MKA Sir Unacademy Plus

Exercise - 01
1. Which of the following reaction is called as ‘Bouveault–Blanc reduction’
(1) Reduction of acyl halide with H2/Pd-BaSO4 (2) Reduction of ester with Na/C2H5OH
(3) Reduction of anhydride with LiAlH4 (4) Reduction of carbonyl compounds with Na-Hg/HCl
2. Glycol on treatment with PI3 mainly gives–
(1) Ethylene (2) Ethylene iodide (3) Ethyl iodide (4) Ethane
3 Consider the reaction of HI with the following:

II

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

(1) I and II both (2) II only (3) I only (4) none
4. Ethanol on reaction with Acetic anhydride gives
(1) Acetic ester (2) Formic ester
(3) Ethanoic acid (4) Acetic ester and Ethanoic acid both
5. Rate of hydration of

, ,

will be in order:
(1) I < II < III (2) I < III < II (3) II < I < III (4) III < II < I
6. The reaction of CH3OC2H5 with HI gives
(1) CH3I (2) C2H5OH (3) CH3I + C2H5OH (4) C2H5I + CH3OH
7. The number of methoxy groups in a compound can be determined by treating it with
(1) HI and AgNO3 (2) Sodium carbonate (3) Sodium hydroxide (4) Acetic acid
8. Most acidic alcohol out of following compounds is
(1) (CH3)3C–OH (2) CH3CH2OH (3) CH3OH (4) PhOH
9. Action of HNO2 on CH3NH2 gives following as major product
(1) CH3OH (2) CH3–O–CH3 (3) CH3–O–N=O (4) CH3–NO2
10. A compound ‘X’ with molecular formula C3H8O can be oxidised to a compound ‘Y’ with the molecular formula C 3H6O2, ‘X’
is most likely to be
(1) Primary alcohol (2) Secondary alcohol (3) Aldehyde (4) Ketone
11. Ether on carbonylation gives
(1) Alkanoic acid (2) Alkanone (3) Alkyl alkanoate (4) Alkanal
12. Phenol with Hinsberg’s reagent gives
(1) Sulphone (2) Sulphanilic acid (3) Sulphonic ester (4) Sulphonal

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13. Select the odd structure out
(1) CH3–CH(OH)–CH2–CH3 (2) CH3–CH(OH)–CH2–CH2–CH3
(3) CH3–CH(OH)–CH3 (4) CH3–CH2–CH(OH)–C2H5
KHSO LiAlH
14. Glycerol  
4  A  
4  B
A and B are:
(1) Acrolein, Allyl alcohol (2) Glyceryl sulphate, Acrylic acid
(3) Allyl alcohol, Acrolein (4) Only acrolein (B is not formed)

NaBH H / Pt
15. B  
4 CH = CH – CHO 2
 A, A and B are:

(1) CH2CH2CHO, CH = CH–CH2OH

(2) CH2CH2CH2OH, CH = CH – CH2OH

(3) CH= CH–CH2OH in both cases

(4) CH2CH2CH2OH in both cases

16.

Select schemes A, B, C out of

I acid catalysed hydration II HBO III oxymercuration-demercuration
(1) I in all cases (2) I, II, III (3) II, III, I (4) III, I, II
17. Dehydration of the alcohols

will be in order
(1) IV > III > II > I (2) I > II > III > IV
(3) IV > II > III > I (4) II > IV > I > III

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
18. H ? Product is:

(1) (2) (3) (4)

19. RMgX
  ? Product Obtained is:
H 2O

R R' R R
| | | |
(1) R 'C  CH 2 OH (2) RCH 2  C  OH (3) R ' CH  C  OH (4) R ' ' CH 2  C  OH
2
| | | |
R'' R'' R'' R'

I / NaOH
20. 
2
  
 H  A, A is

(1) (2) (3) (4)

CH OH
21. [A]
CH OH
 
3
 3
 [B] A & B are:
H 2SO 4
CH3O 

(1) & (2) &

(3) & (4) &

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22. . In this diol

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

(2) OH at C2 is more acidic than at C5.
(3) both have same basicity
(4) both have same acidic strength
23. 2,2,6,6-Tetramethyl cyclohexanol is treated with an acid. An alkene is formed after rearrangement. The structure of the
alkene is

(1) (2) (3) (4)

24. The product of the following reaction is

i) BH3 /THF
H3 C CH 2 ii) H2 O2 , OH
(1) 1-Pentanol (2) 2-Pentanol (3) Pentane (4) 1, 2-Pentanediol
O

Cl NaBH4
25. (A) Product(s) is/are –

LiAlH4

(B)

(1) [A] is an Alcohol ; [B] is an Aldehyde (2) [A] is an Aldehyde; [B] is an Alcohol
(3) [A] and [B] both are Alcohols (4) [A] and [B] both are Aldehydes
O

HCN LiAlH NaNO  HCl

26. (P) (Q) 
4  (R) 
2 
 (S)

Relationship between (P) and (S)

(1) Identical compound (2) Homologous compound (3) Position isomers (4) Chain isomers
27. Arrange the following in terms of solubility in water –
(1) C2H5OH < C6H5CH2OH < C6H5OH (2) C6H5CH2OH < C6H5OH < C2H5OH
(3) C6H5CH2OH < C2H5OH < C6H5OH (4) C6H5OH < C6H5CH2OH < C2H5OH

HBr
28. Ph  CH  CH 2 OH   Product. The product in the reaction is –
|
Ph
Br
/
(1) Ph  CH  CH 2 Br (2) Ph  C  CH 2 (3) Ph  C  CH 3 (4) Ph  C  CH 2  Ph
| | | |
Ph Ph Ph Br

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Passage (Q.29-Q.31)
R – NH2 reacts with HNO2 (NaNO2 + dil HCl) forming alcohols. Chemist A wanted to prepare 2-Propanol and thus he
worked out the synthesis from 2-Amino propane. Chemist B also wanted to prepare 2-Propanol but he could not arrange
2-Aminopropane but instead he tried the synthesis from 1-Aminopropane.
29. What was the major product of chemist B ?
(1) 1-Propanol (2) 2-Propanol (3) Propene (4) Cyclopropane
30. What are the most stable intermediate of Chemist A and B ?
A B A B
Å Å Å Å
(1) CH 3CH 2 CH 2 CH 3CH 2 CH 2 (2) CH 3 - CH - CH 3 CH 3 - CH 2 - CH 2

Å Å
(3) CH 3 - CHCH 3 CH 3 - CH - CH 3 (4) None of these

OH
HNO2
31. major product, is –
CH2NH2

OH OH
(1) (2) (3) O (4) OH
CH2OH CH3
Passage (Q.32-Q.34)
Compound [A] (C8H8O) is obtained from styrene on treatment with CF3CO3H. [A] can also be obtained from C8H8ClO on
treatment with concentrated NaOH. [A] on treatment with HBr produces an optically active compound [B]. Styrene on
treatment with HBr, H2O2 and then treatment with Mg/ether produces [C]. Compound [C] on treatment with RCOR'
produces an alkene [D] and RCH(OH)R'. Sytrene is PhCH = CH 2.
32. Structure of compounds [A] is –
(1) Ph – CH – CH2 (2) Ph - CH - CH 2 OH (3) PhCH2CH2MgBr (4) PhCH = CH2
|
O Br
33. Structure of compounds [B] is –
(1) Ph – CH – CH2 (2) Ph - CH - CH 2 OH (3) PhCH2CH2MgBr (4) PhCH = CH2
|
O Br
34. Structure of compounds [C] is –
(1) Ph – CH – CH2 (2) Ph - CH - CH 2 OH (3) PhCH2CH2MgBr (4) PhCH = CH2
|
O Br
35. What is a likely product of the reaction shown?

(1) (2) (3) (4)

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36. Compare rate of dehydration of a, b, c by conc. H 2SO4

(a) (b) (c)

(1) a > c > b (2) a > b > c (3) b > a > c (4) b > c > a

37. Major-product A is

(1) (2) (3) (4)

38. The major product of the following reaction sequence is:

(1) (2) (3) (4)

39. ; Reagent A may be:

(1) H2O/H+ (2) BH3.THF/H2O2–OH–

(3) Hg(OCOCH3)2.THF/NaBH4.NaOH (4) All are possible
40. Which of the following alcohols cannot be prepared from hydration of an alkene?

(1) (2) (3) (4)

41. Hydroboration of 1 - methylcyclopentene using B2D6 , followed by treatement with alkaline hydrogen peroxide, gives -

(1) (2) (3) (4)

CH3
| H HBr
KMnO 4
42. CH3  CH   ( A )  
(B)  (C)
|  ROOR

CH3

Product (C) in the above reaction is -

H CH3 CH3
| | |
(1) CH3  C  Br (2) CH3  C  Br (3) CH3  CH2 (4) CH3  CH
| | | |
CH3 CH3 CH2  Br CH2  Br

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43.

Product (B) of the above reaction is-

(1) (2) (3) (4)

44. Predict the major product.

(1) (2) (3) (4)

45. A is:

(1) (2) (3) (4)

46. Product (A) is:

(1) (2)

(3) (4)

1.Hg( OAc ) ,H O
47.   2 2
 Product; Product is -
2.NaBH 4

(1) (2) (3) (4)

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48. (1) (2)

(3) (4)

Sum of molecular mass of A, B, C, D, (i.e. A + B + C + D) is equal to :

49. Which of the following is the best set of reagents to perform the about conversion?

(1) ThO2,  (2) H3PO4,  (3) CH3COOH,  (4) Al2O3, 

50. Product– The main product is–

(1) (2) (3) (4)

51. An organic compound A (Molecular formula C6H12O) does not change the colour of acidic dichromate solution. Compound
A on treatment with H2SO4 produces alkene, which on oxidative ozonolysis gives a molecule (C6H10O3) which gives positive
iodoform test. Find out structure of 'A'.

(1) (2) (3) (4)

52. In the gives reaction, The product B is–

(1) Identical to A (2) Chain isomer of A (3) A positional isomer of 'A' (4) Reduced product of A

53.

(1) (2) (3) (4)

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54. The order of reactivity of following alcohols toward HCl is–

(1) 1 > 2 > 3 > 4 (2) 1 > 3 > 2 > 4 (3) 4 > 3 > 2 > 1 (4) 4 > 3 > 1 > 2
55. Which of the following reactions proceeds with retention of configuration–

(1) (2)

(3) (4)

56. X will be–

(1) (2)

(3) (4)

57. An organic compound having molecular formula C3H6O does not react with 2, –4dinitrophenyl hydrazine and does not react
with Na metal. The compound is expected to be–
(1) CH3CH2CHO (2) CH3COCH3 (3) CH2=CH–CH2–OH (4) CH2=CH–O–CH3

58. is prepared best by the reaction–

(1) (CH3)3C–Br + (CH3)3COK 

H SO
2 4
(2) (CH3)3C–OH  
140C
Al O
2 3
(3) (CH3)3C–OH  
240C
Conc. H2 SO 4 (CH3 )3 COH
(4) (CH3)2C=CH2      

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59. The major product formed in the reaction is–

(1) (2) (3) (4)

60. Which of the following ethers is the most unreactive to cleavage with conc. HBr ?

(1) Ph—CH2—O—CH3 (2) Ph—O—Ph (3) (4)

61. Reagent A used in this change is–

(1) B2H6 (2) LiAlH4 (3) Sn/HCl (4) NaBH4

62.

(1) (2) (3) (4)

63. Find out (X):

(1) (2) (3) (4)

64. Product–

(1) (2) (3) (4)

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65. (major)–

(1) (2) (3) (4)

66.

The labelled –O18 will be in–

(1) H2O (2) Methyl benzoate (3) Both 1 and 2 (4) Benzoic acid

67. (P); Product (P) is–

(1) (2) (3) (4)

68.

Above conversion can be done by–

(1) NaBH4 (2) LiAlH4 (3) PCC (4) KMnO4

69. ; Product of the above reaction is–

(1) Racemic (2) Diastereomer (3) Meso (4) Optically pure

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70. An optically active alcohol of formula C9H12O2 produced the following compound when refluxed with KMnO4–

The original compound showed these properties also:

What is structure of (A)

(1) (2) (3) (4) both 1 and 2

71. In which of the following group, each member gives positive iodoform test–
(1) methanol, ethanol, propanone (2) ethanol, isopropanal, methanal
(3) ethanol, ethanal, isopropyl alcohol (4) propanal, propanol–2, propanone

72.

Identify the position where the above acetylation reaction take place–
(1) a (2) b (3) c (4) d
73. Identify the reagents (1–4), required for the transformations shown and arrange them in correct order–

(1) LAH (LiAlH4) (2) OsO4 (3) NaIO4 (4) NaBH4

(1) 1  3  4  2 (2) 2  3  1  4 (3) 2  1  3  4 (4) 1  2  3  4

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74.

When Grignard reagent reacts with (B) product (D) will obtained–
Reactant (A) of the above reaction is–

(1) (2) (3) (4)

75. Select the correct statement–

(1) Solvolysis of (CH3)2C=CH–CH2–Cl in ethanol is over 6000 times greater than alkyl chloride (25°C)
(2) CH3–CH=CH–CH2–OH when reacts with HBr give a mixture of 1–bromo–2–butene and 3–bromo 1–butene
(3) When solution of 3–buten–2–ol in aqueous sulphuric acid is allowed to stand for one week, it was found to contain both
3–buten–2–ol and 2–buten–1–ol
(4) All of these
76. What is the major organic product of the following sequence of reactions–

(1) (2) (CH3)2CHCH2CH2OH

(3) (4) (CH3)2CHCH2CH2CH2OH

77. 0.092 g of a compound with the molecular formula C3H8O3 on reaction with an excess of CH3MgI gives 67.00 mL of methane
at STP. The number of active hydrogen atoms present in a molecule of the compound is–
(1) one (2) two (3) three (4) four
78. The final product in following reaction is–

(1) (2) (3) (4)

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OH

P.C.C.
 (P) HO OH (i) CH MgBr
3
(Q)  (R) 
 (S)
Lucas reagent
79. (2mole) (1 mole) (ii) H
CH2OH

The product(s) show white ppt.

(1) Immediate (2) After 5 min.
(3) No ppt. at room temperature (4) No reaction
OH

PCC
80. 
(X) Major

CH3 OH

OH
O O OH

(1) (2) (3) (4)

O

O OH

Passage- Acid catalysed conversion of 1,2–diol or vicinal diol, into carbonyl compound known as pinacol–pinacolone rearrangement.

Generally more electron donating group migrate during mechanism, migration of —H is faster because of its smaller size.

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81. What would be the major product of reaction

(1) (2) (3) (4)

82.

In this sequence of reaction final product is–

(1) (2) (3) (4)

83. Column – I Column – II

(a) Identification of 1°, 2° and 3° Alcohol (1) pcc

(b) Identification of 1°, 2° and 3° Nitroalkane (2) Oxymercuration demercuration react

(c) Formation of alcohol by anti–Markownikoff's addition (3) Cu/300°C, 

(d) Formation of alcohol by Markownikoff's addition (4) Hydroboration oxidation

(5) Victor mayer test

ANSWER-KEY
Qus. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20
Ans. 2 1 3 4 1 3 1 3 2 1 3 3 4 1 2 3 3 4 2 1
Qus. 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40
Ans. 2 1 1 1 3 2 2 3 2 3 3 1 2 3 4 2 2 2 3 4
Qus. 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60
Ans. 1 4 2 3 3 2 4 312 1 3 4 3 1 3 1 3 4 4 2 2
Qus. 61 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80
Ans. 2 1 3 1 2 2 2 2 2 4 3 2 4 1 4 4 3 1 1 3
Qus. 81 82 83(a) 83(b) 83(c) 83(d)
Ans. 3 3 135 5 4 2

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Exercise-02
1. Compound which gives alcohol on reduction is/are

O O
|| ||
(1) Me  C  Cl (2) Me  C  NH 2 (3) Me  CH  CH 2 (4) Me  C  OC  Me
|| || \ /
O
O O
dil. H SO H
2. In the reaction sequence, CaC2 H
2O
 A  
2
4  B 
2
C, true about the product C is
2 Ni
Hg

(1) give yellow ppt. with NaOI (2) its final oxidation product is carbonyl compound

(3) its final oxidation product is CO2 and H2O (4) its final oxidation product is CH3COOH

3. Which can be cleaved by HIO4?

O O OH OH O O
|| || | | || ||
(1) CH3 CH2 CCH2 CCH3 (2) CH3 CH CHCH2 CH3 (3) (4) CH3 CCH2 CHCH2 CCH3
|
OH
4. HBO, oxymercuration-demercuration and acid catalysed hydration will not give same product in

(1) (2) (3) (4)

5. Diethyl ether reacts with PCl5 to form

(1) Ethyl chloride (2) Phosphorous oxy trichloride

(3) Ethenol (4) Ethene

6. Select the correct synthesis products

BH ·THF H O , OH 
(1) 3 2 
2
 NaOH
 

Hg ( OAc ) NaBH
(2)    4  NaOH
2    
H 2O


(3) O OI
  CHI3


(4)

7. Anhydride of alcohol is -

(1) Ether (2) Aldehyde (3) Alkyl hydrogen sulphur (4) Alkene

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8. Lucas test is used to make distinction between 1°, 2° and 3° alcohols

ROH + HCl anhydrous ZnCl

   2  RCl  + H2O This shows that -
conc.
White turbidity

(1) ROH behaves as a base

(2) greater the value of pKa (alcohol), greater the reactivity with conc. HCl and thus sooner the formation of white turbidity
(3) alcohol which reacts fastest with Na metal, will give turbidity at fastest rate
(4) alcohol which gives red colour during Victor Mayor test, will give turbidity at slower rate then those giving blue or white
colour during Victor Mayor test.
9. Which is/are correct statements?
CH3 CH3
CH3OH
C—C H2SO4

(1) H O CH3

nucleophile attacks here when epoxy linkage is cleaved

CH3 CH3
NaOH
(2) C—C CH3OH
H O CH3

nucleophile attacks here when epoxy linkage is cleaved

O
NaBH4 H+
(3) This is only affected in reduction to 2° alcohol  
 (4) R–C–OH + H–O–R
CH3OH

These bonds undergo cleavage in the reaction

10. 3-Methyl-3-hexanol can be prepared by

(1) CH3MgI and 3-Hexanone, followed by hydrolysis (2) C2H5MgI and 2-Pentanone, followed by hydrolysis
(3) C3H7MgI and 2-Butananone, followed by hydrolysis (4) C4H9MgI and propanone, followed by hydrolysis
11. Which of the following will get oxidised by Br2 / KOH into carboxylic acid?

(1) CH3–CH2–OH (2) CH CH3 (3) CH2OH (4)

OH
12. Methanol can be distinguished from ethanol by
(1) Heating with I2 and alkali (2) Treating with schiff’s reagent
(3) Treating with CrO3 solution in dil. H2SO4 (4) Treating with Lucas reagent
13. For the reactions shown below, identify the correct statement(s) with regard to the products formed:

 NaOMe / MeOH
(i) MeOH
 ,H
 P (ii)     Q

(1) P and Q are identical (2) P is racemic and Q is optically active

(3) P and Q are positional isomers (4) both are optically active
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Tilden NH NaNO
14. C2H5NH2  (i) 
3  (ii)  
2  (iii). The product (iii) can be
reagent HCl

(1) Alcohol (2) Ether (3) Alkyl chloride (4) Alkyl nitrite

15. Consider the compound A Select the correct statement(s)

(1) It is more acidic than CH3OH

O
||
(2) It is more acidic than CH COH
3

(3) It reacts very fast with Lucas reagent

(4) It is a diacid base

16. The ether O – CH2 when treated with conc. HI produces

(1) CH2 – l (2) CH2OH

(3) l (4) OH

17. Alkan-1,2-diols are oxidised into two fragments when treated with –
(1) periodic acid (2) lead tetraacetate (3) anhydrous ZnCl2 (4) conc. H2SO4
18. Which of the following reagents or process are suitable to distinguish MeOH and EtOH ?
OH
COOH & H

(1) NaOI (2)

(3) anhydrous ZnCl2 + conc. HCl (4) Victor Mayor’s process

19. In which of the following reaction(s) the major organic product(s) will respond to haloform reaction.
Ph CH3
Aq. AgNO3 H O  / Hg 2 
(1) H3C C2H5 Product (2) Ph 3

 Product
H+/ CH3 
OH I
O
H
heat
(3) Ph O 
 Product (4)  Product
Cu / 300ºC
OH 
HO CH3
20. Which of the following reactions give alcohols as the products
1)B H / THF 2 1)Hg(oAc)  THF / H O
2 
(1) R  CH  CH 2 
2 6

 (2) R  CH  CH 2 

2)H 2O2 / OH 2)NaBH4 / OH

1)H  ,H O Aq.KOH
(3) R  CH  CH 2 
2 
(4) R  CH 2  CH 2  x 

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21. CH 3  CH  CH  CH 2 Re agent R Alcohol which is true about alcohol and R?

  
|
CH 3

Alcohol Reagent

CH 3  CH  CH 2  CH 2OH
|
(1) CH 3 B2H6 , H2O2 / NaOH

(2) CH 3  CH  CH  CH 3 Hg(OAc)2, H2O / NaBH4

| |
CH 3 OH

OH
|
(3) CH  C  CH CH B2H6 , H2O2 / NaOH
3 2 3
|
CH 3

OH
|
CH 3  C  CH 2 CH 3
(4) | dil. H2SO4
CH 3
22. Match the following:
Reaction Mechanism


H3O
(A)  (p) change in number of carbon in cycle
heat

(B) HIO (q) Pinacol rearrangement

4 


(C) H
 (r) Oxidative bond cleavage
heat

H O
(D) 
3
 (s) Ketone as product
heat

23. Match the column:

Column I Column II
(A) Identification of 1°, 2°& 3° Alcohols (p) Oxymercuration demercuration
(B) Identification of 1°, 2°& 3° Nitro alkanes (q) Cu/300° heat
(C) Formation of alcohol by anti Markovnikov's (r) Victor Mayer's test
addition of H2O
(D) Formation of alcohol by Markovnikov's addition (s) Hydroboration oxidation
(t) Lucas test

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24. Match the following
Column I Column II

CH2OH CH3 OH
H2SO4
(A) (p)

CH2OH

P, I2
(B) (q)

O CH2–I

(C) 3 H O (r)
 CH3MgI 


25. Match the column –

Column I Column II

CH3
CH3 |
| H 3O
(A) (p) CH 3  C  OH is one of the product of the reaction
CH3  C  O  CH  CH 3 |
| | CH3
CH3 CH 3

CH3 OH
H3O
(B) O C CH3 (q) is one of the product of the reaction
CH3

CH3
H3O
(C) O CH (r) CH 3  CH  OH is one of the product of the reaction
CH3 |
CH3

ANSWER SHEET
Qus. 1 2 3 4 5 6 7 8 9 10
Ans. 1 14 2 124 12 13 1 124 1234 123
Qus. 11 12 13 14 15 16 17 18 19 20
Ans. 12 1 34 1234 12 14 12 12 134 1234
Qus. 21 22(A) 22(B) 22(C) 22(D) 23(A) 23(B) 23(C) 23(D) 24(A)
Ans. 124 qs rs p s qrt r s p q
Qus. 24(B) 24(C) 25(A) 25(B) 25(C)
Ans. r p pr pq qr

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Exercise-03 (CollectionofPreviousYearIIT-JEEQuestions)
1. 1-propanol & 2-propanol can be best distinguished by: [JEE 2001]

(1) Oxidation with alkaline KMnO4 followed by reaction with Fehling solution

(2) Oxidation with acidic dichromate followed by reaction with Fehling solution

(3) Oxidation by heating with copper followed by reaction with Fehling solution

(4) Oxidation with concentrated H2SO4 followed by reaction with Fehling

2. Select the correct order of boling point of following compound [JEE 2002]

CH3CH2CH2CH2OH CH3CH2CH2CHO CH3CH2CH2COOH

1 2 3
(1) 1 > 2 > 3 (2) 3 > 1 > 2 (3) 1 > 3 > 2 (4) 3 > 2 >1

C H O  Na  ( excess )
3. OH + C2H5I      
2 5 [JEE 2003]
C 2 H5OH ( anhydrous)

(1) OC2H5 (2) I

(3) C6H5OC6H5 (4) C2H5OC2H5

4. On acid catalysed hydration, 2-Phenyl propene gives:
[JEE 2004]
(1) 3-Phenyl-2-propanol (2) 2-Phenyl-1-propanol
(3) 1-Phenyl-3-propanol (4) 2-Phenyl-2-propanol
5. Which is the best reagent to convert cyclohexanol into cyclohexene. [JEE 2005]
(1) conc. HCl (2) conc. HBr (3) conc. H3PO4 (4) HCl + ZnCl2

6. In the following reaction sequence, the correct structures of E, F and G are

O O

Heat I
2 [F]  [G]

[E] 
Ph * OH NaOH
(* implies 13C labelled carbon)

O O O O
(1) E = F= G = CHI3 (2) E = F= G = CHI3
* * – + – +
Ph Ph ONa Ph * Ph ONa
CH3 CH3

O O O O
* *
(3) E = F= G = CHI3 (4) E = F= G = CH 3I
– + – +
Ph * Ph ONa Ph * Ph ONa
CH3 CH3

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7. Match the reactions in Column I with appropriate options in Column II- [JEE -2010]

Column I Column II

(A) (p) Racemic mixture

(B) (q) Addition reaction

(C) (r) Substitution reaction

(D) (s) Coupling reaction

(t) Carbocation intermediate

8. Match the chemical conversions in List I with the appropriate reagents in List II and select the correct answer using the code
below the lists. [JEE-Advance -2013]

List-I List-II

(P) (1) (i) Hg(OAc)2; (ii) NaBH4

(Q) (2) NaOEt

(R) (3) Et-Br

(S) (4) (i) BH3; (ii) H2O2/NaOH

Codes:
P Q R S
(1) 2 3 1 4
(2) 3 2 1 4
(3) 2 3 4 1
(4) 3 2 4 1

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9. Consider all possible isomeric ketones, including stereoisomers of MW = 100. All these isomers are independently reacted

with NaBH4 ( NOTE : stereoisomers are also reacted separately). The total number of ketones that give a racemic product

(s) is/are-

[JEE-Advance -2014]

10. The acidic hydrolysis of ether (X) shown below is fastest when

[JEE-Advance -2014]

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

(B) one phenyl group is replaced by a para–methoxyphenyl group.

(C) two phenyl groups are replaced by two para–methoxyphenyl groups

(D) No strucuture change is made to x.

ANSWER SHEET
Qus. 1 2 3 4 5 6 7(A) 7(A) 7(C) 7(D) 8
Ans. 3 2 4 4 3 3 rs t pq r 1
Qus. 9 10
Ans. 5 3

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Exercise-04 (Collection ofPreviousYear AIEEE Questions)

1. An ether is more volatile than alcohol having the same molecular formula. This is due to [AIEEE-2003]

(1) intermolecular hydrogen bonding in alcohols (2) dipolar character of ethers

(3) alcohols having resonace structures (4) intermolecular hydrogen bonding in ethers.

2. During dehydration of alcohols to alkenes by heating with conc. H2SO4, The initiation step is [AIEEE-2003]

(1) formation of an ester (2) protonation of alcohol molecule

(3) formation of carbcation (4) elimination of water

3. Acetyl bromide reacts with excess of CH3MgI followed by treatment with a saturated solution of NH 4Cl gives -

[AIEEE-2004]

(1) 2-methyl-2-propanol (2) acetamide (3) acetone (4) acetyl iodide

4. Phenyl magnesium bromide reacts with methanol to give– [AIEEE -2006]

(1) a mixture of phenol and Mg(Me)Br (2) a mixture of anisole and Mg(OH)Br

(3) a mixture of benzene and Mg(OMe)Br (4) a mixture of toluene and Mg(OH)Br

5. Consider the following reaction: [AIEEE-2011]

C2H5OH + H2SO4.  Product

Among the following, which one cannot be formed as a

product under any conditions?

(1) Ethylene (2) Acetylene (3) Diethyl ether (4) Ethyl-hydrogen sulphate
6. 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]

(1) Secondary alcohol by SN1 (2) Tertiary alcohol by SN1

(3) Secondary alcohol by SN2 (4) Tertiary alcohol by SN2

7. In the reaction, [JEE-Main- 2014]

LiAlH4 PCl5 Alc. KOH

CH3COOH A B C , the product C is :
(1) Ethylene (2) Acetyl chloride (3) Acetaldehyde (4) Acetylene

8. The most suitable reagent for the conversion of R – CH2 – OH  R – CHO is : [JEE-Main- 2014]
(1) CrO3 (2) PCC (Pyridinium Chlorochromate)
(3) KMnO4 (4) K2Cr2O7

ANSWER-KEY
Qus. 1 2 3 4 5 6 7 8
Ans. 1 2 1 3 2 2 1 2

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