Ghanshyam Classes

IT IS A PAPER OF ORGANIC CHEMISTRY

JEE main - Chemistry
Time Allowed: 34 minutes
Maximum Marks: 272

General Instructions:

Dhnag Se Karna hai!

1. Complete the following chart.

[4]

SE M
a)
P =  , Q =  ,  R = 
YA b)
P =  , Q =  , R = 

S
SH
c) d)
P =  , Q =  , R =  P =  , Q =  , R = 
NA

2. The correct stability order of the following resonance structure is [4]

AS

+ −

I. H 2C = N = N

+ −

II. H 2C − N = N
GH

− +

III. H
CL

2  C − N ≡ N

− +

IV. H 2C − N = N

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

c) (I) > (II) > (IV) > (III) d) (I) > (III) > (II) > (IV)
3. Predict the most stable carbocation amongst the following. [4]

a) b)

c) d)

[4]

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 4. The radical,   is aromatic because it has:

a) 7 p-orbitals and 7 unpaired electrons b) 6 p-orbitals and 6 unpaired electrons

c) 6 p-orbitals and 7 unpaired electrons d) 7 p-orbitals and 6 unpaired electrons

5. Which of the following is an electrophilic reagent? [4]

a) BF3 b) NH3

c) RO- d) ROH

6. The decreasing order of stability of following cations is

[4]

SE M
a) P > S > Q > R b) P > R > Q > S

7.
c) P > Q > R > S
YA
The order of decreasing stability of the following cations is:
+
d) S > R > Q > P
[4]

i. C H C HC H3

S
3
SH
+

ii. C H 3 C HOC H3

iii. C H3 C HC OC H3
NA

a) i > iii > ii b) iii > ii > i

AS

c) i > ii > iii d) ii > i > iii

+

8. C H3 − C = N − OH −→
−
H

C H3 − C = O is an illustration for ________ reaction. [4]

GH

| |
CL

Ph NH Ph

a) isomerization b) rearrangement

c) β-elimination d) electrophilic addition

9. Which of the following carbocations is expected to be most stable? [4]

a) b)

c) d)

10. The IUPAC name of the following compound is

[4]

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 a) 2-bromo-5-hydroxybenzonitrile b) 2-cyano-4-hydroxybromobenzene

c) 4-bromo-3-cyanophenol d) 6-bromo-3hydroxybenzonitrile

Br2 ,  H2 O
[4]
11.  −−−−−→

a) b)

SE M
c) d)
YA
12. How many chiral centers are present in cholesterol?
[4]

S
SH
NA
AS

a) 5 b) 9

c) 7 d) 8
GH
CL

Mg [4]
13. −−−−−→  Product:
 dry ether 

a) b)

c) CH3 - CH = CH2 d)

14. Which one of the following compounds undergoes hydrolysis most readily by aq. NaOH to furnish [4]
corresponding phenol?

a) b)

c) d)

3 / 13
15. Pick up an incorrect statement from the following: [4]

a) The displacement of hydrogen atom from b) Reactivity of halogens towards alkanes

any hydrocarbon on dehalogenation follows decreases in the order, I2 > Br2 > Cl2 > F2.
the order, 3° H-atom > 2° Hatom > 1° H-
atom > H-atom of methane > arylic H-atom

c) The order of reactivity of carbocations d) The order of reactivity of halogen acids with
(from alcohols) towards halogen acids is,
alcohols is HI > HBr > HCl > HF.

SE M
16. Isobutyl magnesium bromide with dry ether and ethyl alcohol gives: [4]

a) C H 3 C H C H3
|

C H3
& CH3CH2OMgBr
YAb) C H3 C H C H2 OH
|

C H3
& CH3CH2MgBr

S
c) C H & Mg(OH)Br d) & MgBr(OC2H5)
SH
3 C H C H = C H2 C H3 C H C H3
| |

C H3 C H3

17. p-hydroxybenzophenone upon reaction with bromine in carbon tetrachloride gives [4]
NA

a) b)
AS
GH

c) d)
CL

[4]
18.

In the above reaction, maximum Saytzeff product will be obtained where X is:

a) -I b) -F

c) -Cl d) -Br
19. An organic compound A (Molecular formula C6H12O4) on treatment with Na metal liberates H2 gas and on [4]

treatment with HIO4 gives 2 moles of CH3CHO, HCOOH(l mole) and CO2 (1 mole). Find out structure of A.

a) b)

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 c) d)

SE M
YA
S
SH

20. In Williamson’s synthesis ethoxy ethane is prepared by [4]

a) Passing ethanol over heated alumina b) Heating ethanol with dry Ag2O
NA
AS

c) Heating sodium ethoxide with ethyl bromide d) Treating ethyl alcohol with an excess of
conc. H2SO4 at 430-440 K

21. In the reaction the products are: [4]

GH
CL

a) b)

c) d)

22. The reaction products of C6H5OCH3 + HI −

→ is:
[4]

a) C6H6 + CH3OH b) C6H5I + CH3OH

c) C6H5CH3 + HOI d) C6H5OH + CH3I

23. Select the major product of following reaction:

[4]
⊖

C H3 C H2 O

 −−−−−−→

a) b)

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 c) d)

[4]
24.  on dehydration gives:

a) b)

c) d)

SE M
25. On heating glycerol with KHSO4/Δ, a compound is obtained, which has a bad odour. The compound is: [4]

a) Allyl alcohol
YA b) Formic acid

c) Methyl isocyanide d) Acrolein

S
SH
Mg−Hg Dil . H2 SO4

26. 2Ph − C − CH3 −−−−→−−−−−−→ Product, ​

[4]
||
H2 O

The main product is:

NA

a) CH b) Ph
AS
3 − C − C − C H3
|
|| ||
Ph − C − C − C H3
O O
| ||

CH3 O
GH

c) Ph − C − C − Ph d) Ph
CL

|
|| ||
Ph − C − C − CH3
O O
|| |

O CH3

27. The reaction of phenol with benzoyl chloride to give phenyl benzoate is known as: [4]

a) Schotten-Baumann reaction b) Claisen reaction

c) Gatterman-Koch reaction d) Reimer-Tiemann reaction

CH3

|
CH3

|
[4]
X

28. H3 C − C − CH = CH2 −
→ H3 C − C − CH − CH3 , X can be:
| | |

CH3 CH3 OH

a) BH /THF, H O /OH- b) H O+
3 2 2 3

c) Hg(OAc)2/NaBH4,NaOH d) All of these

29. Find the incorrect reactions from the following.

[4]

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 a) i, iii b) ii, iii

SE M
c) i, iv d) ii, iv

30.
P Br
⊕ ⊖

K C N

 −−→ −−−−→ final product. YA [4]

a) b)

S
SH

c) d)
NA
AS

31. The C - O - C bond angle in methoxymethane is approximately ________. [4]

a) 120° b) 108°
GH
CL

c) 104° d) 110°
32. In Liebermann nitroso test: [4]

a) none of these b) aniline reacts with nitrous acid

c) phenol reacts with NaNO2 + HCl or HNO2 d) phenol and aniline reacts with NaNO2 +
HCl
33. Which of the phenol derivative is most acidic? [4]

a) b)

c) d)

34. The oxygen atom in alcohols is in ________ hybridization. [4]

7 / 13
 a) sp3d b) sp2

c) sp3 d) dsp2

[4]
35.  is changed into   by:

a) i. Na2Cr2O7 + H2SO4 b) i. CrO3

ii. CH3CH2MgBr, H3O+ ii. CH3CH2MgBr, H3O+

c) i. KMnO4 d)
i. Cu, 300oC
ii. CH3CH2MgBr, H3O+ ii. CH3CH2MgBr, H3O+

36. In the given reaction,

[4]

SE M
⊖ ⊕
B 2 H6 T sC l M e3 C O K

 −−−−−−→ −−−→ −−−−−−−→ (B)

⊖
H2 O2 , OH

The product B is:

a) a positional isomer of A
YA
b) chain isomer of A

c) reduced product of A d) identical to B

S
SH
37. Which of the following reagents cannot be used for the oxidation of 1° alcohol to aldehyde? [4]

a) PCC b) KMnO4
NA

c) Collin’s reagent d) MnO2

AS

38. The miscibility of ethers in aqueous solvents is due to its ability to form ________ with water. [4]

a) covalent bond b) intramolecular hydrogen bond

GH
CL

c) intermolecular hydrogen bond d) ionic bond

39. Glycerol has ________. [4]

a) one primary and two secondary -OH groups b) three secondary -OH groups

c) three primary -OH groups d) one secondary and two primary -OH groups
40. Arrange the following alcohols in the decreasing order of their reactivity towards the Lucas reagent?
[4]

a) iii > i > ii > iv b) i > iii > ii > iv

c) ii > i > iii > iv d) iv > iii > ii > i

[4]
41.

The final product is:

a) b)

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 CH3 − CH − CH2 CH2 OH CH3 − CH − O − CH2 − CH3
| |

C H3 C H3

c) none of these d) CH3 − O − CH − CH2 − CH3

|

C H3

[4]

42.

Arrange the above phenols in increasing order of Ka value:

a) III < I < II b) I < III < II

c) III < II < I d) I < II < III

SE M
43. An alkene obtained by the dehydration of an alcohol (A), on ozonolysis gives two molecules of acetaldehyde for [4]
every molecule of alkene. The alcohol (A) is:

a) CH3CH2CH2OH
YA b) C H3 C H2 CH C H3
|

OH

S
SH
c) CH3CH2OH d) CH3CH = CHCH2OH

44. At low temperature, phenol reacts with Br2 in chloroform to form ________ as the major product. [4]

a) 2, 4, 6-tribromophenol b) 2-bromophenol
NA
AS

c) 4-bromophenol d) 2-bromophenol
45. The synonym for water gas when used in the production of methanol is [4]

a) Laughing gas b) Syn gas

GH
CL

c) Natural gas d) Fuel gas

46. The conversion of cyclohexanol to 1-propylcyclohexene can be best carried out by ________. [4]

a) K Cr O /H+, LiAlH , H O/H+ b) Acidic KMnO4, NaBH4, Heat with H2SO4

2 2 7 4 2

c) PCC, C H MgBr/dry ether, H O+, Δ/Al O d) K Cr O /H+, C H MgBr, Heat with H SO

3 7 3 2 3 2 2 7 2 5 2 4

47. When ethylene glycol is heated with oxalic acid in the presence of cone. H2SO4, the product formed is: [4]

a) b)

c) d)

48. 1-propanol and 2-propanol can be best distinguished by [4]

a) oxidation with concentrated H2SO4 b) oxidation by heating with copper followed

followed by reaction with Fehling solution by reaction with Fehling solution

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 c) oxidation with acidic dichromate followed d) oxidation with alkaline KMnO4 followed by
by reaction with Fehling solution reaction with Fehling solution
49. The gas evolved on heating CH3MgBr in methanol is: [4]

a) HBr b) Propane

c) Methane d) Ethane
50. Amongst the following compounds, predict the one which is the least acidic? [4]

a) m-Cresol b) o-Cresol

c) Phenol d) p-Cresol
51. The molecule shown is a ________ alcohol because ________
[4]
C H3 − C H2 C H C H2 C H3
|

OH

SE M
a) secondary, the carbon bonded to the -OH b) primary, its -OH group is on the central
group is bonded to two other carbons carbon

c) primary, it has one -OH group

YA d) secondary, each group bonded to the
hydroxyl carbon contains two carbon atoms
52. The enol form of acetone, after treatment with D2O, gives [4]

S
SH
a) OD

|
b) OD

H3 C -  C  = C H2 D2 C =  C  - C D3

c) O
d) OH
NA

|| |

D3 C -  C  = C D3 H2 C =  C  - C H2 D
AS

[4]
53. The hydrolysis of  in aqueous acetone gives:

GH
CL

where

a) Only M b) K and L

c) Only K d) L and M
54. A solution of phenol in chloroform, when treated with aqueous NaOH, gives compound P as a major product. [4]
The mass percentage of carbon in P is ________. (to the nearest integer) (Atomic mass: C = 12; H = 1; O = 16)
55. The increasing order of diazotisation of the following compounds is:
[4]

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 a) (A) < (D) < (C) < (B) b) (A) < (D) < (B) < (C)

c) (D) < (C) < (B) < (A) d) (A) < (B) < (C) < (D)
56. The tests performed on compound X and their inferences are : [4]

Test Inference

SE M
(a) 2, 4 - DNP test Coloured precipitate

(b) Iodoform test Yellow precipitate

(c) Azo-dye test

Compound 'X' is
YA No dye formation

S
a) b)
SH
NA
AS

c) d)
GH
CL

57. In a set of reactions propionic acid yielded a compound D:

[4]
SOCl2 NH3 KOH

 −−−→ B −−−→ C −−−→ D

Br2

The structure of D would be:

a) b)

c) d)

58. The preferred set of reagents required for the following conversion is ________.
[4]
?

CH3(CH2)3I → CH3(CH2)3NH2

11 / 13
 a) alc. KCN, Sn/conc.HCl b) NH3, 373 K, sealed copper tube

c) alc. AgNO2, d) NaN3,

H NO2
- 5°C
Na

0 EtOH

59. The total number of sigma bonds present in the product X is ________.
[4]
+
H (pH ≈4.5)

Benzenediazonium chloride + N, N-Dimethylaniline −−−−−−−→ X (Coloured compound)

273K−278K
O

||
[4]
60. What is the IUPAC name of H - C - CH2 - CH2 - OCH3?

a) 3-Methoxypropanal b) Methoxypropanal

c) 2-Methoxypropanal d) 2-Formylmethoxyethane
61. The CORRECT structure of the product A formed in the following reaction is ________.
[4]

H2 gas.1 (atmosphere)

 −−−−−−−−−−−−−→ A

SE M
P d/carbon. ethanol

a)
YA b)

S
SH

c) d)
NA
AS
GH
CL

62. The major aromatic product C in the following reaction sequence will be:
[4]
HBr
(e xc e ss) (i) KOH (Alc.) O3

 −−−→ (A) −−−−−−−−→ B −−−−−−→ C

 +   + 
Δ (ii) H Zn/H3 O

a) b)

c) d)

63. Which of the following is an example of aldol condensation reaction? [4]

a) b) NaOH

 −−−−→  Ph -
Δ

CH2 - OH

c) d)

12 / 13
64. Find out correct sequence of reagents for the following conversion.
[4]
O O

|| ||

P h − C − OH → P h − C − H

a) b)
O SOC l2 ,  H2

||
P d, BaSO4
C H3 − C − C l,  LiAlH4

c) CH2N2, NaBH4 d) PCI5, CH3MgBr

65. Which of the following is correct?

[4]

a) b)

SE M
c)
YA d)

[4]

S
SH
66.

Major product is
NA
AS

a) b)
GH
CL

c) d)

67. Assertion (A): Pentan-2-one can be distinguished from pentan-3-one by iodoform test.
[4]
Reason (R): Former is methyl ketone while the latter is not.

a) Both A and R are true and R is the correct b) Both A and R are true but R is not the
explanation of A. correct explanation of A.

c) A is true but R is false. d) A is false but R is true.

68. Among the following the number of reaction(s) that produce(s) benzaldehyde is
[4]

13 / 13