Date Planned : __ / __ / __ CBSE Pattern Expected Duration : 90 Min

Actual Date of Attempt : __ / __ / __ Level-0 Exact Duration :_________

Very Short Answer Type (1 Mark)
1. Arrange the following compounds in an increasing order of their acidic strength. Benzoic acid,
4-nitrobenzoic, 3, 4 dinitrobenzoic acid, 4-methoxy benzoic acid.
2. Arrange the following compounds in an increasing order of their acid strengths
(CH3 )2 CHCOOH, CH3CH2CH(Br)COOH, CH3CH(Br)CH2COOH
(A )
3. Identify A in the given reaction : RCOCl  H2 
 RCHO
4. What happens when methylbenzene is oxidized with alkaline KMnO4 ?
5. Given two uses of carboxylic acid.
6. How will you convert Benzaldehyde into – hydroxyl phenyl acetic acid?
Short Answer Type-I (2 Marks)
7. Write IUPAC names of the following compounds :
(i) CH3CH CH2COOH (ii) CH3CH2CH2COOC2H5
|
OH
8. Give chemical tests to distinguish between following pair of compounds.
(i) Benzoic acid and ethyl benzoate (ii) Methyl acetate and ethyl acetate
9. Illustrate the following reactions giving a chemical equation for each.
(i) Hell Volhard Zelinsky reaction (ii) Decarboxylation
10. How you will convert Bromobenzene to Benzoic acid?
11. State reasons for the following.
(i) Ethanoic acid is a weaker acid than benzoic acid.
(ii) Monochloro ehtanoic acid has a higher pK a value than dichloro ethanoic acid.

12. Account for the following

(i) Among CH3COCl and CH3CONH2 , CH3COCl is more susceptible to nucleophilic attack.
(ii) Benzoic acid does not undergo Friedal craft reaction.
13. Although phenoxide ion has more number of resonating structure than carboxylate ion, carboxylic acid is
a stronger acid than phenol. Why?
Short Answer Type-II (3 Marks)
14. How are the following conversions carried out?
(i) Benzoic acid to benzaldehyde (ii) Ethyl cyanide to Ethanoic acid
(iii) Benzoic acid from ethyl benzene
15. Give plausible explanation for each of the following :
(i) Cyclohexanone forms cyanohydrins in good yield but 2,2,6-trimethylcyclohexanone does not.
(ii) There are two  NH2 groups in semicarbazide. However, only one is involved in the formation of
semicarbazones.
(iii) During the preparation of esters from a carboxylic acid and an alcohol in the presence of an acid
catalyst, the water or the ester should be removed as soon as it is formed.

CBSE Pattern 198 Level - 0 | Oxygen Containing Organic Compounds-III

16. An organic compound contains 69.77% carbon, 11.63% hydrogen and rest oxygen. The molecular mass
of the compound is 86. It does not reduce Tollen’s reagent but forms an addition compound with sodium
hydrogensulphite and give positive iodoform test. On vigorous oxidation it gives ethanoic and propanoic
acid. Write the possible structure of the compound.
17. Identify A to E in the following sequence.
3 NH
2 Br / KOH HONO
2  D 
4 [O] Ca (OH) LiAlH
CH3CH2COOH  A 
 B  C 
 CH3COOH  E
 Dil. HCl

18. Complete the following equation giving the names of the reactants and the products.
 Anhyd. AlCl
3  C H COCH
(i) (CH 3COO )2 Ca  (ii) C6 H6  ....  6 5 3
LiAlH
4
(iii) (CH3 )2 CO 
19. What is -hydrogen in a carbonyl compound? Write similarities and differences on the reactivity of the
compound CH3CHO and C6 H5CHO with the reagents.
(i) NaOH (ii) Tollen’s reagent
Long Answer Type (5 Mark)

20. An organic compound (A) (molecular formula C8H16O2 ) was hydrolysed with dilute sulphuric acid to give
a carboxylic acid (B) and an alcohol (C). Oxidation of (C) with chromic acid produced (B). (C) on
dehydration gives but-1-ene. Write equations for the reactions involved.
21. An organic compound X undergoes acid hydrolysis to form two compounds Y and Z, Y reacts with
Na 2CO3 to form A. A is heated with soda lime to form B (CH4 ). Y on reduction with LiAlH4 forms Z.
Identify X, Y, Z, A, B and write the reactions involved.

22. An organic compound (A) on treatment with acetic acid in presence of conc. H2SO4 produces (B), (A) on
mild oxidation gives (C), (C) reacts with 50% KOH followed by acidification with dil HCl generates (A) and
(D), (D) reacts with PCl5 followed by reaction with ammonia gives (E), (E) on dehydration produces
hydrocyanic acid. Identify the compounds (A) to (E) and write chemical reactions involved.
23. An organic compound (A) on treatment with ethyl alcohol gives a carboxylic acid (B) and compound (C).
Hydrolysis of (C) under acidified conditions gives (B) and (D). Oxidation of (D) with KMnO4 also gives (B),
(B) on heating with Ca (OH)2 and dry distillation gives (E) having molecular formula C3H6O. (E) does not
give Tollen’s test and does not reduce Fehling solution but forms a 2, 4 dinitrophenyl hydrazone. Identify
A, B, C, D and E.
24. How will you prepare the following compounds from benzene? You may use any inorganic reagent and
any organic reagent having not more than one carbon atom.
(i) Methyl benzoate (ii) m-nitrobenzoic acid (iii) p-nitrobenzoic acid
(iv) Phenyl acetic acid (v) p-nitrobenzaldehyde

25. Some commercially important carboxylic acids are methanoic acid (formic acid), ethanoic acid (acetic
acid) and benzoic acid. These are used in various industries.
(i) How is methanoic acid manufactured?
(ii) Give important uses of methanoic acid?
(iii) How is methanol converted into ethanoic acid?
(iv) What are the important uses of ethanoic acid?
(v) Which salt of benzoic acid is used as food preservative?

CBSE Pattern 199 Level - 0 | Oxygen Containing Organic Compounds-III

 Date Planned : __ / __ / __ Daily Tutorial Sheet-1 Expected Duration : 90 Min
Actual Date of Attempt : __ / __ / __ Level-1 Exact Duration :_________

2 1. CO (O)
1. Identify C in the following reaction : CH  CH  CH 3MgBr  A 

 B  C
CH 4 2. H3O

(A) HOOC  CH2  COOH (B) OHC  CH2  COOH

(C)  COOH 2 (D) None of these

2. Which of the acids cannot be prepared by Grignard reagent?

(A) Acetic acid (B) Succinic acid (C) Formic acid (D) Benzoic acid

1.EtONa 1. OH  1. 
3. CH2 (COOEt)2 
 A 

 B 

C
2. EtBr 2. H3 O 2. H3 O

The compound (C) is :

(A) CH3CH2CH2CHO (B) CH3CH2CHO
(C) CH3CH2CH2COOH (D) CH3CH2COOH

4. Which of the following on oxidation can form carboxylic acid ?

I. CH 3CH 2OH II. (CH 3 )2 CHOH III. C 6 H5 CH2 OH

(A) Only III (B) Only I (C) Both I & III (D) None of these

5. Which of the following will not produce benzoic acid by oxidation with alkaline KMnO4 ?

CH3
|
(A) Ph  CH3 (B) Ph  CH2  Cl (C) Ph  CH2CH3 (D) Ph  C  CH3
|
CH3

6. A halogen compound A on hydrolysis with dilute alkali followed by acidification gives acetic acid.
The compound A is :
(A) ClCH 2 CH2 Cl (B) CH3 CHCl2
(C) ClCH2CHCl2 (D) CH3 CCl3

7. The compound (D) obtained through the following sequence of reactions is :

Alc. KOH Br
2  B  C 
3 KCN H O
C2 H5 Br 
 A  D

CCl 4 (Excess)

(A) Succinic acid (B) Malanic acid (C) Maleic acid (D) Oxalic acid

3 H O
diazomethane
8. P and Q in the given reaction sequence: R  C  N  P 
  Q , are given by the set :
HBF4

(A) Carboxamide, Carbonitrile (B) Carboxylic acid, Carbonitrile

(C) RCOOH, RCOOCH3 (D) RCONH2 , RCOCH3

9. The gas evolved on heating alkali formate with soda-lime is :

(A) CO (B) CO2 (C) hydrogen (D) water vapour

10. An organic compound is boiled with aqueous potash. The product is cooled and acidified with HCl.
A white solid separates out. The starting compound may be :
(A) ethyl benzoate (B) ethyl formate (C) ethyl acetate (D) methyl acetate

Level-1 | DTS-1 200 Oxygen Containing Organic Compounds-III

11. Consider the following sequence of reactions.

Identify A, B, C and D.
(A) F,  COOH,  COCH3 ,  OCH2CH2CH3 (B)  CHO,  COOH,  COCl,  COCH2 CH3
(C) Br, COOH,  COCl,  COCH2CH3 (D) Br, COOH,  COCl,  CHO

12. Cinnamic acid is formed when C6H5  CHO condenses with (CH3CO)2 O in presence of :
(A) concentrated H2SO4 (B) sodium acetate
(C) sodium metal (D) anhydrous ZnCl 2

*13. Formic acid can be prepared from which of the following reaction sequence ?
Glycerol High T H
(A) (COOH)2  (B) CO  NaOH 
 
283 K High P

KMnO
4  aq. KOH H
(C) CH3 OH 

(D) CHCl3 
 
H

14. When acetamide is hydrolysed by boiling with acid, the product obtained is :
(A) Acetic acid (B) Ethyl amine (C) Ethanol (D) Acetamide

*15. Which of the following are correct methods for the preparation of propanoic acid ?
HBr 2  Mg CO
(A) H3C  CH  CH2 
  
 Ether H3 O

3 BH  THF
4  KMnO
(B) H3C  C  CH 

 
H2 O2 , OH

HBr 2  Mg CO
(C) H2C  CH2 
  
 Ether H3 O

3  O
H3C  CH  C  CH3 
(D) | H2 O
CH3

Level-1 | DTS-1 201 Oxygen Containing Organic Compounds-III

 Date Planned : __ / __ / __ Daily Tutorial Sheet-2 Expected Duration : 90 Min
Actual Date of Attempt : __ / __ / __ Level-1 Exact Duration :_________

16. The reagent which does not give acid chloride on treating with a carboxylic acid is :
(A) PCl5 (B) Cl 2 (C) SOCl 2 (D) PCl3

17. When CH3COOH reacts with CH3  Mg X :

(A) CH3COX is formed (B) Methane is formed

(C) Acetone is formed (D) No reaction

18. Which of these does not contain  COOH group and yet the strongest of all ?
(A) Aspirin (B) Benzoic acid (C) Picric acid (D) Salicylic acid
19. 4-methyl benzene sulphonic acid reacts with sodium acetate to give.

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

1. Br2 / P 1. KCN
20. CH3COOH 
 Y 

 X . Here, X is :
2. H2 O 2. H3 O

(A) glycolic acid (B)  -hydroxy propionic acid

(C) succinic acid (D) malonic acid
21. In a set of the given reactions, acetic acid yielded a product C.

CH3COOH  PCl5  A

6 6 C H 2 5 1.C H MgBr
A   C . Product C would be :
B 
anhy. AlCl3 2.H2O

C2H5
(A) CH3CH(OH)C6H5 (B) | (C) CH3CH(OH)C2H5 (D) CH3COC6H5
CH3  C(OH)C6H5
22. The compound formed when sodium ethoxide reacts with ethanoyl chloride is :
(A) diethyl ether (B) 2-butanone (C) ethyl chloride (D) ethyl ethanoate
23. Acetic anhydride is best prepared in the laboratory by heating sodium acetate with :
(A) ethyl chloride (B) acetyl chloride (C) conc. H2SO4 (D) zinc dust

24. In the reaction :

The structure of the product T is :

(A) (B)

(C) (D)

Level-1 | DTS-2 202 Oxygen Containing Organic Compounds-III

25. Which one of the following will undergo meta-substitution on monochlorination?
(A) Ethoxybenzene (B) Chlorobenzene
(C) Ethyl benzoate (D) Phenol


2 5 2 P O H O/H
26. Identify Z in the sequence CH3COONH4 
 X   Y Z .


(A) CH3CH2CONH2 (B) CH3CN

(C) CH3COOH (D) (CH3CO)2 O

27. The most suitable reagent A, for the reaction is(are) :

(A) O3 (B) H2O2

(C) NaOH  H2O2 (D) m-chloroperoxybenzoic acid

28. When CH2  CH  COOH is reduced with LiAlH4 , the compound obtained will be :

(A) CH3  CH2  COOH (B) CH2  CH  CH2OH

(C) CH3CH2CH2OH (D) CH3CH2CHO

29. Which one of the following pairs gives effervescence of CO2 with aq. NaHCO3 ?

I. CH3COCl II. CH3COCH3 III. CH3COOCH3 IV. CH3COOCOCH3

The correct choice is :

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

30. Which of the following gives oxalic acid?

(A) Heating of acetic acid (B) Action of nitric acid on glucose
(C) Acidic hydrolysis of cyanogen, (CN)2 (D) Strong heating of sodium formate

Level-1 | DTS-2 203 Oxygen Containing Organic Compounds-III

 Date Planned : __ / __ / __ Daily Tutorial Sheet-3 Expected Duration : 90 Min
Actual Date of Attempt : __ / __ / __ Level-1 Exact Duration :_________

31. An ester (A) with molecular formula C9H10O2 was treated with excess of CH3MgBr and the complex so

formed was heated with H2SO4 to give an olefin (B). Ozonolysis of (B) gave a ketone with molecular

formula C8H8O which shows positive iodoform test. The structure of (A) is :

(A) C6H5COOC2H5 (B) C6H5COOC6H5

(C) C6H5COOCH3 (D) p  H3CO  C6H4  COCH3

32. Which of the following diacid readily gives anhydride on heating?

(A) Fumaric acid (B) Maleic acid (C) Malonic acid (D) Terephthalic acid
H2 O
33. (CH2CO)2 O  RMgX   Pr oduct ?  CH2CO
  2 O : Succinic anhydride
(A) ROOC(CH2 )COOR (B) RCOCH2CH2COOH

(C) RCOOR (D) RCOOH

34. Trans esterification is the process of :

(A) conversion of an aliphatic acid to ester
(B) conversion of an aliphatic alcohol to ester
(C) conversion of one ester to another ester
(D) conversion of an ester into its components namely acid and alcohol
35. Rate of reaction:

Is fastest when Z is _________ and slowest when Z is _______.

(A) Cl,OC2H5 (B) NH4 ,Cl (C) Cl,NH2 (D) Cl, O  COCH3

1. CH3  C  OC2H5

O Na CH3Br
36. CH3 MgX 
  A  B 
  C . The product C is :

2. H3O
(Excess)

O

(A) CH3  C  CH3 (B) (CH3 )3 C  O  CH3

(C) (CH3 )3 C  OH (D) (CH3 )2 C  CH2

2 2 Cl H O Alc. KOH
37. End product of the given reaction is : CH3CH2COOH   X 

red P

CH3CHCOOH CH2CH2COOH
(A) | (B) |
OH OH
CH2CHCOOH
(C) CH2  CHCOOH (D) | |
OH OH

Level-1 | DTS-3 204 Oxygen Containing Organic Compounds-III

38. A nitrogen containing organic compound gave an oily liquid on heating with bromine and potassium
hydroxide solution. On shaking the product with acetic anhydride, an antipyretic drug, (acetanilide) was
obtained. The reactions indicates that the starting compound is :
(A) aniline (B) benzamide (C) acetamide (D) nitrobenzene

H
39. CH3COOCH3  excess PhMgBr  product  X


The product X is :
(A) 1, 1-diphenylethanol (B) 1, 1-diphenylethene
(C) methyl phenylethanol (D) methyl phenylketone

40. Ethyl benzoate reacts with PCl5 to give :

(A) C2H5Cl + C6H5COCl + POCl3 + HCl (B) C2H5Cl + C6H5COCl + POCl3

(C) CH3COCl + C6H5COCl + POCl3 (D) C2H5Cl + C6H5COOH + POCl3

41.

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

42. The product of acid hydrolysis of P and Q can be distinguish by :

(A) Lucas reagent (B) 2, 4-DNP

(C) Fehling’s solution (D) FeCl 3

43. When an acyl chloride is reacted with phenol in presence of pyridine, the product is an :
(A) ester (B) anhydride (C) alkene (D) aldehyde

44. Acetamide and ethyl amine are distinguished by reacting with :

(A) Br2 water (B) acidic KMnO4
(C) aq. NaOH and heat (D) aq. HCl and heat

45. The refluxing of Me2N  COMe in acid gives :

(A) Me2NH  CH3COOH (B) Me2N  COOH  CH4
(C) MeOH  CH3CONH2 (D) CH3CH2NH2  CH3COOH

Level-1 | DTS-3 205 Oxygen Containing Organic Compounds-III

 Date Planned : __ / __ / __ Daily Tutorial Sheet-4 Expected Duration : 90 Min
Actual Date of Attempt : __ / __ / __ Level-1 Exact Duration :_________

46. Acid hydrolysis of an ester is reversible because:

(A) Alcohol and acid react together to form ester
(B) Protonation of ester makes carbonyl carbon more reactive for nucleophilic attack
(C) Proton being strong nucleophile, favours hydrolysis
+
(D) H3O is a nucleophile as well as electrophile

47. Alkaline hydrolysis of ester is irreversible because of :

(A) Carboxylate ion (a nucleophile) cannot attack alcohol (a nucleophile)
(B) Carboxylate is resonance stabilised
(C) Both (A) and (B)
(D) None the above

48. Select the INCORRECT statement.

(A) NaOH is strong enough to remove the proton from phenols and carboxylic acid
(B) NaHCO3 is strong enough to remove the proton of carboxylic acids
(C) Mixture of phenol and succinic acid can be separated using NaHCO3
(D) Mixture of phenol and succinic acid can be separated using NaOH

49. Fehling’s solution can make distinction between following pairs :

I. CH3COOH,HCOOH II. CH3COOH, HCHO

III. C6H5CHO, HCHO IV. CH3CHO, HCHO

Select the correct pairs :

(A) I, II, III (B) II, III, IV (C) II, III (D) II only

50. Which has maximum value of equilibrium constant ?

(A) 
CH3COOH  H2O  
 CH3COO  H3O


(B) 
HCOOH  H2O  
 HCOO  H3O


(C) 
C6H5COOH  H2O  
 C6 H5COO  H3O


(D) 
CF3COOH  H2O  
 CF3COO  H3O


51. When salicylic acid is nitrated:

(A) –COOH group is knocked out and product is picric acid
(B) –OH group is knocked out and products is m-nitrobenzoic acid
(C) –OH and –COOH groups both are knocked out and product is 1, 3, 5-trinitrobenzoic acid
(D) product is 2-hydroxy 5-nitrobenzoic acid

52. Which gives unsaturated acid on heating?

(A) CH3 C H CO2H (B) CH3  C H  CH2 COOH
| |
OH OH
(C) C H2 CH2CH2CO2H (D) All of these
|
OH

Level-1 | DTS-4 206 Oxygen Containing Organic Compounds-III

53. Which is more basic oxygen in an ester?

O
||
R  C  O  R


(A) O denoted by  (B) O denoted by 

(C) Both equally (D) None of the above oxygen atoms is basic

54. An optically active compound ‘X’ has molecular formula C4H8O3. It evolves CO2 with aq. NaHCO3.
‘X’ reacts with LiAlH4 to give an achiral compound. ‘X’ is :
CH3CH2 C HCOOH CH3 C HCOOH
(A) | (B) |
OH OMe
CH3 C HCOOH CH3 C HCH2COOH
(C) | (D) |
CH2OH OH
H
55. Identify the final product in the reaction CH3CHCOOH 
| Warm
OH

(A) (B) CH2  CHCO2H

O
||
(C) CH3 C CO2H (D) CH3CH2OH

56. Ease of esterification of the following acids with CH3OH is :

I. HCOOH II. CH 3 COOH III. CH 3 CH2 COOH

(A) III < II < I (B) I < II < III

(C) II < I < III (D) equal

57. Ease of esterification of the following alcohols with HCOOH is :

I. CH3CH2OH II. (CH3 )2 CHOH III. (CH3 )3 COH
(A) I < II < III (B) III < II < I
(C) II < I < III (D) equal
O
 1. NaBH4
58. End product of this conversion CH3 C CH2CH2CH2CO2 H  
 is :

2. H2 O H (Heat)

(A) (B)

CH3 C HCH2 CH2CH2CO 2H

(C) (D) |
OH

Level-1 | DTS-4 207 Oxygen Containing Organic Compounds-III

59. Which of the following compounds will undergo decarboxylation on heating?

(A) 2 and 3 (B) 3 and 4 (C) 3 only (D) 1 and 4

60. Which of the compounds yields a lactone after being reduced with sodium borohydride and heated with
a mineral acid ?

(A) (B)

(C) Both (A) and (B) (D) None of the above

Level-1 | DTS-4 208 Oxygen Containing Organic Compounds-III

 Date Planned : __ / __ / __ Daily Tutorial Sheet-5 Expected Duration : 90 Min
Actual Date of Attempt : __ / __ / __ Level-1 Exact Duration :_________

61. Consider the following statements.

I. In both the alcohol and carboxylic acid series, the smaller anion can be better solvated, leading
to a larger acidity of the corresponding conjugate acid.

II Acid strength of :

III Acid strength of :

Select the correct statements :

(A) I, II and III (B) I and II (C) II and III (D) I and III

62. In the following multi-step synthesis, products A, B and C are :

O O
|| ||
*  I2 /NaOH CaO/NaOH
CH3CH2 C CH2 C OH  A  B  C  D
 

O O O
|| || ||
(A) CH3CH2 C C H3, CH3CH2 C ONa, C HI3 (B) CH3CH2 C ONa,CHI3 ,CH3 C H3
* * *

O O
|| ||
(C) CH3CH2 C ONa, CHI3, CH3CH3 (D) CH3CH2 C ONa,CHI3 ,CH3CH3

2 3 1. Br / P NH
63. In the following reaction, RCH2 COOH  X 
  Y
2. H2 O alc.

The major amounts of X and Y are :

(A) RCHBrCONH2 ;RCH(NH2 )COOH (B) RCHBrCOOH;RCH(NH2 )COOH

(C) RCH2COBr ;RCH2COONH4 (D) RCHBrCOOH;RCH2CONH2

64. Which one of the following order of acid strength is correct ?

(A) RCOOH  HOH  CH  CH  ROH (B) RCOOH  CH  CH  HOH  ROH
(C) RCOOH  ROH  HOH  CH  CH (D) RCOOH  HOH  ROH  CH  CH

65. In the following sequence of reactions,

Select the correct statements about D.

(A) D has chiral centre (B) D is  -hydroxy acid
(C) Both of the A and B (D) None of the above

66. Consider the following reactions:

3 H O 3 NaOH/H O 3 H O
I. CH3NC  II. CHCl 3 
 III. CCl 4 
HCOOH is obtained in:
(A) I, II and III (B) II and III (C) I and II (D) I and III

Level-1 | DTS-5 209 Oxygen Containing Organic Compounds-III

67. CH  CH on reaction with CH3COOH in presence of Hg 2 gives X which is hydrolysed to Y. X and Y
are:
X Y
(A) CH3CH(OCOCH3 )2 CH3COCH3
(B) CH3CH(OCOCH3 )2 CH3CHO
(C) CH3CHO CH3CHO
(D) CH 3 CH(OCOCH3 )2 CH3CH2CHO

68. Carboxylic acid undergoes ionization due to :

(A) hydrogen bonding (B) absence of  -hydrogen
(C) high reactivity of  -hydrogen (D) resonance stabilization of carboxylate ion

69. B is:

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

*70. Which of the following statements is(are) TRUE about HCOOH ?

(A) It is a stronger acid than CH3COOH
(B) It forms formyl chloride with PCl5 at room temperature
(C) It gives CO and H 2 O on heating with conc. H2 SO 4
(D) It reduces Tollen's reagent
3 CH MgBr 2  B CO
71. H3C  C  CH 
 CH4  A  B will be :
H3 O

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

72. The reactivity of carboxylic acid derivatives towards nucleophilic acyl substitution is :
I. RCOCl II. (RCO)2 O III. RCOOR IV. RCONH2
(A) I > II > III > IV (B) I < II < III < IV (C) I < III < II < IV (D) IV < I < III < II

73. Diazotisation of aniline is done using NaNO2 and HCl at low temperature. Excess of HNO2 is destroyed by
the addition of :
(A) NaOH (B) NH4OH (C) NH2 – NH2 (D) NH2CONH2

*74. Select CORRECT statement(s).

(A) Urea is an amide of carbamic acid
(B) Urea is excreted in the urine as the end product of protein metabolism
(C) Urea is a diamide (D) CH3CN is named as methane nitrile

3 Al(OEt)
2 5 1. C H ONa
75. CH3CHO   A 

B A and B are respectively :
2. H

(A) CH3COOC2H5, CH3COCH2COOC2 H5 (B) CH3COOH, CH3COOC2 H5

(C) CH3COOH, CH3COCOOC2 H5 (D) CH3COOC2H5 , CH3COCH2COOH

Level-1 | DTS-5 210 Oxygen Containing Organic Compounds-III

 Date Planned : __ / __ / __ Daily Tutorial Sheet-6 Expected Duration : 90 Min
Actual Date of Attempt : __ / __ / __ Level-2 Exact Duration :_________

76. The acid catalysed dehydration to form ,  -unsaturated acid takes place in :
(A) lactic acid (B) glycolic acid
(C) 3-hydroxy propanoic acid (D) 4-Hydroxy butanoic acid
O

C6 H5CO3 H Tischenko
77. CH3  C  C2H5   A   B
Reaction
A and B are :
(A) CH3COOC2H5, CH3CHO (B) CH3COOC2H5, CH3CH2CHO
(C) CH3CH2COOCH3 , CH3CH2CHO (D) None is correct

78. A and B are :

(A) (B)

(C) (D) Formation of A and B is not possible

79. Which of the following can be reduced as well as oxidized ?

I. HCOOH II. CH 3 COOH III. CH 3 CH2 COOH
(A) Only I (B) Both I and II (C) I, II and III (D) None of these

80. Product (P) will be :

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

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

O O
  1. NaOCH2 CH3
CH3 CH2 C OCH3  H C OCH3 

 Product
2. H

O O O O
   
(A) CH3O C CH C OCH3 (B) H C OCH C OCH3
| |
CH3 CH3

O O O
  
(C) HOCH2CH C OCH3 (D) H C CH C OCH3
| |
CH3 CH3

Level-2 | DTS-6 211 Oxygen Containing Organic Compounds-III

82.

The compound B is :

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

83. Peroxyacetic acid (CH3CO3H) is a weaker acid than acetic acid (CH3CO2H) since :
O
||
(A) negative charge in CH3 COO can’t be delocalised into the carbonyl group
(B) CH3 group in CH3CO3H shows  I effect
(C) Both are correct
(D) None is correct

84.

The structure of product (X) :

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

85. Give the structure of the expected product of the following reaction.

(A) (B)

O

(C) CH3NH C CH2CH2 C HCH3 (D) None of these
|
OH

Level-2 | DTS-6 212 Oxygen Containing Organic Compounds-III

 Date Planned : __ / __ / __ Daily Tutorial Sheet-7 Expected Duration : 90 Min
Actual Date of Attempt : __ / __ / __ Level-2 Exact Duration :_________

86. D is :

(A) (B)

(C) (D)

87. Which of the following reactions is not reversible ?

H
(A) RCOOR   H2O  RCOOH  R  OH (B) RCOOR   NaOH  RCOONa  R  OH
2 H O/ H 
(C) RCOOH  R  OH  RCOOR   H2O (D) RCH  CH2  RCH(OH)CH3

*88. Which of the following will loose CO 2 on heating :
(A) methyl malonic acid (B) succinic acid
(C) 2, 2-dimethyl acetoacetic acid (D) Lactic acid

*89. The ester, RCOOR can be prepared by :

(A) esterification of RCOOH with R OH
(B) esterification of (RCO)2 O
(C) Baeyer-Villiger oxidation of RCOR with peroxybenzoic acid
(D) reaction of RCOCl with R OH

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

(A) At room temperature, formyl chloride is present in the form of CO and HCl
(B) Acetamide behaves as a weak base as well as a weak acid
4LiAlH
(C) CH 3CONH 2  C 2H5 NHCH3
3 H O
(D) CH3CONHR  CH3COOH  RNH2
91. Which of the following will undergo alkaline hydrolysis most rapidly ?

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

Paragraph for Questions 92 - 93

An organic compound X, C 4 H8O 3 evolves CO 2 on reaction with NaHCO 3 . It undergoes dehydration to give an
unsaturated compound Y which is highly stable. Y on oxidation with hot acidic KMnO4 gives P and Q.

92. X is :
(A) CH 3CH2CH(OH)COOH and is optically active
(B) CH3CH(OH)CH2COOH and is optically inactive
(C) CH3CH(OH)CH2COOH and is optically active
(D) HOCH2CH2CH2COOH and is optically inactive

Level-2 | DTS-7 213 Oxygen Containing Organic Compounds-III

93. P and Q are respectively:
(A) Both are (COOH)2 (B) Both are CH3COOH
(C) CH3COOH and (COOH)2 (D) CH3CHO and CHO  COOH

94. The barium salt of P on heating will give:

(A) (B)

(C) (D)

95. Consider the following sequence of reactions.

The products (B) and (C) are:

(A) PhCOOH and CH3 NH2 (B) CH3COOH and PhNH2
(C) PhCOCH3 and NH 2OH (D) PhCONHCH 3 and CH 3CONHPh

Level-2 | DTS-7 214 Oxygen Containing Organic Compounds-III

 Date Planned : __ / __ / __ Daily Tutorial Sheet-8 Expected Duration : 90 Min
Actual Date of Attempt : __ / __ / __ Level-2 Exact Duration :_________

2 5 C H ONa
96. The major product formed in the reaction C6H5CHO  CH3COOC2 H5  is :

C2 H5OH, heat

(A) C 6 H5CH(OH)CH 2COOC2 H5 (B) C 6 H5COCH 2COOC2 H5

(C) C 6 H5CH  CHCOOC2 H5 (D) C 6 H5COCOCH 3

97. The major product (Y) formed in the reaction sequence

1. EtONa 1. NaOH, heat
CH2 (CO2Et)2  X 

 Y is :

2. CH3 CHBrCO2 Et 2. H3 O
3. 150C

(A) CH3CHCOOH (B) CH3CH2 CHCOOH

| |
CH2COOH CH2COOH

(C) (CH 3 )2 CHCOOH (D)

Paragraph for Questions 98 - 100

An intra-molecular interaction is possible in a compound where both a carbanion (Nucleophile) and a carbonyl
group (electrophilic centre) is present. This is most favourable when it (cyclisation) leads to a product containing
a five or six membered ring.

98. A can be :

(A) (B)

(C) (D)

99. Identify the product in the following reaction ?

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

*100. Consider the reaction sequence :

O
|| Step 1 Step 2
BrMg(CH2 )5 MgBr  CH 3  C  OC2H5  (X ) 

Which of the following is(are) correct ?

(A) (X) in the above reaction contains a nucleophilic carbon and a carbonyl group
(B) Step 2 illustrate addition reaction
(C) (Y) can be oxidised to give a cycloalkanone
(D) (X) can react with H2O in a typical acid-base reaction

Level-2 | DTS-8 215 Oxygen Containing Organic Compounds-III

101. In which case cyclic amide is formed by heating?
CH2CH2 C HCOOH CH3CH C HCH2COOH
(A) | (B) |
NH2 NH2

C H2CH2CH2COOH
(C) | (D) All of these cases
NH2

 O O 
 || || 
Θ Θ
102. Acyl SN reaction is not possible R  C  X  Y  R  C  Y  X  when :

(A) X is NH2 and Y is Cl (B) X is OH and Y is NH2

(C) X is Cl and Y is OH (D) X is OR and Y is NH2

*
CH3 C HOH
103. | reacts with CH3COCl. Product formed :
C2 H5
(A) has retained configuration about chiral carbon (*)
(B) is racemic mixture
(C) loses chirality
(D) shows geometrical isomerism

104. Identify the end product of

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

O O
 
105. R C NH2 and R C OH can be best distinguished using :

(A) KOH / Br2 (B) SOCl 2

(C) NaNO2 & conc. HCl (D) Neutral FeCl 3 Solution

Level-2 | DTS-8 216 Oxygen Containing Organic Compounds-III

 Date Planned : __ / __ / __ Daily Tutorial Sheet-9 Expected Duration : 90 Min
Actual Date of Attempt : __ / __ / __ Level-2 Exact Duration :_________

O
 18
Conc.H2 SO4
106. H3C  C  OH  C2H5 OH   (X )
O
 18
Conc.H2SO 4

H3C  C  OH  CH3 3 C  OH   (Y)
In the above reaction (X) and (Y) are respectively:
O O CH
 18  | 3
(A) CH3  C  O  C2H5 and CH3  C  O  C  CH3
|
CH
3

O O CH
3
 18  18 |
(B) H3C  C  O  C2H5 and H3C  C  O  C  CH3
|
CH
3

O O CH
3
  |
(C) H3C  C  O  C2H5 and H3C  C  O  C CH3
|
CH
3

O O CH
3
  18 |
(D) CH3  C  O  C 2H5 and CH3  C  O  C  CH 3
|
CH
3

107.

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

108. Find the structure of compound R :

None of these
(A) (B) (C) (D)

Level-2 | DTS-9 217 Oxygen Containing Organic Compounds-III

109.

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

110.

O

(A) H2C  CH  CH2  CH2  C  OH (B)

(C) (D)

111.

(A) (B)

(C) H2 O, CO 2 and CO (D) HCOOH

112. In the given reaction :

3 2CH Br/NaNH
CH3CN  CH3CH2CN ,

intermediate is ________ and path is ______ :

(A) CH2CN, SN 1 (B) CH2CN, S N 2

(C) NH2 , SN 1 (D) CH3 , SN 2

*113. Select correct statement for the following base-catalysed hydrolysis :

O O
|| 18 Θ ||
OH
R  C  O  CH3   R  C  OΘ  CH3OH
(A) It is a nucleophilic acyl substitution (addition-elimination reaction)
18
(B) O appears in methanol CH3OH
(C) The reaction is not reversible
18
(D) O appears is carboxylate ion

Level-2 | DTS-9 218 Oxygen Containing Organic Compounds-III

*114. In Claisen condensation reaction :
(A) A proton is removed from the  -carbon to form a resonance-stabilized carbanion
(B) The carbanion acts as a nucleophile in a nucleophilic acyl substitution reaction with another
ester molecule
(C) A new C – C bond is formed
(D) The product formed has an active methylene group

4 LiAlH
115. Ester  CH3CH2OH (only)
(i) NaOC H
2 5
Ester 

A

(ii) H3 O

A is :
O O O O
|| || || ||
(A) CH 3 C CH 2 C OC2H5 (B) CH 3 C CH2 C OH
O
||
(C) CH3 C OH (D) None of the above

Level-2 | DTS-9 219 Oxygen Containing Organic Compounds-III

 Date Planned : __ / __ / __ Daily Tutorial Sheet-10 Expected Duration : 90 Min
Actual Date of Attempt : __ / __ / __ Level-2 Exact Duration :_________

116.

(A) C(CH3 )3 (B)

(C) (D)

117.

The product Q is :

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

118. Find the product (P) in given reaction setup.

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

119.

The product (X) is :

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

Level-2 | DTS-10 220 Oxygen Containing Organic Compounds-III

120.

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

121.

The major product formed in the reaction is :

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

122.

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

*123. Which of the following is(are) correct for following reaction sequence ?

5 1. PCl 2  E NaOH Br
A  C 
  D 
2. NH3 / Py Br2 ,  H2 O

(A) A is (B) C is (C) C is (D) E is

Level-2 | DTS-10 221 Oxygen Containing Organic Compounds-III

124. H  COOH and H  CHO can be distinguished by:
(A) Tollen’s reagent (B) Fehling’s solution
(C) NaHCO3 solution (D) NaOH / I2

*125. Which of the following compounds will liberate ammonia gas on refluxing with aqueous NaOH?

(A) C6H5CN (B)

O

(C) (D) Ph  C  NH  CH3

Level-2 | DTS-10 222 Oxygen Containing Organic Compounds-III

 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 give coloration with neutral FeCl 3 ?

127. How many of the following give CO2 with NaHCO3 ?

128. How many react with NaOH?

CH3COOH, CH3CHO, CH3COCH3 , CH3CH2OH, PhOH, PhCOOH, CH3CH2OCH3

129. How many carbon atoms are present in (A)?

130. How many ‘O’ atoms are present in (A)?

131. How many of the following give claisen rearrangement?

132. Percentage of oxygen in (P) is:

DTS-11 223 Oxygen Containing Organic Compounds-III

133. Number of alcoholic group in Q are:

134. How many nitro groups are present in (A) ?

135. How many ‘O’ atoms are present in (A) ?

O

CH3 OH
CH3 — C— OH   (A )
H

136. How many atoms of ‘O’ are present in B?

P O
2 5  (B)
CH3 — C— OH 
 
O

137. How many of the following give nucleophilic substitution reaction?

O CH3 — C— NH2
 
CH3COOH CH3 — C— Cl O
, , , , ,

138. How many of the following give NH3 gas on heating?

CH3CONH2, CH3CH2NH2, CH3CN

139. How many carboxylic acids are more acidic than C6 H5COOH ?

140. How many compounds do not give lactone on heating?

CH3CH2 CH— COOH
|
OH
CH3 CH— CH2COOH
|
OH
CH3 CH — CH2CH2 COOH
|
OH

DTS-11 224 Oxygen Containing Organic Compounds-III

 Date Planned : __ / __ / __ Daily Tutorial Sheet-1 Expected Duration : 90 Min
Actual Date of Attempt : __ / __ / __ JEE Main (Archive) Exact Duration :_________

1. A compound with molecular mass 180 is acylated with CH3COCl to get a compound with molecular
mass 390. The number of amino groups present per molecule of the former compound is : (2013)
(A) 2 (B) 5 (C) 4 (D) 6

2. An organic compound A upon reacting with NH3 gives B. On heating, B gives C. C in the presence of
KOH reacts with Br 2 to give CH3CH2NH2. A is : (2014)
(A) CH3COOH (B) CH3CH2CH2COOH
(C) CH  CH  COOH (D) CH3CH2COOH
|
CH3
3. In the presence of small amount of phosphorous, aliphatic carboxylic acids react with chlorine or
bromine to yield a compound in which  -hydrogen has been replaced by halogen. This reaction is
known as : (2015)
(A) Wolff - Kishner reaction (B) Etard reaction
(C) Hell - Volhard - Zelinsky reaction (D) Rosenmund reaction

4. Bouveault-Blanc reduction reaction involves : (2016)

(A) Reduction of an acyl halide with H2 / Pd
(B) Reduction of an ester with Na /C2H5OH
(C) Reduction of a carbonyl compound with Na/Hg and HCl
(D) Reduction of an anhydride with LiAlH4
5. The major product expected from the following reaction is: (2017)

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

6. The major product obtained in the following reaction is : (2017)

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

JEE Main (Archive) | DTS-1 225 Oxygen Containing Organic Compounds-III

7. The increasing order of the reactivity of the following with LiAlH4 is : (2019)

A. B. C. D.

(A) (A) < (B) < (D) < (C) (B) (B) < (A) < (C) < (D)
(C) (A) < (B) < (C) < (D) (D) (B) < (A) < (D) < (C)
8. The decreasing order of ease of alkaline hydrolysis for the following esters is : (2019)

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

9. An aromatic compound ‘A’ having molecular formula C7H6O2 on treating with aqueous ammonia and
heating forms compound ‘B’ the compound ‘B’ on reaction with molecular bromine and potassium
hydroxide provides compound ‘C’ having molecular formula C6H7N. The structure of ‘A’ is : (2019)

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

10. Which dicarboxylic acid in presence of a dehydrating agent is least reactive of given an anhydride ?

(A) (B) (C) (D) (2019)

11. The major product obtained in the following reaction is : (2019)

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

JEE Main (Archive) | DTS-1 226 Oxygen Containing Organic Compounds-III

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

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

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

LiAIH4
CH3CH  CHCO2CH3 


(A) CH3CH2CH2CHO (B) CH3CH2CH2CO2CH3

(C) CH3CH2CH2CH2OH (D) CH3CH  CHCH2OH

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

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

15. Identify (A) in the following reaction sequence : (2020)

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

16. What is the product of the following reaction? (2020)

(i) NaBH 4
Hex  3  ynal 

(ii) PBr3
(iii ) Mg/ether
(iv ) CO2 /H3 O

(A) (B)

(C) (D)

JEE Main (Archive) | DTS-1 227 Oxygen Containing Organic Compounds-III

17. The most suitable reagent for the given conversion is : (2020)

(A) B2H6 (B) LiAlH4 (C) H2 / Pd (D) NaBH4

18. Consider the following molecules and statements related to them : (2020)

(A) (B)

(a) (B) is more likely to be crystalline than (A)

(b) (B) has higher boiling point than (A)
(c) (B) dissolves more readily than (A) in water
Identify the correct option from below:
(A) (a) and (c) are true (B) only (a) is true
(C) (b) and (c) are true (D) (a) and (b) are true
19. An organic compound [A], molecular formula C10H20O2 was hydrolyzed with dilute sulphuric acid to give

a carboxylic acid [B] and an alcohol [C]. Oxidation of [C] with CrO3  H2SO4 produced [B]. Which of the

following structures are not possible for [A] ? (2020)

CH3
|
(A) CH3  CH2  CH  OCOCH2 CH  CH2CH3 (B) (CH3 )3  C  COOCH2C(CH3 )3
|
CH3

CH3
|
(C) CH3  CH2  CH  COOCH2  CH  CH2 CH3 (d) CH3CH2CH2COOCH2CH2CH2CH3
|
CH3

20. [P] on treatment with Br2 / FeBr3 in CCl 4 produced a single isomers C8H7O2Br while heating [P] with

sodalime gave toluene. The compound [P] is: (2020)

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

21. An organic compound (A) (molecular formula C6H12O2 ) was hydrolysed with dil. H2SO4 to give a

carboxylic acid (B) and an alcohol (C). `C gives white turbidity immediately when treated with anhydrous
ZnCl 2 and conc. HCl. The organic compound (A) is : (2020)

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

JEE Main (Archive) | DTS-1 228 Oxygen Containing Organic Compounds-III

 Date Planned : __ / __ / __ Daily Tutorial Sheet-1 Expected Duration : 90 Min
Actual Date of Attempt : __ / __ / __ JEE Advanced (Archive) Exact Duration :_________

1. Write the structural formula of main organic product formed when ethyl acetate is treated with double
the molar quantity of methyl magnesium bromide and the reaction mixture is poured into water. (1981)
2. Write the chemical equation to show what happens when, “Ethyl acetate is treated with sodium ethoxide
in ethanol and the reaction mixture is acidified.” (1981)
3. An alkene A on ozonolysis yields acetone and an aldehyde. The aldehyde is easily oxidised to an acid B.
When B is treated with bromine in presence of phosphorus yields a compound C which on hydrolysis
gives a hydroxy acid D. This acid can also be obtained from acetone by the reaction with hydrogen
cyanide followed by hydrolysis. Identify the compounds A, B, C and D. (1982)
4. State with balanced equation, what happens when “Acetic anhydride reacts with phenol in presence of a
base.” (1982)
5. Acetamide is treated separately with the following reagents. Which one of these would give methyl amine?
(A) PCl5 (B) NaOH  Br 2 (1983)

(C) HOCH2CH2OH (D) Hot conc. H2SO4

6. Hydrolysis of an ester in the presence of a dilute acid is known as saponification. (1983)

7. Formic acid when heated with conc. H2SO4 produces ______________. (1983)

8. Give reasons for the following in one or two sentences. (1983)

“Acetic acid can be halogenated in the presence of P and Cl2 , but formic acid cannot be halogenated in
the same way”. Why?
9. Write down the reactions involved in the preparation of the following using the reagents indicated against
in parenthesis. Propionic anhydride from propionaldehyde [AgNO3, NH4OH, P2O5 ] (1984)

10. Give reasons in one or two sentences for the following : “Formic acid is a stronger acid than acetic
acid.” (1985)
11. A liquid X, having a molecular formula C6H12O2 is hydrolyzed with water in the presence of an acid to
give a carboxylic acid Y and an alcohol Z. Oxidation of Z with chromic acid gives Y. What are the
structures of X, Y and Z ? (1986)
12. Complete the following with appropriate structures : (1986)
C 2H5OH
(CH3CO)2 O  CH3COOH  ?

13. Arrange the following in order of their increasing ease of hydrolysis : (1986)
CH3COOC2H5 , CH3COCl, (CH3CO)2 O, CH3CONH2

14. Write balanced equations for the following reaction : (1987)

“Acetamide is reacted with bromine in the presence of potassium hydroxide.”
15. Give reason for : (1988)
“Carbon-oxygen bond lengths in formic acid are 1.23Å and 1.36Å and both the carbon-oxygen bonds in
sodium formate have the same value, i.e. 1.27Å”

JEE Adv (Archive) | DTS-1 229 Oxygen Containing Organic Compounds-III

 Date Planned : __ / __ / __ Daily Tutorial Sheet-2 Expected Duration : 90 Min
Actual Date of Attempt : __ / __ / __ JEE Advanced (Archive) Exact Duration :_________

16. The sodium salt of a carboxylic acid, A was produced by passing a gas, B into an aqueous solution of
caustic alkali at an elevated temperature and pressure. A, on heating in presence of sodium hydroxide
followed by treatment with sulphuric acid gave a dibasic acid, C. A. sample of 0.4 g of acid C, on
combustion gave 0.08g of water and 0.39 g of carbon dioxide. The silver salt of the acid C weighting 1.0 g
on ignition yielded 0.71 g of silver as residue. Identify A, B and C. (1990)
17. How will you bring about the following conversion? (1990)
“Ethanoic acid to a mixture of methanoic acid and diphenyl ketone.”
18. The boiling point of propanoic acid is less than that of n-butyl alcohol, an alcohol of comparable
molecular weight. (F/T) (1991)
19. Arrange the following as stated : (1991)
“Increasing order of acidic strength.”
ClCH2COOH, CH3CH2COOH, ClCH2CH2COOH, (CH3 )2 CHCOOH, CH3 COOH

20. In the following identify the compounds/reaction conditions represented by the alphabets A, B, and C :
5 PCl 3 2 5NH 2 P O H /Ni
C 6 H5COOH  A  B   C6H5CN  C (1991)
21. When propionic acid is treated with aqueous sodium bicarbonate, CO2 is liberated. The C of CO2 comes

from : (1992)
(A) methyl group (B) carboxylic acid group
(C) methylene group (D) bicarbonate group
22. Complete the following sequence of the reactions with appropriate structures : (1992)

(i)

(ii)

23. Complete the following reaction with appropriate structure. (1995)

NaOC2H5 in absolute C2 H5 OH
C6H5CHO  CH3COOC2H5 

heat

24. Complete the following sequence of reactions with appropriate structures. (1995)
Re d  P (i) Alc. KOH (excess)
CH 3  CH2  COOH 
 A 

B
Br2 ( ii) H

25. Which of the following carboxylic acids undergoes decarboxylation easily? Explain briefly. (1995)
(i) C6H5COCH2COOH (ii) C6H5COCOOH

(iii) C6H5CH(OH)COOH (iv) C6H5CH(NH2 )COOH

26. A hydrocarbon A of the formula C8H10, on ozonolysis gives compound B(C4H6O2 ) only. The compound
B can also be obtained from the alkyl bromide C (C3H5Br) upon treatment with magnesium in dry ether
followed by reaction with carbondioxide and acidification. Identify A, B and C and also give equations for
the reactions. (1996)

JEE Adv (Archive) |DTS-2 230 Oxygen Containing Organic Compounds-III

27. Complete the following, giving the structures of the principal organic products. (1997)

(i)

2conc. H SO
4
(ii) (COOH)2  (CH2OH)2    B

3 H O
(iii) H3CCOCOC6 H5  NaOH C

28. Statement-I : Acetic acid does not undergo haloform reaction. (1998)
Statement-II : Acetic acid has no alpha hydrogen.
(A) Statement-I is True, Statement-II is True and Statement-II is a correct explanation for
Statement-I
(B) Statement-I is True, Statement-II is True and Statement-II is NOT a correct explanation for
Statement-I
(C) Statement-I is True, Statement-II is False
(D) Statement-I is False, Statement-II is True

29. Identify all the products formed in the following reaction sequence and explain briefly the formation of
the products. (1999)

30. Write the structures of the products A and B. (2000)

O
|| 18
H3 O 
CH 3  C  O C2H 5  A B

JEE Adv (Archive) |DTS-2 231 Oxygen Containing Organic Compounds-III

 Date Planned : __ / __ / __ Daily Tutorial Sheet-3 Expected Duration : 90 Min
Actual Date of Attempt : __ / __ / __ JEE Advanced (Archive) Exact Duration :_________

31. Benzoyl chloride is prepared from benzoic acid by : (2000)

(A) Cl 2, hv (B) SO2Cl 2

(C) SOCl 2 (D) Cl2 , H2O

32. Identify X and Y in the following synthetic scheme and write their structures. Explain the formation of
*
labeled formaldehyde (H2 CO) as one of the products when compound (Z) is treated with HBr and
subsequently ozonolysed. Mark the C* carbon in the entire scheme. (2001)
*
Ba C O3  H2SO4  X

(C *  C14 )
(i) Mg/ether
4 LiAlH
CH2  CH  Br 
 Y 
(ii) X
(iii) H3O 

33. (±) 2-phenylpropanoic acid on treatment with (+)-2-butanol gives (A) and (B). Deduce their structures and
also establish stereochemical relation between them. (2003)
34. An enantiomerically pure acid is treated with racemic mixture of an alcohol having one chiral carbon. The
ester formed will be : (2003)
(A) Optically active mixture (B) pure enantiomer
(C) meso compound (D) racemic mixture
35. Benzamide on treatment with POCl 3 gives : (2004)

(A) aniline (B) benzonitrile

(C) chlorobenzene (D) benzyl amine

36.
(2004)

Identify A to D.
37. Which of the following reactants on reaction with conc. NaOH followed by acidification gives the following
lactone as the only product? (2006)

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

JEE Adv (Archive) | DTS-3 232 Oxygen Containing Organic Compounds-III

Paragraph for Questions 38-40 (2006)
RCONH2 is converted into RNH2 by means of Hofmann’s bromamide degradation.

NaOH

In this reaction, PhCONHBr is formed from which this reaction has derived its name. Electron donating group at
phenyl activates the reaction. Hofmann’s degradation reaction is an intramolecular reaction.
38. How can the conversion of (i) to (ii) be brought about ?
(A) KBr (B) KBr  CH3ONa

(C) KBr + KOH (D) Br 2  KOH

39. Which is the rate determining step in Hofmann’s bromamide degradation?

(A) Formation of (i) (B) Formation of (ii)
(C) Formation of (iii) (D) Formation of (iv)
40. What are the constituent amines formed when the mixture of (1) and (2) undergoes Hofmann’s
bromamide degradation?

(A)

(B)
(C)

(D)

41. Statement-I : p-hydroxybenzoic acid has a lower boiling point than o-hydroxybenzoic acid. (2007)
Statement-II : o-hydroxybenzoic acid has intramolecular hydrogen bonding.
(A) Statement-I is True, Statement-II is True and Statement-II is a correct explanation for
Statement-I
(B) Statement-I is True, Statement-II is True and Statement-II is NOT a correct explanation for
Statement-I
(C) Statement-I is True, Statement-II is False
(D) Statement-I is False, Statement-II is True

JEE Advanced (Archive) | DTS-3 233 Oxygen Containing Organic Compounds-III

42. Among the following compounds, the most acidic is (2011)
(A) p-nitrophenol (B) p-hydroxybenzoic acid
(C) o-hydroxybenzoic acid (D) p-toluic acid
43. Amongst the following, that total number of compounds soluble in aqueous NaOH is (2011)

44. In the reaction T the structure of the (2011)

Product T is

(A) (B)

(C) (D)

45. The carboxyl functional group (  COOH) is present in : (2012)

(A) picric acid (B) barbituric acid (C) ascorbic acid (D) aspirin

JEE Adv (Archive) | DTS-3 234 Oxygen Containing Organic Compounds-III

 Date Planned : __ / __ / __ Daily Tutorial Sheet-4 Expected Duration : 90 Min
Actual Date of Attempt : __ / __ / __ JEE Advanced (Archive) Exact Duration :_________

*46. Identify the binary mixture(s) that can be separated into individual compounds, by differential extraction,
as shown in the given scheme. (2012)

(A) C6H5OH and C6H5COOH (B) C6H5COOHand C6H5CH2OH

(C) C6H5CH2OH and C6H5OH (D) C6H5CH2OH and C6H5CH2COOH

47. The compound that undergoes decarboxylation most readily under mild condition is : (2012)

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

48. The compound that does NOT liberate CO2, on treatment with aqueous sodium bicarbonate solution, is
(A) Benzoic acid (B) Benzenesulphonic acid (2013)
(C) Salicylic acid (D) Carbolic acid (Phenol)
49. The total number of carboxylic acid groups in the product P. (2013)

Paragraph for Questions 50 - 51

P and Q are isomeric dicarboxylic acid C4H4O4. Both decolorize Br2/H2O. On heating, P forms a cyclic anhydride.
Upon treatment with dilute alkaline KMnO4. P as well as Q could produce one or more than one from compounds
S, T and U given : (2013)

Choose the correct option for 1 and 2 :

50. Compounds formed from P and Q are, respectively :

(A) Optically active S and optically active pair (T, U)
(B) Optically inactive S and optically inactive pair (T, U)
(C) Optically active pair (T, U) and optically active S
(D) Optically inactive pair (T, U) and optically inactive S

JEE Advanced (Archive) | DTS-4 235 Oxygen Containing Organic Compounds-III

51. In the following reaction sequence V and W are, respectively :

(A) (B)

(C) (D)
52. Different possible thermal decomposition pathways for peroxyesters are shown below. Match each
pathway from Column I with an appropriate structure from Column II and select the correct answer
using the code given below the lists. (2014)

Column I Column II

P. Pathway P 1.

Q. Pathway Q 2.

R. Pathway R 3.

S. Pathways S 4.

Codes
P Q R S P Q R S
(A) 1 3 4 2 (B) 2 4 3 1
(C) 4 1 2 3 (D) 3 2 1 4

JEE Advanced (Archive) | DTS-4 236 Oxygen Containing Organic Compounds-III

53. The correct order of acidity for the following compounds is : (2016)

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

54. Reagent(s) which can be used to bring about the following transformation is(are) (2016)

(A) LiAlH4 ,in (C2H5 )2 O (B) BH3 in THF

(C) NaBH4 in C2H5OH (D) Raney Ni / H2 in THF

Paragraph for Questions 55-56 (2018)

An organic acid P(C11H12O2 ) can easily be oxidized to a dibasic acid which reacts with ethylene glycol to produce
a polymer dacron. Upon ozonolysis, P gives an aliphatic ketone as one of the products. P undergoes the following
reaction sequences to furnish R via Q. The compound P also undergoes another set of reactions to produce S.
1) H2 /Pd  C
2) NH3 / 1) H2 /Pd  C 1) HCl
3) Br2 /NaOH
2 22) SOCl 2) Mg/Et O
S 
 P  Q R
4)CHCl 3 ,KOH, 3) MeMgBr,CdCl2 3)CO2 (dry ice)
5) H2 /Pd  C 4) NaBH4 4) H3O 

55. The compound R is

(A) (B)

(C) (D)

56. The compound S is

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

JEE Advanced (Archive) | DTS-4 237 Oxygen Containing Organic Compounds-III

57. The correct order of acid strength of the following carboxylic acids is : (2019)

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

JEE Advanced (Archive) | DTS-4 238 Oxygen Containing Organic Compounds-III