Date Planned : __ / __ / __ Daily Tutorial Sheet-1 Expected Duration : 30 Min

Actual Date of Attempt : __ / __ / __ Level-1 Exact Duration :_________

1. Denatured alcohol is :
(A) ethanol + methanol (B) rectified spirit + methanol + naphtha
(C) undistilled ethanol (D) rectified spirit

2. Hydroboration oxidation of 4-Methyloct-4-ene would give :

(A) 5-Methyloctan-4-ol (B) 4-Methyloctan-4-ol
(C) 4-Methylheptanol (D) 4-Methyl-2-octanone

3. Which among the following compounds can give a secondary alcohol on reacting with Grignard reagent
followed by acid hydrolysis ?
I. HCHO II. C 2H5CHO
III. CH3COCH3 IV. HCOOC2H5
Select the correct answer using the codes given below :
(A) II only (B) III only (C) I and IV only (D) II and IV only

4. Acid catalysed hydration of alkenes except ethene leads to the formation of :

(A) mixture of secondary and tertiary alcohols
(B) mixture of primary and secondary alcohols
(C) secondary or tertiary alcohol
(D) primary alcohol

5. The enzymes which are used to convert starch into ethyl alcohol are :
(A) maltase, diastase (B) diastase, maltase, zymase
(C) invertase, zymase (D) invertase, diastase, maltase

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

(A) CH3MgI and CH3COCH3 (B) CH3MgI and C2H5OH
(C) CH 3MgI and CH 3COOC 2H5 (D) CH3 MgI and HCHO

7. In fermentation by zymase, alcohol and CO2 are obtained from :

(A) invert sugar (B) glucose (C) fructose (D) All of these
X
8. R  CH  CH  CH 2  CHO 
 R  CH  CH  CH 2  CH 2OH
In the above sequence X can be :
(A) H2 / Ni (B) LiAlH4/ether (C) K 2Cr2O7 / H (D) Both (A) and (B)

9. The alcohol manufactured from water gas is :

(A) CH 3OH (B) C 2H5 OH (C) CH 3CH 2COOH (D) (CH 3 )2 CHOH

10. Cyclohexanol on reaction with PBr3 in presence of pyridine gives :

(A) Bromocyclohexene (B) Bromocyclohexane
(C) 1-Bromocyclohexanol (D) None of these

Level-1 | DTS-1 79 Oxygen Containing Organic Compounds-I

11. Amongst the following alcohols, the one that would react fastest with conc. HCl and anhydrous ZnCl2 is :
(A) 2-Butanol (B) 2-Methylpropan-2-ol
(C) 2-Methylpropan-1-ol (D) 1-Butanol

12. RCH2 CH 2OH can be converted into RCH 2CH2COOH by the following sequence of steps :

(A) PBr3 , KCN, H 3O  (B) PBr3 , KCN, H 2 / Pd


(C) KCN, H3O (D) KCN, PBr3 , H3O 

13. Which compound will have highest boiling point ?

(A) CH 4 (B) CH3OH (C) C2H5OH (D) HCHO

14. The function of ZnCl2 in Lucas test for alcohols is :

(A) To act as acid catalyst (B) To act as base catalyst
(C) To act as amphoteric catalyst (D) To act as neutral catalyst

15. The correct order of reactivity of hydrogen halides with ethyl alcohol is :
(A) HF > HCl > HBr > HI (B) HCl > HBr > HF > HI
(C) HBr > HCl > HI > HF (D) HI > HBr > HCl > HF

Level-1 | DTS-1 80 Oxygen Containing Organic Compounds-I

 Date Planned : __ / __ / __ Daily Tutorial Sheet-2 Expected Duration : 30 Min
Actual Date of Attempt : __ / __ / __ Level-1 Exact Duration :_________

16. Consider the following reaction, C2H5OH  H2SO4  Product

Among the following, which one cannot be formed as a product under any conditions ?
(A) Ethyl hydrogen sulphate (B) Ethylene
(C) Acetylene (D) Diethyl ether

17. In the given sequence of reactions :

2 P I Mg2 HCHO H O
CH3CH2OH   A 
 B  C  D the compound ‘D’ is :
ether

(A) Butanal (B) n-Butyl alcohol

(C) n-Propyl alcohol (D) Propanal

2 4 conc.H SO
18. The major product of the following reaction C6H5CH2CH(OH)CH(CH3 )2   is :


(A) (B)

(C) (D)

19. An organic compound ‘X’ on treatment with pyridinium chloro chromate in dichloromethane gives
compound ‘Y’. The compound ‘Y’, reacts with I2 and alkali to form tri-iodomethane. The compound ‘X’ is:
(A) C 2H5 OH (B) CH3 CHO (C) CH 3OH (D) CH3COOH

20. 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 FeCl 3
21. An unknown compound ‘D’ first oxidised to aldehyde and then acetic acid by a dilute solution of
K 2Cr2O7 and H2 SO 4 . The compound ‘D’ is :
(A) CH3OH (B) C2H5OH
(C) CH3CH2COOH (D) CH3CH2CHO

Oxidation
3 NH
22. In the reaction, CH3OH 
 A  B; A and B are :
(A) HCHO, HCOONH 4 (B) HCOOH, HCOONH 4
(C) HCOOH, HCONH2 (D) HCHO, HCONH2

23. Which of the following will not react with an aqueous solution of NaOH ?

(A) (B) C2H5OH

(C) CH3CONH2 (D) CH(CN)3

Level -1 | DTS-2 81 Oxygen Containing Organic Compounds-I

 Re flux
24.  X. What is X ?
2-Propanol  NaBr 
Acid

(A) 2-Bromopropane (B) Propane

(C) Propene (D) Propanone

25. Which of the following compounds is most acidic ?

(A) CH 4 (B) C 2H 6 (C) CH  CH (D) C 2H5 OH

26. Tertiary alcohols having at least four carbon atoms upon drastic oxidation yield carboxylic acid with :
(A) one carbon atom less (B) two carbon atoms less
(C) three carbon atoms less (D) All the above three options are correct

27. Consider the following reactions :

Anhydrous AlCl
3 ahydrous ZnCl /HCl
2
X  HCl   C2H5Cl 
  Y.
addition  (substitution )

Y can be converted to X on heating with….. at ….. temperature.

(A) Al 2O3 , 350 C (B) Al 2 O3 , 200C

(C) MCPBA (m-chloroperoxobenzoic acid) (D) NaOH/ I2, 60 C

28. Two aromatic compounds having formula C7H8O which are easily identifiable by FeCl 3 solution test
(violet colouration) are :
(A) o-cresol and benzyl alcohol (B) m-cresol and p-cresol
(C) o-cresol and p-cresol (D) methylphenylether and benzyl alcohol

Reaction Reaction
29. Chlorobenzene  Phenol  Salicyldehyde. The reactions X and Y are respectively :
X Y

(A) Fries rearrangement and Kolbe-Schmidt

(B) Cumene and Reimer-Tiemann
(C) Dow’s process and Reimer-Tiemann
(D) Dow’s process and Friedel-Craft
X
30.  forms a mono-bromo derivative. “X” is :
Phenol 

(A) bromine in benzene (B) bromine in water

(C) potassium bromide solution (D) bromine in carbon disulphide at 0°C

Level-1 | DTS-2 82 Oxygen Containing Organic Compounds-I

 Date Planned : __ / __ / __ Daily Tutorial Sheet-3 Expected Duration : 30 Min
Actual Date of Attempt : __ / __ / __ Level-1 Exact Duration :_________

31. Phenol is heated with a solution of mixture of KBr and KBrO3 in presence of HCl. The major product
obtained in the above reaction is :
(A) 2-Bromophenol (B) 3-Bromophenol
(C) 4-Bromophenol (D) 2, 4, 6-Tribromophenol

32. To distinguish between salicylic acid and phenol one can use :
(A) NaHCO3 solution (B) 5% NaOH solution
(C) neutral FeCl3 (D) bromine water

33. In the reaction for dinitration The major di-nitrated product X is :

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

34. An organic compound ‘X’ with molecular formula, C7 H8O is insoluble in aqueous NaHCO3 but dissolves
in NaOH. When treated with bromine water, ‘X’ rapidly gives ‘Y’ with molecular formula C7H5OBr3.
The compounds ‘X’ and ‘Y’ respectively, are :
(A) Benzyl alcohol and 2, 4, 6-Tribromo-3-methoxybenzene
(B) Benzyl alcohol and 2, 4, 6-Tribromo-3-methylphenol
(C) m-cresol and 2, 4, 6-Tribromo-3-methylphenol
(D) Methoxybenzene and 2, 4, 6-Tribromo-3-methoxybenzene

35.

P is :

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

36. Which of the following compound would not evolve CO2 when treated with NaHCO3 solution ?
(A) Salicylic acid (B) Phenol
(C) Benzoic acid (D) 4-Nitrobenzoic acid

Level-1 | DTS-3 83 Oxygen Containing Organic Compounds-I

37. The major product of the given reaction is :

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

38. Phenol is more acidic than alcohol because :

(A) phenol is more soluble in polar solvents (B) alcohol does not loose hydrogen atom
(C) phenoxide ion is stabilised by resonance (D) phenoxide ion doesn’t exhibit resonance

39. When benzene sulphonic acid and p-nitrophenol are treated with NaHCO 3 , the gases released
respectively are :
(A) SO2, NO2 (B) SO2, NO (C) SO2, CO2 (D) CO2, CO2

40. Which one of the following compounds will not react with CH3MgBr ?
(A) Ethylacetate (B) Acetone (C) Dimethylether (D) Ethanol

41. The boiling point of ethanol (molecular weight = 46) is 78°C, what can be the boiling point of diethyl
ether? (Molecular weight = 74)
(A) 100°C (B) 78°C (C) 86°C (D) 34°C

42. The products obtained when Benzyl phenyl ether is heated with HI in the mole ratio 1 : 1 are :
1. Phenol 2. Benzyl alcohol 3. Benzyl iodide 4. Iodobenzene
The correct choice is :
(A) 1 and 3 only (B) 3 and 4 only (C) 1 and 4 only (D) 2 and 4 only

43.

The product is :

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

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

(A) passing ethanol over heated alumina at 350 C
(B) heating sodium ethoxide with ethyl bromide
(C) treating ethyl alcohol with excess of H 2SO 4 at 430-440K
(D) heating ethanol with dry Ag 2O

45. Phenol undergoes electrophilic substitution more easily than benzene because :
(A) OH group exhibits  M effect and hence increase the electron density on the o- and p-positions

(B) Oxocation is more stable than the carbocation

(C) Both A and B
(D)  OH group exhibits acidic character

Level-1 | DTS-3 84 Oxygen Containing Organic Compounds-I

 Date Planned : __ / __ / __ Daily Tutorial Sheet-4 Expected Duration : 30 Min
Actual Date of Attempt : __ / __ / __ Level-1 Exact Duration :_________

46. One mole of an organic compound A with the formula C 3H 8O reacts completely with two moles of HI to
form X and Y. When Y is boiled with aqueous alkali, it forms Z. Z gives the iodoform test. The compound
A is :
(A) Propan-2-ol (B) Propan-1-ol (C) Ethoxyethane (D) Methoxyethane

47. Tert-butyl methyl ether on heating with hot conc. HI gives :

(A) CH3OH  (CH3 )3 CCl (B) CH3I  (CH3 )3 COH
(C) CH 3I  (CH3 )3 CCl (D) CH 3 OH  (CH3 )3 C  I

48. A, A is :

(A) CH3 C HC H2OH (B) CH 3CH 2CH2CH 2OH

|
CH 3
CH3
|
(C) CH3 C  OH (D) No reaction
|
CH3

49. To prepare phenyl t-butyl ether, best synthesis is :

(A) (B)

(C) (D) None of the above is suitable

50. Which of the following paths will provide a better synthesis of ether ?

I. II.

(A) I (B) II
(C) Of equal importance (D) None of these

51. Glycerol reacts with potassium bisulphate to produce :

(A) allyl iodide (B) allyl sulphate
(C) acryl aldehyde (D) glycerol trisulphate

52. The product formed when glycerol reacts with PCl5 is:
(A) 1, 2, 3-trichloropropane (B) glycerol monochlorohydrin
(C) glycerol dichlorohydrin (D) All of these

Level-1 | DTS-4 85 Oxygen Containing Organic Compounds-I

53. Consider the following reactions

The product (C) is:

(A) (B)

(C) (D)

54. . P is :

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

55. .

Final product B in above sequence of reaction is :

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

56. In the given reaction :

OH OH
| | HIO4
CH3  C H  C  CH3   (P)  (Q)
|
CH3
(P) and (Q) respectively be :
(A) CH3CHO and CH3CHO (B) CH3COCH3 and CH3CHO
(C) CH3COCH3 and CH3COCH3 (D) CH3COOH and CH3COCH3

*57. Which is(are) correct statements ?

(A) Oxidation product of 1, 2-Ethanediol with HIO 4 is formaldehyde
(B) 1° alcohol turns K 2Cr2O7 / H solution green
(C) t-Butyl alcohol is converted to isobutene on heating with Cu
(D) CH3OH is also called wood spirit

Level-1 | DTS-4 86 Oxygen Containing Organic Compounds-I

*58. Identify A and B.
HIO
4  2CH CHO  HCOOH
A  3
2 mol
HIO
4
B   HOOC  (CH2 )4  CHO
1 mol

The correct options are :

(A) A is : CH3  CH  CH  CH  CH 3 (B) A is : CH2  CH  CH  CH2  CH3
| | | | | |
OH OH OH OH OH OH
O
||
(C) B is : (D) B is : CH2  CH  (CH2 )4  C  CH2
| | |
OH OH OH
59. In which of the following reaction, the product is an ether ?
(A) C6H6  CH3COCl/ anhydrous AlCl 3 (B) C2H5Cl  aq. KOH
(C) C 6 H6  C6 H5 COCl / anhydrous AlCl3 (D) C 2H5Cl  C 2H5 ONa

60.

(A) (B)

(C) (D)

Level-1 | DTS-4 87 Oxygen Containing Organic Compounds-I

 Date Planned : __ / __ / __ Daily Tutorial Sheet-5 Expected Duration : 30 Min
Actual Date of Attempt : __ / __ / __ Level-1 Exact Duration :_________

61.

The product is :

(A) (B)

(C) (D)

62.

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

63. Ethanol on reaction with acetic anhydride gives :

(A) Acetic ester (B) Formic ester
(C) Ethanoic acid (D) Both acetic ester and ethanoic acid

64. The major product is :

(A) (B) (C) Both (A) and (B) (D) None is correct

65. Methanol and water can be separated from a mixture by :

(A) distillation (B) fractional distillation
(C) evaporation (D) separating funnel

66. An alcohol gave Lucas test in about 15 minutes. When the alcohol was treated with hot concentrated
H2SO 4 it gave an alkene of molecular formula C4 H8 which on ozonolysis gave C2H4O. The structure of
alcohol is :
(A) CH3CHOHCH2CH3 (B) CH3CH2CH2CH2OH
(C) CH 3CHOHCH2 CH 2CH 3 (D) (CH 3 )3 C  OH

Level-1 | DTS-5 88 Oxygen Containing Organic Compounds-I

67.

Sum of number of alcoholic groups in product (P) and (Q) is :

(A) 1 (B) 2 (C) 3 (4) 5

68. Thiols are alcohol analogs in which the oxygen has been replaced by sulphur (e.g. CH 3SH). Given the
fact that the S  H bond is less polar than the O  H bond, which of the following statements comparing
thiols and alcohols is correct ?
(A) Hydrogen bonding forces would be the same
(B) Hydrogen bonding forces are stronger in thiols
(C) Hydrogen bonding forces are weaker in thiols
(D) No comparison can be made without additional information

69. What is the major organic product of the following sequence of reactions ?

OH OH
| |
(A) (CH3 )2 CH C H CH 2CH3 (B) (CH3 )2 CHCH2 C H CH 3
(C) (CH3 )2 CHCH2CH2OH (D) (CH3 )2 CHCH2CH2CH2OH

*70. An organic compound B is formed by the reaction of ethyl magnesium iodide (CH3CH 2MgI) with a
substance A, followed by treatment with dilute aqueous acid. Compound B does not react with PCC or
PDC in dichloromethane. Which of the following can be possible structures of A ?
O O
|| ||
(A) CH3 CH (B) H2C  O (C) (D) CH3CH2 C CH3

X Y
71. CH3CH  CH2   CH3CH2CHO. X and Y are respectively :
 

(A) H3O , MnO4 / H  (B) H3O  , PCC/ CH2Cl2

(C) BH3  THF / H 2O2, OH , H2CrO 4 (D) BH3  THF / H 2O2, OH , PCC /CH 2Cl2

72. The structure of the compound that gives a tribromo derivative on reaction with bromine water is :

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

Level-1 | DTS-5 89 Oxygen Containing Organic Compounds-I

73. Indicate the reagent in the following conversion

(A) H / CH3OH (B) CH3ONa

(C) Hg(OAc)2, CH3OH (D) None of these

74.

The product are :

(A) (B) via SN1

(C) via SN2 (D)

CH MgBr (2.0 eq.)

3 3 H O
*75. 
 

The products formed in above reaction are :

O OH OH OH
|| | | |
(A) CH3  C  CH2  CH2  C  CH3 (B) CH3  C  CH2  CH2  C  CH3
| | |
CH3 CH3 CH3

O O
|| ||
(C) CH3  C  CH2  CH2  C  CH3 (D) HOCH2CH2OH

Level-1 | DTS-5 90 Oxygen Containing Organic Compounds-I

 Date Planned : __ / __ / __ Daily Tutorial Sheet-6 Expected Duration : 30 Min
Actual Date of Attempt : __ / __ / __ Level-2 Exact Duration :_________

76. Rate of hydration of

will be in order :
(A) I < II < III (B) I < III < II (C) II < I < III (D) III < II < I

*77. 3-Methyl-3-hexanol can be prepared by :

(A) CH3MgI and 3-Hexanone, followed by hydrolysis
(B) C 2H5 MgI and 2-Pentanone, followed by hydrolysis

(C) n-Pr-MgI and 2-Butanone, followed by hydrolysis

(D) n-Bu-MgI and Propanone, followed by hydrolysis

CHO
| 2HIO4
78. C H  OH  Products obtained in the reaction are :
|
CH2 OH

(A) HCHO,HCO2H (B) HCHO,2HCO2H

(C) CO2,2HCO2H (D) CO2,HCHO,HCO2H

CHO CH2OH
| | 5HIO4
4HIO4
79. (i) (C H  OH)3  Product (ii) (C H  OH)4  Product
| |
CH2 OH CH2 OH
Ratio of moles of formic acid obtained in reaction (i) and reaction (ii) is :
(A) 3/4 (B) 4/5 (C) 1 (D) 5/4

80. Cyclobutylethene is treated with dil. H2SO4 and boiled with water to form :
(A) 2-Cyclobutylethanol (B) 1-Cyclobutyl-2-ethanol
(C) 2-Methylcyclopentanol (D) 1-Methylcyclopentanol

2 H O 2 4 dil. H SO
2 H
*81. In the reaction sequence, CaC2  A   B   C.
HgSO4 Ni

True statement about the product C is :

(A) Give yellow ppt. with NaOI (B) Its oxidation product is carbonyl compound
(C) Its oxidation product is CO2 and H2O (D) Its oxidation product is CH3COOH

*82. Which of the following alcohol(s) can be oxidised by KMnO 4 / H  ?

(A) Ethanol (B) Tert-butylalcohol
(C) Isopropyl alcohol (D) Allyl alcohol

Level-2 | DTS-6 91 Oxygen Containing Organic Compounds-I

*83. Which of the following compound(s) gives alcohol on reaction with LiAlH4 / H2O ?
(A) Me  C  Cl (B) Me  C  NH2 (C) (D) Me  C  O  C  Me
|| || || ||
O O O O
*84. End-product of which of following reactions gives positive Iodoform test ?
O O
|| (i) CH3 MgBr (excess) || (i) CH3 MgBr (excess)
(A) H  C  Cl    (B) Ph  C  O  Et   
(ii) H (ii) H

O O
|| (i) CH3 MgBr (excess) || (i ) CH3 MgBr (excess)
(C) H  C  O  Et    (D) CH 3  C  H   
(ii) H (ii ) H

*85. Which of the following reactions represents the correct product ?

(A) (B)

(C) (D)

Level-2 | DTS-6 92 Oxygen Containing Organic Compounds-I

 Date Planned : __ / __ / __ Daily Tutorial Sheet-7 Expected Duration : 30 Min
Actual Date of Attempt : __ / __ / __ Level-2 Exact Duration :_________

86. Dehydration of the alcohols

will be in order :
(A) IV > II > III > I (B) I > II > III > IV (C) IV > II > III > I (D) II > IV > I > III

87. When o- or p-Phenolsulphonic acid is treated with bromine water, the product formed is :
(A) 2, 4-Dibromophenol (B) 2, 4, 6-Tribromophenol
(C) 3-Bromophenol (D) 3, 5-Dibromophenol

*88.

Identify correct combination :

CH2 OH
(A) (A )  | (B) (B)  LiAlH4 / Ether
CH2 SH

(C) (C)  KMnO4 (D) (D)  H3O

89. Product

The product formed in the above reaction is :

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

O O
|| H ||
90. 
R  C  O  H  R1  OH   R  C  O  R1
In above esterification reaction, the rate of reaction is maximum, when R1  OH is :
(A) 1° alcohol (B) 3° alcohol
(C) 2° alcohol (D) CH3OH

Level-2 | DTS-7 93 Oxygen Containing Organic Compounds-I

91. A and B in the given reaction are :
4KMnO 4 KMnO / OH 
B 
  (CH3 )3 COH  A
H ,
(A) A and B both are (CH 3 )2 C  CH2
(B) A and B both are (CH 3 )2 CO  CH2O
(C) A is (CH3 )3 COH while B is (CH3 )2 C  CH2 or (CH3 )2 CO
(D) A and B both are (CH3 )3 COH, i.e., there is no reaction

*92. Which of the following statement(s) is(are) true ?

(A) All alcohols are weaker acids than water except methanol
(B) All alcohols are stronger acid than water
(C) All alcohols are much weaker acids than terminal alkynes
(D) All alcohols are stronger acids than terminal alkynes

*93.

(A) X is (B) Y is

(C) Z is (D) Z is

*94. Lucas test is used to make distinction between 1°, 2° and 3° alcohols
2 ZnCl
ROH + HCl  RCl  + H2O
conc. anhydrous White turbidity
This shows that
(A) ROH behaves as a base.
(B) greater the value of pK a (alcohol), greater the reactivity with conc. HCl and thus sooner the
formation of white turbidity.
(C) alcohol which reacts fastest with Na metal, will give turbidity at fastest rate.
(D) alcohol which gives red colour during Victor Meyer test, will always give turbidity at slower rate
than those giving blue or white colour during Victor Meyer test.

*95. :

Which of the following are possible products in the above reaction ?

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

Level-2 | DTS-7 94 Oxygen Containing Organic Compounds-I

 Date Planned : __ / __ / __ Daily Tutorial Sheet-8 Expected Duration : 30 Min
Actual Date of Attempt : __ / __ / __ Level-2 Exact Duration :_________

96.

Product (C) is ?

(A) (B)

(C) (D)

97. What product(s) are expected from the following reaction ?

(A) 2CH3CH2I (B) 2 HOCH2CH2OH
(C) 2CH2ICH 2I (D) CH 3CH 2I  CH 3CH2OH

H
98. ; A 
 B. B is :
Catalysis

(A) (B) (C) HCHO (D) CH3 CHO

99. Acetal formation is a reversible reaction :

Under what conditions, the reaction can be forced to proceed only in right (forward) direction ?
(A) Using excess of alcohol (B) Using high temperature
(C) Using dilute acid and excess of alcohol (D) Using dry acid and excess of alcohol

100.


The product (C) is :

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

Level-2 | DTS-8 95 Oxygen Containing Organic Compounds-I

*101. By which of the following procedures ethyl-n-propylether is obtained as product ?
HI Mg H O
2  III  1. Na
(A) C2H5OH  I 
 II   Product
ether 2.CH3CH2Br
HBr Mg2  1. CH O 1. Na
(B) C2H5OH  I 
 II 
  III  Product
ether 2. H3O 2. CH3CH2Br
140C
(C) C2H5OH  H2SO4 
 Product
140
(D) C2H5OH  CH3CH2CH2OH  H2 SO4 
 Product

1. NaOH H  /H O
2  B 
2 C Ac O
102. Phenol 
 A 
2.CO2 /130C

In this reaction, the end product C is :

(A) salicyldehyde (B) salicylic acid
(C) phenyl acetate (D) aspirin

*103. Which of the following reactions will yield p-tert butylphenol ?

CH3
| H H
(A) Phenol  CH3  C  CH2  (B) Phenol  (CH3 )3 COH 
AlCl
3
(C) Phenol  (CH3 )3 CCl   (D) None of these

H
*104. The reaction 2CH3CH2OH  CH3CH2OCH2CH3 is believed to occur through the formation of :
413 K
 
(A) CH3CH2 OH2 (B) CH3 CH2

(C) CH3CH2  O CH2CH3 (D) None of these
|
H
105. Match The Column :
Column - I Column - II

(A) (p) White turbidity with ZnCl 2 / HCl

(B) CH 3CH 2OH (q) Violet colour with FeCl 3

OH
|
(C) Ph  C H  CH3 (r) Colour change of Na 2Cr2O7 / H 

(D) (CH3 )3 C  OH (s) I2 / OH gives bright yellow precipitate

(t) Soluble in NaOH

Level-2 | DTS-8 96 Oxygen Containing Organic Compounds-I

 Date Planned : __ / __ / __ Daily Tutorial Sheet-9 Expected Duration : 30 Min
Actual Date of Attempt : __ / __ / __ Level-2 Exact Duration :_________

106.

The product (A) will be :

(A) (B)

(C) (D) None of these

107.

Sum of x and y is :
(A) 2 (B) 3 (C) 4 (D) 5

108.

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

HI (conc.)
109. Me2CHOCMe3  X  Y


Predict the nature of product and the type of reaction involved in their formation :
(A) Me2CH  I and Me3COH, formed by S N1 reaction

(B) Me2CHOH and Me3C  I, formed by SN1 reaction

(C) Me2CH  I and Me3COH, formed by S N 2 reaction

(D) Me2CHOH and Me3C  I, formed by S N 2 reaction

Level-2 | DTS-9 97 Oxygen Containing Organic Compounds-I

110. The final product (IV) in the sequence of reactions is :

OH
|
(A) CH3  CHOCH2CH2OH (B) CH3  CH CHCH3
| |
CH3 CH3

(C) CH3  CH  CH2CH2OH (D) CH3  CHOCH2CH3

| |
CH3 CH3

111. The product is :

(A) CH2  CH  C2H5 (B) C2H5  CH  CH2CH3

| | |
OH CH3 OH

(C) C2H5  CH2  CH  CH3 (D) C2H5  CH  CH  CH3

|
OH

*112. Which of the following is(are) true for the above reaction ?

(A) The products are PhOH  PhCH2OH (B) The products are PhOH  PhCH2I
(C) The reaction path is via S N 2 (D) The reaction path is via SN1

*113. Cyclopentylether can be obtained by :

(A) (B)

(C) (D)

*114. Diethylether reacts with PCl5 to form :

(A) Ethylchloride (B) Phosphorousoxytrichloride
(C) 1, 2-Dichloroethane (D) Ethene
 
115. Consider the following reaction : R O N a  R  X  R  O  R   NaX
Which of the following statement is/are correct ?
(A) The reaction is called Williamson’s synthesis.
(B) It is a nucleophillic substitution reaction
(C) The reaction is applicable to all types of alkyl halides
(D) If R'X is a primary alkyl halide, the reaction proceeds through S N 2 mechanism

Level-2 | DTS-9 98 Oxygen Containing Organic Compounds-I

 Date Planned : __ / __ / __ Daily Tutorial Sheet-10 Expected Duration : 30 Min
Actual Date of Attempt : __ / __ / __ Level-2 Exact Duration :_________

116. Which can be cleaved by HIO4 ?

O O HO O
  | ||
(A) CH3CH2 C CH 2 C CH3 (B) CH3 CH C CH2CH 3
O O
|| ||
(C) (D) CH3 C CH2 CH CH2 CCH3
|
OH

117. x is moles of HIO4 consumed :

(A) x 3 (B) x 2 (C) x 4 (D) x 1

118. Which of the following compound gives HCHO, CO 2 and three moles of HCO2 H when oxidized by
periodic acid ?

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

119.

(1) (i) CH3 MgBr (ii) H3O+ (2) KMnO4 (cold dil.)
(3) CrO3 (4) H / 
For the above conversion the correct order of reagents used is :
(A) 1  2  3  4 (B) 1  4  3  2 (C) 1  4  2  3 (D) 2  3  4 1

*120. Which of the following are cleaved by HIO4 ?

(A) Glycerol (B) Glycol (C) 1, 3-Propenediol (D) THF

121.

The major product is :

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

Level-2 | DTS-10 99 Oxygen Containing Organic Compounds-I

*122. Which of the following is correct about the given reaction :

(A) Reactant has four functional groups (B) Product is tetrahydroxy compound
(C) Product has three primary alcohol groups (D) Product can’t be oxidised by MnO2

123.

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

[

*124. Which method is useful synthesis of ether ?

(A)

(B)

(C)

(D) (CH3 )3 CBr  CH3CH2ONa 

125. Match the following :

Column I Column II

(A) (p) Reduction by LiAlH4

(B) (q) Reduction by NaBH4

O

(C) CH3 — C —OH (r) Positive Iodoform

(D) (s) Reacts with Na to evolve H2 gas

Level-2 | DTS-10 100 Oxygen Containing Organic Compounds-I

 Date Planned : __ / __ / __ Daily Tutorial Sheet-1 Expected Duration : 45 Min
Actual Date of Attempt : __ / __ / __ JEE Main (Archive) Exact Duration :_________

1. During dehydration of alcohols to alkenes by heating with concentrated H2SO4 the initiation step is :
(2003)
(A) protonation of alcohol molecule (B) formation of carbocation
(C) elimination of water (D) formation of an ester

2. An ether is more volatile than an alcohol having the same molecular formula. This is due to : (2003)
(A) dipolar character of ethers
(B) alcohols having resonance structures
(C) intermolecular hydrogen bonding in ethers
(D) intermolecular hydrogen bonding in alcohols

3. Among the following compounds which can be dehydrated very easily? (2004)
OH
|
(A) CH 3CH2CH 2CH2CH 2OH (B) CH3CH2CH2 CHCH3
CH3
|
(C) CH3CH2 CCH2CH3 (D) CH3CH2 CHCH2CH2OH
| |
OH CH3

4. The IUPAC name of the compound is : (2004)

(A) 3, 3-dimethyl-1-hydroxy cyclohexane (B) 1, 1-dimethyl-3-hydroxy cyclohexane

(C) 3, 3-dimethyl-1-cyclohexanol (D) 1, 1-dimethyl-3-cyclohexanol
5. For which of the following parameters the structural isomers C 2H5OH and CH3OCH 3 would be expected
to have the same values ? (Assume ideal behaviour) (2003)
(A) Heat of vaporisation (B) Vapour pressure at the same temperature
(C) Boiling points (D) Gaseous densities at the temperature and pressure

6. p-cresol reacts with chloroform in alkaline medium to give the compound A which adds hydrogen cyanide
to form the compound B. The latter on acidic hydrolysis gives chiral carboxylic acid. The structure of the
carboxylic acid is : (2005)

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

7. The best reagent to convert pent-3-en-2-ol into pent-3-en-2-one is : (2005)

(A) acidic permanganate (B) acidic dichromate
(C) chromic anhydride in glacial (D) pyridinium chlorochromate

JEE Main (Archive) | DTS-1 104 Oxygen Containing Organic Compounds-I

8. HBr reacts with CH2  CH  OCH3 under anhydrous conditions at room temperature to give : (2006)
(A) CH3CHO and CH3OH (B) BrCH2CHO and CH3OH
(C) BrCH2  CH2  OCH 3 (D) H3C  CHBr  OCH 3

9.

The electrophile involved in the above reaction is : (2006)


(A) dichloromethyl cation (CH Cl 2 ) (B) dichlorocarbene (  CCl 2)
Θ 
(C) trichloromethyl anion (CCl3 ) (D) formyl cation (CHO)

10. Phenyl magnesium bromide reacts with methanol to give : (2006)

(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

2 P I 2 Mg HCHO H O
11. In the given sequence of reactions, CH3CH2OH   A 
 B  C  D the
ether
compound D is : (2007)
(A) propanal (B) butanal (C) n-butyl alcohol (D) n-propyl alcohol

12. Phenol, when it first reacts with concentrated sulphuric acid and then with concentrated nitric acid,
gives : (2008)
(A) nitrobenzene (B) 2, 4, 6-trinitrobenzne
(C) o-nitrophenol (D) phthalic acid

13. The major product obtained on interaction of phenol with sodium hydroxide and carbon dioxide is :
(2009)
(A) benzoic acid (B) salicylaldehyde (C) salicylic acid (D) phthalic acid

14. From amongst the following alcohols the one that would react fastest with conc. HCl and anhydrous
ZnCl2, is: (2010)
(A) 1-butanol (B) 2-butanol
(C) 2-methylpropan-2-ol (D) 2-methylpropanol
2 4 Conc. H SO
15. The main product of the following reaction is : C6H5CH2CH (OH)CH(CH3 )2   (2010)

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

16. Sodium ethoxide has reacted with ethanoyl chloride. The compound that is produced in this reaction is :
(2011)
(A) diethyl ether (B) 2-butanone
(C) ethyl chloride (D) ethyl ethanoate

17. Phenol is heated with a solution of mixture of KBr and KBrO3. The major product obtained in the above
reaction is : (2011)
(A) 2-bromophenol (B) 3-bromophenol
(C) 4-bromophenol (D) 2, 4, 6-tribromophenol

JEE Main (Archive) | DTS-1 105 Oxygen Containing Organic Compounds-I

18. Ortho-nitrophenol is less soluble in water than p- and m-nitrophenols because : (2012)
(A) o-nitrophenol shows intramolecular H-bonding
(B) o-nitrophenol shows intermolecular H-bonding
(C) melting point of o-nitrophenol is lower than those of m- and p-isomers
(D) o-nitrophenol is more volatile in steam than those of m- and p-isomers

19. Arrange the following compounds in order of decreasing acidity : (2013)

(A) IV > III > I > II (B) II > IV > I > III
(C) I > II > III > IV (D) III > I > II > IV

20. The most suitable reagent for the conversion of R  CH 2  OH  R  CHO is : (2014)
(A) PCC (B) KMnO 4 (C) CrO3 (D) K 2Cr2O7

JEE Main (Archive) | DTS-1 106 Oxygen Containing Organic Compounds-I

 Date Planned : __ / __ / __ Daily Tutorial Sheet-2 Expected Duration : 45 Min
Actual Date of Attempt : __ / __ / __ JEE Main (Archive) Exact Duration :_________

21. Consider the reaction sequence below : (2016)

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

22. The product of the reaction given below is : (2016)

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

23. In the following reaction sequence (2017)

KOH (aq.) ( i) CH3 MgBr Anhy. ZnCl2  Conc. HCl
I  II 
   III 
 gives turbidity immediately
(C3 H6Cl2 ) (ii) H2O /H

The compound I is :
Cl
|
(A) CH2  CH  CH3 (B) CH3  C  CH3
| | |
Cl Cl Cl
(C) Cl  CH  CH2  CH3 (D) CH2  CH2  CH2
| | |
Cl Cl Cl

24. The major product of the following reaction is : (2017)

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

JEE Main (Archive) | DTS-2 107 Oxygen Containing Organic Compounds-I

25. Phenol on treatment with CO2 in the presence of NaOH followed by acidification produces compound X
as the major product. X on treatment with (CH 3CO)2 O in the presence of catalytic amount of H2 SO 4
produce : (2018)

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

26. 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 : (2018)

(A) (B)

(C) (D)

27. The major product formed in the following reaction is : (2018)

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

28. The major product of the following reaction is : (2018)

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

29. On treatment of the following compound with a strong acid, the most susceptible site for bond cleavage
is: (2018)

(A) C4  O5 (B) O2  C3 (C) O5  C6 (D) C1  O2

JEE Main (Archive) | DTS-2 108 Oxygen Containing Organic Compounds-I

30. The total number of optically active compounds formed in the following reaction is : (2018)

(A) four (B) two (C) six (D) zero

31. The products formed in the reaction of cumene with O2 followed by reactant with dil. HCl are : (2019)

(A) (B)

(C) (D)

32. The major product of the following reaction is : (2019)

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

33. The compounds A and B in the following reaction are, respectively : (2019)

(1) A = Benzyl chloride, B = Benzyl isocyanide (2) A = Benzyl chloride, B = Benzyl cyanide
(3) A = Benzyl alcohol, B = Benzyl isocyanide (4) A = Benzyl alcohol, B = Benzyl cyanide
34. The major product of following reaction is : (2019)
(1) AlH(i Bu)2
R  C  N 
?
(2) H2O

(A) RCOOH (B) RCONH 2 (C) RCHO (D) RCH2 NH 2

35. The major product of the following reaction is : (2019)

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

JEE Main (Archive) | DTS-2 109 Oxygen Containing Organic Compounds-I

36. Which is the most suitable reagent for the following transformation ? (2019)
OH
|
CH3  CH  CH  CH 2  CH  CH3  CH 3  CH  CH  CH 2CO 2H
(A) alkaline KMnO4 (B) CrO2Cl 2 / CS2
(C) I2 / NaOH (D) Tollen’s reagent

OH
|
37. CH3CH2  C  CH3 cannot be prepared by : (2019)
|
Ph
(A) HCHO  PhCH (CH3 )CH2MgX (B) CH3CH2COCH3  PhMgX
(C) PhCOCH2CH 3  CH3 MgX (D) PhCOCH 3  CH3CH 2MgX

38. The major product of the following reaction is : (2019)

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

39. What will be the major product when m-cresol is reacted with propargyl bromide (HC  C  CH 2 Br) in
presence of K 2CO3 in acetone? (2019)

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

40. The major product of the following reaction is: (2019)

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

JEE Main (Archive) | DTS-2 110 Oxygen Containing Organic Compounds-I

41. The major product of the following reaction is : (2019)

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

42. The major product of the following reaction is : (2019)

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

43. An organic compound neither reacts with neutral ferric chloride solution nor with Fehling solution. It
however, reacts with Grignard reagent and gives positive iodoform test. The compound is : (2019)

(A) (B)

(C) (D)

44. Arrange the following compounds in increasing order of C  OH bond length : (2020)
methanol, phenol, p-ethoxyphenol
(A) methanol < p-ethoxyphenol < phenol (B) phenol < p-ethoxyphenol < methanol
(C) phenol < methanol < p-ethoxyphenol (D) methanol < phenol < p-ethoxyphenol

45. 1-methyl ethylene oxide when treated with an excess of HBr produces: (2020)

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

JEE Main (Archive) | DTS-2 111 Oxygen Containing Organic Compounds-I

46. In the following reaction sequence, structures of A and B, respectively will be: (2020)

(A) (B)

(C) (D)

47. The major product [B] in the following sequence of reactions is: (2020)
( i) B2 H6 dil. H2 SO4
CH3  C  CH  CH2CH3  [A] 
 [B]
| (ii) H2O2 ,OHΘ 
CH(CH3 )2

CH3  C  CH  CH2CH3 CH2  C  CH2  CH2CH3

(A) | (B) |
CH(CH3 )2 CH(CH3 )2

CH3  C H  CH  CH  CH3
(C) | (D)
CH(CH3 )2

48. Among the compounds A and B with molecular formula C9H18O3 . A is having higher boiling point than

B. The possible structures of A and B are : (2020)

(A)

(B)

(C)

JEE Main (Archive) | DTS-2 112 Oxygen Containing Organic Compounds-I

 (D)

49. Consider the following reactions (2020)

(i) CH3MgBr Cu
A 

 B  2  methyl  2  butene
(ii) H3O 573 K

The mass percentage of carbon in A is ____________ .

50. The major product (Y) in the following reactions is: (2020)
CH3
|
HgSO ,H SO
4 2 4 2 5 2 (i) C H MgBr,H O
CH3  CH  C  CH  X Y
H2 O Conc.H2SO4 /

(A) (B)

(C) (D)

JEE Main (Archive) | DTS-2 113 Oxygen Containing Organic Compounds-I

 Date Planned : __ / __ / __ Daily Tutorial Sheet – 11 Expected Duration : 90 Min
Actual Date of Attempt : __ / __ / __ Numerical Value Type for Exact Duration :_________
JEE Main

126. How many of the following compounds undergoes oxidative cleavage on reaction with HIO4?

127. How many total number of aldehyde and carboxylic acid compounds are obtained when following
compounds undergo reaction with HIO4 ?

128. How many of the following compounds undergo pinacol-pinacolone rearrangement?

129.
How many — OH groups are present in product (A)

130.
How many atoms are present in one plane in product A?

131. How many –OH groups are present in (A)?

132.

If one mole of given compound reacts with HI then what is the value of x ?

DTS-11 | Numerical Value Type 101 Oxygen Containing Organic Compounds-I

133. How many of the following are more reactive than CH3CH(OH)CH3 for Lucas reagent?
 CH3CH2CH2OH

134. How many compounds give victor-Meyer test and produce red colouration.

135. How many of the following pairs of compounds can be distinguished by victor’s Meyer’s test?


CH3 CH3
| |
 CH3CH  I , CH3  CH  OH


CH3
|
 CH3NO2, CH3  CH  NO2

136. An unknown compound (A) having molar mass = 180, on acylation gives a product whose molar mass =
390, then find the number of hydroxyl groups present in compound A.

137.

One mole of given compound is reacted with HIO4 , how many moles of HIO4 are consumed ?

DTS-11 | Numerical Value Type 102 Oxygen Containing Organic Compounds-I

138. 0.092 g of a compound (A) with the molecular formula C3H8O3 on reaction with an excess of CH3MgI

gives 67 mL of methane at STP. The number of active hydrogen atoms present in a molecule of the
compound (A) is:
139. How many primary alcohol (including stereoisomers) are possible with formula C5H12O ?

140. If (  )2  methyl butanoic acid were esterified by reaction with (  )2  butonal, how many optically active
compounds would be present in the final equilibrium reaction mixture?

DTS-11 | Numerical Value Type 103 Oxygen Containing Organic Compounds-I