral carboxylic acid. The structure of the
carboxylic acid is - [AIEEE-2005]

CH3 CH3
CH(OH)COOH
(A) (B)
CH(OH)COOH
OH OH

CH3
CH3
CH2 COOH
(C) (D)
CH2COOH
OH
OH

9. The best reagent to convert pent–3–en–2–ol into pent –3–en –2–one is - [AIEEE-2005]
(A) Acidic dichromate (B) Acidic permanganate
(C) Pyridinium chloro-chromate (D) Chromic anhydride in glacial acetic acid

10. Among the following the one that gives positive iodoform test upon reaction with I2 and NaOH is-
[AIEEE-2006]
(A) CH3CH2CH(OH)CH2CH3 (B) C6H5CH2CH2OH
CH3

(C) H3C (D) PhCHOHCH3

OH

11. HBr reacts with CH2 = CH – OCH3 under anhydrous conditions at room temperature to give -
(A) BrCH2CHO and CH3OH (B) BrCH2–CH2–OCH3 [AIEEE-2006]
(C) H3C–CHBr–OCH3 (D) CH3CHO and CH3Br

12. The structure of the compound that gives tribromo derivative on treatment with bromine water is -
[AIEEE-2006]

CH2OH CH CH3 CH3

OH
(A) (B) (C) (D)
OH
OH

13. In the following sequence of reactions

CH CH OH P+ I A Mg B HCHO
2

C
H2O D, then compound 'D' is - [AIEEE-2007]
3 2 Ether
(A) butanal (B) n–butyl alcohol (C) n–propyl alcohol (D) propanal

14. Phenol, when it first reacts with concentrated sulphuric acid and then with concentrated nitric acid, gives
[AIEEE-2008]
(A) 2, 4, 6– trinitrobenzene (B) o–nitrophenol
(C) p–nitrophenol (D) nitrobenzene

23
15. The major product obtained on interaction of phenol with sodium hydroxide and carbon dioxide is :-
[AIEEE-2009]
(A) Salicylic acid (B) Phthalic acid (C) Benzoic acid (D) Salicyladehyde

16. From amongst the following alcohols the one that would react fastest with conc. HCl and anhydrous ZnCl2,
is :- [AIEEE-2010]

(A) 1–Butanol (B) 2–Butanol (C) 2–Methylpropan–2–ol (D) 2–Methylpropanol

17. Sodium ethoxide has reacted with ethanoyl chloride. The compound that is produced in the above reaction
is :- [AIEEE-2011]

(A) Ethyl chloride (B) Ethyl ethanoate (C) Diethyl ether (D) 2–Butanone

18. Phenol is heated with a solution of mixture of KBr and KBrO3. The major product obtained in the above
reaction is :- [AIEEE-2011]

(A) 4-Bromophenol (B) 2,4,6-Tribromophenol

(C) 2-Bromophenol (D) 3-Bromophenol

19. Compound (A), C8H9Br, gives a white precipitate when warmed with alcoholic AgNO3. Oxidation of (A)
gives an acid (B), C8H6O4. (B) easily forms anhydride on heating. Identify the compound (A) :
[JEE-MAIN 2013]

CH2Br
CH2Br C2H5 CH2Br
(A) (B) (C) (D)
Br CH3
CH3 CH3

20. An unknown alcohol is treated with the "Lucas reagent' to determine whether the alcohol is primary, secondary
or tertiary. Which alcohol reacts fastest and by what mechanism :- [JEE-MAIN 2013]

(A) secondary alcohol by SN1 (B) tertiary alcohol by SN1

(C) secondary alcohol by SN2 (D) tertiary alcohol by SN2

21. In the reaction CH 3COOH ⎯⎯LiA⎯

l H4→ A ⎯⎯P⎯Cl5→ B ⎯⎯AlC .⎯K
O⎯H→ C the product C is [JEE MAIN 2014]

(A) Ethylene (B) Acetyl chloride

(C) Acetaldehyde (D) Acetylene

24
22. Sodium phenoxide when heated with CO2 under pressure at 1250 C yields a product which on acetylation
produces C. [JEE MAIN 2014]

ONa

125c H+
+CO2 5 Atm B Ac2O C

OCOCH3
OH
COOCH3

(A) (B)
COOH
OH
COCH3
OCOCH3
COOH
(C) (C)

COCH3

23. The most suitable reagent for the conversion of R − CH 2 − OH → R − CHO is [JEE MAIN 2014]

(A) CrO 3 (B) PCC (Pyridinium chlorochromate )

(C) KMnO4 (D) K2Cr2O7

24. 2-chloro-2-methylpentane on reaction with sodium methoxide in methanol yields: [JEE MAIN 2016]

CH3
C2 H5CH2 C = CH 2
(3). C2 H5CH = C| − CH3
|

(1). C2 H5CH2 C| − OCH3 (2). |

CH3 CH3 CH3

(A) 1 And 3 (B) 3 only (C) (1) and (2) (D) all of these

25. Phenol reacts with methyl chloroformate in the presence of NaOH to form product A. A reacts with Br2 to
form product B. A and B are respectively. [JEE MAIN 2018]

OH Br OH

(A) and
OCH3 OCH3

O O

25
 O O O O

(B) O and O

Br

O O O O

(C) O and O

Br

OH
OH
and
(D) OCH3
OCH3

O Br O

26. The major product formed in the following reactions is [JEE MAIN 2018]

O
HI
Heat

OH I

OH I
(A) (B)

OH I

I OH
(C) (D)

27. The major product of the following reaction is [JEE MAIN -(9-1-(M) 2019]

(i) Br2
(ii) EtOH

26
 OEt OEt
OEt

(A) (B)

Br Br
OEt Br

(C) (D)

28. The major product of the following reaction is [JEE MAIN -(9-1-(E) 2019]

O OH
CH3
O AlCl3, 
+

OH OH
H3C CH3

O
O

(B)
(A)

OH OH
CH3

O
(C)
(D)

29. The major product obtained in the following reaction is [JEE MAIN -(9-1-(E) 2019]

OH

(CH3CO)2O/pyridine (1eqv.)
room temp

COCH3
OH OCOCH3

NH2 NH2

(A) (B)
27
 OH

NHCOCH3 NHCOCH3

(C) (D)

30. The major product of the following reaction is [JEE MAIN -(10-1-(E) 2019]

CH3

OH
(i) aq.NaOH
(ii) CH3I

CH3 CH3
CH3 CH3
OH OCH3
OH OH

CH3 CH3 (D)

(C)
(A) (B) CH3

31. Which is the most suitable reagent for the following transformation? [JEE MAIN -(10-1-(E) 2019]

OH
|

CH3 − CH = CH − CH2 − CH3 →

CH3 − CH = CH − CH2CO2 H
(A) alkaline KMnO4 (B) I 2 / NaOH (C) Tollen’s reagent (D) CrO2 / CS2

OH
|
CH3CH2 − C − CH3 cannot be prepared by
32. [JEE MAIN -(12-1-(M) 2019]
|
Ph

(A) HCHO + PhCH (CH3 ) CH2MgX (B) PhCOCH2CH3 + CH3MgX

(C) PhCOCH3 + CH3CH2MgX (D) CH3CH2COCH3 + PhMgX

33. An organic compound ‘X’ showing the following solubility profile is [JEE MAIN -(8-4-(M) 2019]

water
Insoluble
'x'
5% HCl
Insoluble

10% NaOH
Soluble

10% NaHCO3
Insoluble

(A) m-Cresol (B) Oleic acid (C) o-Toluidine (D) Benzamide

28
34. The major product of the following reactions: [JEE MAIN -(8-4-(M) 2019]

OCH3
Conc HBr (excess)
heat

CH=CH2

OH Br
Br OH

(A) (B) (C) (D)

CH2CH2Br Br-CHCH3
CH2CH2Br Br-CHCH3

35. The major product of the following reaction is [JEE MAIN -(9-4-(M) 2019]

1. PBr3
OH
2. KOH (alc.)

OH

O HO HO
(B) (C) (D)
O (A)

36. The major product of the following reaction is [JEE MAIN -(9-4-(M) 2019]

CH3CH = CHCO2CH3 ⎯L⎯iAlH⎯4→

(A) CH3CH2CH2CHO (B) CH3CH = CHCH2OH
(C) CH3CH2CH2CO2CH3 (D) CH3CH2CH2CH2OH
37. The major product of the following reaction is [JEE MAIN -(9-4-(E) 2019]

OH

CH2OH
H2SO4(cat.)
CHCl3
CO2Et

OH O

(A) (B)
OEt
COOH
O

29
 OH O

(C) (D)
O
CO2Et
O

38. p-Hydroxybenzophenone upon reaction with bromine in carbon tetrachloride gives

[JEE MAIN -(9-4-(E) 2019]

Br O
O
Br
(B)
(A)

HO
HO

O O

Br Br
(C) (D)

HO HO

39. The major product of the following reaction is [JEE MAIN -(10-4-(M) 2019]

O
HI(excess)

NC O

OH I OH I
(A) (B) (C) (D)

NC NC OH NC OH NC I
I
40. What will be the major product when m-cresol is reacdted with propargyl bromide
( HC  C − CH2 Br ) in present of K2CO3 in acetone [JEE MAIN -(12-4-(E) 2019]

OH OH
OH O

H3C H3C H3C

CH3 CH3
(A) (B) (C) (D)

30
41. Heating of 2-chloro-1-phenylbutane with EtOK/EtOH gives X as the major product. Reaction of X with
Hg (OAc )2 / H2O followed by NaBH4 gives Y as the major product. Y is [JEE MAIN -(12-4-(E) 2019]

OH OH

(A) Ph (B) Ph (C) Ph (D) Ph

OH
42. 1-methyl ethylene oxide when treated with an excess of HBr produces: [JEE MAIN -(7-1-(M) 2020]

Br Br
(A ) CH3 Br
(B ) (C ) B r (D ) B r
CH3 Br
CH3
43. Arrange the following compounds in increasing order of C-OH bond length: [JEE MAIN -(8-1-(M) 2020]
methanol, phenol, p-ethoxyphenol
(A) phenol < methanol < p-ethoxyphenol (B) phenol < p-ethoxyphenol < methanol
(C) methanol < p-ethoxyphenol < phenol (D) methanol < phenol < p-ethoxyphenol

44. The majoor product of the followig reaction is [JEE MAIN -(8-1-(M) 2020]

OH
dil.H2SO4

OH CH3
H3C
(A) (B)
H3C OH
OH
OH
H 3C

CH3
H3C OH
OH
(C)
(D)
OH H3C
HO CH3
H3C CH3

45. Among the compounds A and B with molecular formula C9 H18O3, A is having higher boiling point the B.
The possible structures of A and B are [JEE MAIN -(8-1-(E) 2020]

A=HO OH

HO

31
 B=H3CO OCH3 A=H3CO OCH3

(A)

OCH3 OCH3

B=HO
OH A=H3CO OCH3
(B)

OH
OCH3

B=HO OH A=HO OH
(C)

HO
HO

B=HO
OH
(D)

OH

JE E - M A I N A N SW ER K EY ALCOH OL, PH E N O L &

Que. 1 2 3 4 5 6 ETH
7 ER 8 9 10
Ans. C B D B D D C B D D
Que. 11 12 13 14 15 16 17 18 19 20
Ans. C D C B A C B B D B
Que. 21 22 23 24 25 26 27 28 29 30
Ans. A C B D C D D A C D
Que. 31 32 33 34 35 36 37 38 39 40
Ans. B A A D D B C D C D
Que. 41 42 43 44 45
Ans. D D B B A

32
 Page-33

Alcohol, Phenol & Ether (IIT Adv.)

OH

NaOH(aq)/Br2
1. In the reaction the intermediate(s) is (are)

_
O O O_ O_
Br

(A) (B) (C) (D)

Br
Br Br Br
Br
[+3, -1] [JEE – 2010]

2. Identity the binary mixture(s) that can be separated into individual compounds, by differential
extraction, as shown in the given scheme. [+4, 0] [JEE-2012]

NaOH(aq)
Compound 1 + Compound 2
Binary mixture containing
Comound 1 and compound 2
NaHCO3(aq)
Compound 1 + Compound 2

(a) C6H5OH and C6H5COOH (b) C6H5COOH and C6H5CH 2OH

(c) C6H5CH2OH and C6H5OH (d) C6H5CH2OH and C6H5CH2COOH

3. The major product(s) of the following reaction is(are) [+3, -1][JEE-2013]

OH

aqueous Br2 (3.0 equivalents)

?

SO3H
OH OH OH
OH
Br Br Br
Br Br

Br Br Br
Br Br
SO3H SO3H
Br Br
P Q R S
(A) P (B) Q (C) R (D) S
 Page-34

4. In the following reaction, the product(s) formed is(are) [+3, -1][JEE-2013]

OH

CHCl3
?
OH

CH3
OH O OH OH
OHC CHO CHO

CH3 H3C CHCl2 H3C CHCl2 CH3

P Q R S
(A) P (major) (B) Q (minor) (C) R (minor) (D) S (major)

5. The reactivity of compound Z with different halogens under appropriate conditions is given
below: [3, 0][JEE-2014]
mono halo substituted derivative when X2 = I2
OH

X2
di halo substituted derivative when X2 = Br2

Z C(CH3)3 tri halo substituted derivative when X2 = Cl2

The observed pattern of electrophilic substitution can be explained by
(A) The steric effect of the halogen
(B) The steric effect of the tert-butyl group
(C) The electronic effect of the phenolic group
(D) The electronic effect of the tert-butyl group
6. The acidic hydrolysis of ether (X) shown below is fastest when [+3, -1][JEE-2014]

acid
OR OH + ROH

(A) One phenyl group is replaced by a methyl group.

(B) One phenyl group is replaced by a para-methoxyphenyl group.
(C) Two phenyl group are replaced by two para-methoxyphenyl groups.
(D) No structural change is made to X.
 Page-35

7. The number of hydroxyl group(s) in Q is [+4, 0] [JEE-2015]

H H aqueous dilute KMnO4(excess)

P Q
heat 00C

HO
H3C CH3

8. The major product U in the following reactions is [+4, -2] [JEE – 2015]

CH2 = CH CH3,H radical initiator,O2

T U
high pressure, heat

O H3C CH3
O
O

CH3
O H

(A) (B)
H

CH2
O O
O H

CH2
O

(C) (D)

9. The correct statement(s) about the following reaction sequence is(are)

i) O2 CHCl3 / NaOH
Cumene(C9H12) P Q (major) + R ( minor)
ii) H3O+

NaOH
Q S
PhCH2Br

[+4, -2] [JEE – 2016]

(A) R is steam volatile
(B) Q gives dark violet coloration with 1% aqueous FeCl3 solution
(C) S gives yellow Precipitate with 2, 4- dinitrophenylhydrazine
 Page-36

(D) S gives dark violet coloration with 1% aqueous FeCl3 solution

10. Reagent(s) which can be used to bring about the following transformation is(are)

O O
O O
C OH
C O

H O
O
COOH
COOH [+4, -2] [JEE – 2016]
(A) LiAlH4 in (C2H5)2O (B) BH3 in THF
(C) NaBH4 in C2H5OH (D) Raney Ni / H2 in THF

11. LIST –I contains reactions and LIST-II contains major products.

[+3, 0] [JEE – 2018]

Match each reaction in List –I with one or more products in List –II and choose the correct option.
(A) P→1,5; Q→2; R→3; S→4 (B) P→1, 4; Q→2; R→4; S→3
(C) P→1, 4; Q→1, 2; R→3, 4; S→4 (D) P→4, 5; Q→4; R→4; S→3, 4

ANSWER KEY

1. (ABC) 2. (BD) 3. (b) 4. (BD) 5. (ABC) 6. (C) 7. (4)

8. (B) 9. (BC) 10. (CD) 11. (B)