PREPARATION:BY REDUCTION

1. The suitable reagent to convert alkane of the aldehyde and ketone is -

(A) LiAIH4 (B) HI + P (C) Red P (D) H2SO4

2. Which one of the following is reduced with amalgmated zinc and hydrochloric acid to give the
corresponding hydrocarbon-
(A) Ethyl acetate (B) Acetic acid (C) Acetamide (D) Butan-2-one
3. Acetone Clemmensen reduction forms-
(A) Propane (B) Propene (C) Propanol (D) Propyne
4. Wolff-Kishner reaction is used for the reduction of -
(A) Olefines (B) Carboxylic acid
(C) Nitro compound (D) Carbonyl compounds
5. Phenyl methyl ketone can be converted to ethylbenzene in one step by which of the following reagents ?
(A) NaBH4 (B) CH3 MgI (C) LiAH4 (D) Zn  Hg  /HCl

KOLBE’S-ELECTROLYSIS
6. On electrolysis of sodium acetate H2 gas is evolved at cathode, C2H6 is at anode. Then reaction is known
as-
(A) Frankland (B) Kolbe synthesis (C) Clemmension (D) wolf-kishner
7. What are all the possible products in Kolbe‘s Electrolysis of sodium salt of propanoic acid at anode:
(A) Alkane and ester (B) Alkane, alkene and hydrogen
(C) Alkane, alkene, ester and hydrogen (D) Alkane, alkene and ester
8. During the preparation of ethane by Kolbe‘s electrolytic method using inert electrode the pH of the
electrolyte:
(A) increases progressively as the reaction proceeds
(B) decrease progressively as the reaction proceeds
(C) remain constant throughout the reaction
(D) none
9. KOOC CH2 CH2 CH(COOK)CH2 CH2 COOK on electrolysis gives
(A) CH2  CHCH2 CH  CH2 (B)

(C) (D)
10. Which of the following can not be prepared by Kolbe‘s synthesis.
(A) CH4 (B) C4H10 (C) C2H6 (D) H2
11. Ethane is produced during the electrolysis of potassium salt of
(A) succinic acid (B) malonic acid (C) acetic acid (D) fumaric acid

WURTZ REACTION
12. Alkane is prepared by -
(A) Wurtz (B) Reduction to alkyl halide
(C) By Grignard reagent (D) All of the above
13. When ethyl iodide and propyl iodide react with Na in the presence of ether, they form -
(A) One alkanes (B) Two alkanes (C) Three alkanes (D) Four alkanes

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14. A sample of 1.79 mg of a compound of molar mass 90 g mol –1 when treated with CH3Mgl releases 1.34
ml of a gas at STP. The number of active hydrogen in the molecule is
(A) 1 (B) 2 (C) 3 (D) 4.

BY ORGANOMETALLIC COMPOUNDS
15. Which of the following alkyl halides is not suitable for Corey-House synthesis of alkanes?
(A) CH3 I (B) (C) (D)

16. Which of the following is known as Gilman reagent ?

(A) RMgX (B) R 2 CuLi (C) R 2 Zn (D) ZnCl 2  conc.HCl

17. Propane can be best prepared by the reaction

(A) CH3CH2 I  CH3I  Na 
Et O
 2
(B) CH3CH2 COONa  CH3COONa H O
electrolysis
 2

(C) CH 3 CH 2 Br   CH 3  2 CuLi 

Et 2 O
 (D) CH 3 CH 2 CH 2 CH 2 COONa 
NaOH
CaO , heat


18. The treatment of C 2 H 5 Mgl with water produces

(A) Methane (B) Ethane (C) Ethanal (D) Ethanol.

PHYSICAL PROPERTIES OF ALKANES

19. Decreasing order of melting point of given alkanes

I II III
(A) III > II > I (B) III > I > II (C) I > II > III (D) I > III > II
20. Arrange (I) Methane, (II) Ethane, (III) Propane, and (IV) n–Butane in decreasing order of melting point:
(A) IV > II > I > III (B) IV > I > II > III (C) IV > III > II > I (D) IV > III > I > II
21. Which hydrocarbon is solid at normal temperature -
(A) CH4 (B) C7H8 (C) C8H18 (D) C20H42

22. Which of the following has the highest boiling point -

(A) n-octane (B) neooctane
(C) Isooctane (D) 2, 2-Dimethyl pentane
23. In order to overcome angle strain, cyclohexane acquires.
(A) Square planar structure (B) Planar structure
(C) Puckered ring structure (D) Pyramidal structure
24. The compound with the highest boiling point is
(A) n-hexane (B) n-pentane
(C) 2, 2-dimethylpropane (D) 2-methylbutane
25. When the boiling points of the first ten normal alkanes are plotted the graph looks like:

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

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 CHEMICAL PROPERTIES
FREE RADICAL SUBSTITUTION REACTION OF ALKANE
26. The reaction conditions leading to the best yield of C2 H5Cl are
(A) C 2 H6  excess   Cl 2 
UV
light
 (B) C 2 H 6  Cl 2 
dark
room temp.

(C) C 2 H6  Cl 2  excess  

UV
light
 (D) C 2 H6  Cl 2 
UV
light


27. Which of the following reactions has zero activation energy?


(A) CH 4  Cl  
 C H 3  HCl (B) Cl  Cl 
hv
 2Cl 
(C) CH3  CH3 
 CH3  CH3 (D) CH3  Cl  Cl 
 CH3  Cl  Cl 
28. Which one is the correct energy profile for Cl   Cl  
 Cl 2

(A) (B) (C) (D) All of these

29. The relative reactivity of 1ºH, 2ºH and 3ºH in bromination reaction has been found to be 1 : 82 : 1600
respectively. In the reaction,

The percentage yield of (A) and (B) are expected to be:

(A) 99.4%, 0.6% (B) 50%, 50% (C) 0.6%, 99.4% (D) 80%, 20%
30. The relative reactivity of 1º, 2º and 3º hydrogens in chlorination reaction has been found to be 1: 3.8 : 5.
In the reaction,

The ratio of the amount of the product (A), (B), (C) and (D) is expected to be:
(A) 1 : 3.8 : 5 : 1 (B) 3 : 7.6 : 5 : 6 (C) 3 : 7.6 : 5 : 3 (D) 1 : 7.6 : 5 : 1
31. Consider the following reaction:

Identify structure of (X) among following:

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

32. Select the chain propagation steps in the free radical chlorination of methane
(I) Cl2  2Cl (II) Cl CH4 CH3Cl + H

(III) Cl   CH 4  C H 3  HCl (IV) H Cl2 HCl + Cl


(V) CH 3  Cl 2  CH 3 Cl  Cl 
(A) II, III, V (B) I, III, V (C) III, V (D) II, III, IV

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 CH3
33. Br2/hv

Total number of possible monobromo products are (including stereoisomers)

(A) 5 (B) 8 (C) 12 (D) 14
34. A hydrocarbon with formula C8H18 gives one monochloro derivative The hydrocarbon is
(A) n-octane (B) 2-methylheptane
(C) 2, 2, 4-trimethyl pentane (D) 2, 2, 3, 3-tetramethyl butane
35. Which of the following will retard the rate of reaction of chlorination of methane when added to the
reaction mixturewhile the reaction is in progress ?
(A) N2 (B) O 2 (C) CO2 (D)  C2 H5 4 Pb

36. Which of the following is/are the chain termination step during photochlorination of ethane?
   
(1) CH3 CH2  Cl  CH3–CH2–Cl (2) CH3 CH 2  CH 3CH 2  CH3CH2CH2CH3
   
(3) Cl  Cl Cl2 (4) Cl  H HCl
(A) 1 and 2 (B) 1 and 3 (C) 1, 2 and 3 (D) 1, 2, 3 and 4
37. The following structure has five different types of C-H bonds, marked a to e
H e H
H a H
H
H
H d H
bH
C
H c H
H
Arrange the five C-H bonds in decreasing order of their bond energy.
(A) a > b > d > e > c (B) a < c > b > d = e
(C) a > c >d > e > b (D) a > b > c > d > e
38. An isomer of C5H12 gives total six isomeric products on monochlorination. Calculate the percentage yield
of the primary monochloride which is chiral. Consider the following relative reactivity of C – H bonds for
chlorination.
Degree of C – H 1º C – H 2º C – H 3º C – H
Relative reactivity for
1 3 5
chlorination (RR)
(A) 26.8% (B) 25% (C) 30% (D) 50%
39. Among the given hydrocarbons which will produce 20 alkyl halide as the major product when treated
with Br2/hv
(I) cyclohexane (II) methylcyclopentane
(III)ethyl benzene (IV) 3–methyl heptane
(V) n–pentane.
(A) I, III, V (B) I, II, V (C) II, III, V (D) II, III, IV
40. Nitration of propane with nitric acid vapour at about 430o C is expected to yield
(A) 1-nitropropane (B) 2-nitropropane
(C) nitroethane and nitromethane (D) a mixtrue of all the above

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 COMBUSTION
41. Volume of oxygen is required for total combustion of propane -
(A) Five times of propane (B) 2 + 1/2 times of propane
(C) 2 times of propane (D) equal to propane

42. Arrange the given molecules in decreasing order of heat of combustion per carbon atom.

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

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

43. Which one of the following has lowest heat of combustion?

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

44. For the complete combustion of four litres of ethane the necessary volume of oxygen would be-
(A) 4 litres (B) 8 litres (C) 12 litres (D) 14 litres

ISOMERISATION, AROMATIZATION & OTHER REACTIONS

45. Which of the following alkane is affected by AlCl3.
(A) CH4 (B) C2H6 (C) C3H8 (D) C4H10

46. The pyrolysis of higher hydrocarbon into lower hydrocarbon, the process is called-
(A) Aromatisation (B) Cracking (C) Isomerisation (D) None
Cr2 O3  Al 2 O3
47. 600ºC
 Major Product:

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

Cr2 O3  Al 2 O3
48. 600ºC
 Major Product:

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

49. Which of the following is used for aromatization of n-hexane?

(A) AlCl3 (B) Na in liquid NH3
(C) Cr2O3/Al2O3 with heat (D) Wilkinson‘s catalyst

50. Identify the product in the following reaction:

heated with Cr2 O 3
n-heptane Product
supported on alumina at 600 o C
(A) benzene (B) toluene (C) xylene (D) cyclohexane

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 PREPARATION OF ALKENESBY DEHYDRATION OF ALCOHOLS
51. Alcohols undergo dehydration in the following sequence -
(A) 1º > 2º > 3º (B) 3º > 2º > 1º (C) 1º > 3º > 2º (D) 3º > 1º > 2º
52. Ethene is given by the following compound on dehydration -
(A) Ethyl acetate (B) C2H5OH (C) HCHO (D) 1 and 2
53. H2SO4 reacts with 3, 3–dimethyl–2 Butanol to form the compound -
(A) 3, 3 –dimethyl–2–butanol (B) 2, 3–dimethyl butene–1
(C) 2, 3–dimethyl butene–2 (D) None of these
54. Ethene can be produced from ethanol by-
(A) Dehydrohalogenation (B) Dehydrogenation
(C) Dehydration with conc. H2SO4 (D) Reduction with H
55. Formation of 2-butene as major product by dehydration of 2-butanol is according to -
(A) Markonikoff rule (B) Saytzeff rule
(C) Peroxide effect (D) Anti markonikoff rule
56. The dehydration of neo-pentanol gives
(A) CH 3  CH  CH  CH 2 (B) CH2  C  CH2  CH3
| |
CH3 CH3
(C) CH 3  C  CH  CH 3 (D) none of these
|
CH3

57. Arrange the following alkanols 1, 2 and 3 in order of their reactivity towards acid catalyzed dehydration:

(A) 1 > 2 > 3 (B) 2 > 1 > 3 (C) 2 > 3 > 1 (D) 3 > 2 > 1

Conc. H2 SO 4
58.  
 Major Product:

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


59. 
H

(P) ; (P) is

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

conc. H3 PO 4
60.  
 Major Product:

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

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 Conc. H3 PO 4
61.  
 Major Product:

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

62. n-Butyl alcohol on dehydration forms -butylene as the chief product. This happens because of the
rearrangement-
   
(A) CH3–CH2–CH2– CH2 to CH3– CH –CH2–CH3 (B) CH3–CH2–CH2– CH2 to (CH3)2CH– CH2
   
(C) CH3– CH –CH2–CH3 to (CH3)3 C (D) (CH3)3 C to CH3–CH2–CH2– CH2
OH

63. In the dehydration of, The products formed are

CH2 CH3

(I) (II) (III)

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

BY DEHYDRAHALOGENATION & DEHALOGENATION

64. Which of the following reagent is used in formation of alkene from alkyl halide -
(A) Alc. KOH + Heat (B) Aq. KOH + cold water (C) NaOH (D) LiOH
65. In dehydrohalogenations the base ( alcoholic KOH ) abstracts -
(A) The halide ion.
(B) The proton presents on the carbon next to the carbon to which the halogen is attached.
(C) The proton presents on the carbon to which the halogen is attached.
(D) The proton on the  -carbon.
66. In the elimination of reactions, that is, in the formation of alkenes, the reactivity of halogens in alkyl
halides is in the order -
(A) I> Br > Cl (B) Cl > Br >I (C) Br > Cl >I (D) None
67. Which is most easily dehydrohalogenate?

(A) I (B) II (C) III (D)all with same case

68. . The product can be:

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

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69. Consider the following reaction:

Br
Which of the following base will give the best yield of the alkane II as the major product?
(A) CH3 O  (B) C 2 H 5 O  (C) (CH3 )3 CO  (D) (C 2 H 5 )3 CO 
70. Propyl bromide on reaction with alcoholic KOH gives -
(A) Propane (B) Propene (C) Butane (D) Acetylene
71. Which of the following compound undergoes dehydrochlorination most easily when treated with
alcoholic KOH -
(A) CH 3  CH  CH 2 Cl (B) CH3  CH  CH2 Cl (C) CH3 – CH2 – CH2Cl (D) (CH3)3C – Cl
| |
CH3 Cl
72. In the sequence of reactions,
PCl 5
CH3CH2CH2OH   A alc.
KOH
B
the product B is -
(A) Propyne (B) Propylene (C) Propane (D) Propanol
73. Consider the following reaction
(CH3 )3 CCH2  C(CH3 )2 
base

|
Br
The major alkene product is -

(A) (CH3 )3 CCH  C(CH3 )2 (B) (CH3)3

CH3

(C) (CH3)2C = C – CH(CH3)2 (D)

74. Which of the following statements concerning E2 reactions of alkyl halide is true?
(A) The rate of an E2 reaction depends only on the concentration of alkyl halide.
(B) The rate of an E2 reaction depends only on the concentration of the base.
(C) The C—H bond and the C—X bond (X = halogen) bond are broken in the same step.
(D) Alkyl chlorides generally react faster than other alkyl halides
75. For the reaction:
Br
+CH HCOH
2 H5 OH
ONaC 
CH3 CH
CH 2ONa
3 2
2 5

the major product is formed by:

(A) SN1 reaction (B) SN2 reaction (C) an E1 reaction (D) an E2 reaction
76. Which of the following reaction will undergo elimination reaction and an alkene (major) will be formed
in the products
Me
Br N+ ..


HO O H/ 
(A) 2
(B)  

Br OH

alc  KOH
(C)  
 (D) 
conc.H 2SO 4



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77. An alkyl chloride produces a single alkene on reaction with sodium ethoxide and ethanol. The alkene
further undergoes hydrogenation to yield 2-Methylbutane. Identify the alkylchloride from the following
(A) ClCH2C(CH3)2CH3 (B) ClCH2CH2CH2CH3
(C) ClCH2CH(CH3)CH2CH3 (D) CH3C(Cl)(CH3)CH2CH3
78. The major product in the dehydrohalogenation of 2-Bromo-3, 3-dimethylbutane by E-1 mechanism
(A) 3, 3-dimethyl but-1-ene (B) 2, 3-dimethylbut-1-ene
(C) 2, 3-dimethyl but-2-ene (D) 4-methylpent-2-ene
79. 1,2-Dibromoethane reacts wtih Mg in anhydrous ether to give
(A) CH2  CH2 (B) BrCH2 CH2 MgBr
(C) BrMg  CH2  CH2  MgBr (D) CH  CH
CH3
H Br 
Nal
80. ? Product is:
Br H acetone
CH3
CH3
(A) H  (B) (C) (D)
 H
CH3

Ph
Br NaI
81. H
H Br Acetone B product B is-
Ph

H Ph H Ph H Ph H Br
(A) (B) (C) (D)
Ph H H Ph H Br H Br

82. The structural formula of the compound which yields ethylene upon reaction with zinc -
(A) CH2Br – CH2Br (B) CHBr2–CHBr2 (C) CHBr = CHBr (D) None
83. Which of the following chlorides will exclusively give 2-methylbut-2-ene on dehydrochlorination by
strong base
(A) 2-Chloro-3-methylbutane (B) 2-Chloro-2-methylbutane
(C) 1-Chloro-2-methylbutane (D) None of these

BY PYROLYTIC ELIMINATION


84.   An alkene (major)

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

85. Which ester on pyrolysis gives isobutylene -

(A) CH3 – CH2 – CH2 – O – C –CH3 (B) CH3COOCH2CH2CH3
||
O
(C) CH3COOCH2 – CH(CH3)2 (D) All the above
86. On heating n–propyldimethylamine oxide, propene is obtained. The reaction is known as -
(A) Cope reaction (B) Wurtz reaction (C) Fittig (D) None of these

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 PROPERTIES OF ALKENES
ADDITION OF HX

87. Main type of reaction given by Alkene & Alkynes -

(A) Nucleophilic addition (B) Electrophilic substitution
(C) Electrophilic addition (D) Free-radical substitution
88. The reaction: CH2 = CHCH3 + HBr  CH3CHBrCH3, is a type of -
(A) Nucleophilic addition reaction (B) Free radical addition reaction
(C) Electrophilic addition reaction (D) Electrophilic substitution reaction
89. Alkene not showing addition of HBr according to Anti-Markownikov's rule is -
(A) 1-Pentene (B) 2-Butene (C) 1-Butene (D) Propene

90. Which alkene gives same product with both Markownikoff's and anti Markownikoff's method-
(A) -Butylene (B) Propylene (C) Isobutylene (D) -Butylene
91. Action of bromine in CCl4 on ethene gives-
(A) 1, 2-Dibromo ethane (B) 4-Bromo, 2-chloro ethane
(C) Both the above (D) 1, 1, 1-tribromoethane

92. Addition of HI on double bond of propene yields isopropyl iodide & not n-propyl iodide as the major
product because addition proceeds through-
(A) A more stable carbonium ion (B) A more stable carbanion
(C) A more stable free radical (D) None of these
93. Correct order of reactivity towards electrophilic addition reactions is:
(A) CH2  CH2  CH3  CH  CH2  (CH3 )2 C  CH2
(B) CH2  CH2  CH3  CH  CH2  (CH3 )2 C  CH2
(C) CH2  CH2  (CH3 )2 C  CH2  CH3  CH  CH2
(D) CH3  CH  CH2  CH2  CH2  (CH3 )2 C  CH2
94. Fastest rate of the electrophilic addition takes place in:

(A) (B)

(C) (D)

95. Consider the following reaction:

The major product obtained in the reaction is:

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

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 HBr
96.   Major Product:

(A) (B)

(C) both (A) and (B) in same amount (D) none of the above
97. Arrange the following reactions in decreasing order of electrophilic addition reaction:

(A) P > Q > R (B) Q > R > P (C) R > Q > P (D) P = Q = R
98. For the ionic reaction of hydrochloric acid with the following alkenes, predict the correct sequence of
reactivity as measured by reaction rates:
(I) ClCH=CH2 (II) (CH3)2.C=CH2 (III) OHC.CH=CH2 (IV) (NC)2C=C(CN)2
(A) IV > I > III > II (B) I > IV > II > III (C) III > II > IV > I (D) II > I > III > IV

H3C
99. CH2  HBr 
 A. (predominant), A is
CH3

Br Br
H3C CH Br
(A) H3C CH3
(B) CH 2 (C) H3C C CH2 CH3 (D)None of these.
CH3 CH3
CH3

HBr(1Mole)
100.  Major product:

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

101. Reaction of HBr with propene in the presence of peroxide gives -

(A) Isopropyl bromide (B) 3-bromo propane
(C) Allyl bromide (D) n-propyl bromide
102. 'The negative part of the added molecule goes to that carbon atom of unsymmetrical unsaturated
hydrocarbon which contain least number of H-atom" this statement is related to-
(A) Saytzeff's Rule (B) Peroxide effect (C) Markownikoff's rule (D) None of these

HBr
103. 
 Major Product:

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

HBr/CCl
4 
104.  Major Product:

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

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105. Consider the following rearrangement reaction:

Which of the following reaction co-ordinates best represents overall reaction?

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

106. Which of the following reagents will undergo Markovnikov addition, when reacted with HCl
(I) Propene (II) Nitroethene (III) Propenal (IV) Chloroethene
(A) I, II (B) II, III (C) III, IV (D) I, IV

107. CH2=CH–CH=CH2

At given temperature, these reaction tell about control of reaction which is:
(1) (2)
(A) Kinetic Thermodynamic
(B) Thermodynamic Kinetic
(C) Kinetic Kinetic
(D) Thermodynamic Thermodynamic
108. Anti–Markownikoff‘s addition of HBr is not observed in –
(A) Propene (B) But–2–ene (C) Butene (D) Pent–2–ene
CCl 3 Br
109. CH2=CH–CH=CH2   product. The major product is –
peroxide

(A) Br–CH2–CH=CH–CH2–CCl3 (B) CH 2  CH  CH  CH 2  CCl 3

|
Br
(C) CH2  CH  CH  CH 2  Br (D) None is correct
|
CCl 3
ADDITION OF X2
110. Which is expected to react most readily with bromine –
(A) CH3CH2CH3 (B) CH2=CH2 (C) CHCH (D) CH3–CH=CH2

111. ,A will have configuration

(A) (B) (C) both are (D) none is true


112. Butan-2-ol 
H /H2O

 
Br2 /CCl 4

Total possible products
(A)2 (B) 3 (C) 5 (D) 7

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113. CH2  CH  CH  CH2 
CCl Br
R O
 product. The major product is:
2
3
2

(A) Br  CH2  CH  CH  CH2  CCl 3 (B) CH2  CH  CH  CH2  CCl 3

|
Br
(C) CH2  CH  CH  CH2  Br (D) none is correct
|
CCl3
114. Ethylene reacts with Br2 to give 1, 2-dibromoethane. The anti-addition takes place due to the formation
of which intermediate?

(A) CH 2 Br  C H 2 (B) (C) BrCH  CH (D)

115. Plane polarized light is passed from the container after these reactions are completed. Select CORRECT
option
Br2 Br2
(P)  
CCl 4
 (Q)  
CCl 4


(A) No optical rotation is observed in container P as well as container Q

(B) Optical rotation is observed in container P only
(C) Optical rotation is observed in container Q only
(D) Optical rotation is observed in both the containers

Cl 2  H2 O
116.   Major Product

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

117. A reagent used to test unsaturation in alkene is -

(A) Ammonical Cu2 Cl 2 (B) Ammonical AgNO 3
(C) Solution of Br2 in CCl4 (D) Conc. H2SO4
118. The addition of bromine to 3-Methyl Cyclohexene in 1,2-dichloroethane produces ____ dibromo
derivatives:
(A) 2 (B) 3 (C) 4 (D) 6
119. The addition of Br2 to trans-2-butene produces
(A) (+) 2, 3-dibromobutane (B) (–) 2, 3-dibromobutane
(C) rac –2, 3-dibromobutane (D) meso-2, 3-dibromobutane

120. Cl 2

CCl 4


Stereochemistry of the product are:

(A) diastereomers (B) meso
(C) racemic mixture (D) pure enantiomers

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121. Which of the following is major product of reaction shown below?

Cl2

CH OH

3

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

122. Propene when heated with chlorine at about 500ºC forms -

(A) CH2Cl – CH = CH2 (B) CH3 – CHCl – CH2Cl
(C) CH2Cl–CHCl–CH2Cl (D) All of these

123. Which of the following reactions will result in the formation of a chiral centre in the product?
(A) CH3 CH  CH2  HBr   (B) CH2  CH2  HOBr  
(C) CH3CH2 CH  CH2  HBr 
H O
 2 2
(D) CH3 CH2 CH  CH2  HBr 


124. Which of the following reactions are correct?

peroxide
(I) CH3CH = CH2 + BrCCl 3 CH3—CH—CH2 CCl 3
Br
peroxide R—CHCH 2 CCl 3
(II) RCH = CH 2 + CCl 4
Cl
(A) I (B) II (C) both are correct (D) none is correct

ADDITION OF H2
125. The reaction CH2 = CH2 + H2 
 CH3 – CH3 is called -
Ni
250  300 ºC

(A) Wurtz reactions (B) Kolbe's reaction

(C) Sabatier-senderens reaction (D) Fittig reaction

126. Product of the reaction will be:

2 H /Ni


(A) racemic mixture (B) diastereomers (C) constitutional isomers (D) meso

2 H (1Mole)
127.  Product:

Pt

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

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128. If the following compound is treated with Pd/C in excess of H 2 gas, how many stereoisomers of the
product will be obtained?

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

ADDITION OF H2O (ACID CATALYSED, HYDROBORATION-OXIDATION,

OXYMERCURATION DEOXYMERCURATION)
129. Products of the reaction,
CH3


CH2  
D2 O / D
H3C

CH3
CH3 CH3 CH3

(A) H3C CH2D (B) H3C CH 2D

CH3 OD OD
CH3
CH3 H
H3C CH2
(C) H3C CH3 (D) CH3 D OD
OD D

(1)Hg(OAc)2 /H2 O/THF

130.   A. A is –
(2)NaBH 4 /NaOH/H2 O

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

131. Propene can be converted into 1-propanol by oxidation. Which set of the reagents is used to effect the
conversion?
(A) OsO4 – CHCl3 (B) O3/Zn – H2O
(C) Alkaline and cold KMnO4 (D) B2H6 and alc. H2O2.

(i ) B2 H6
132. 
(ii ) NaOH/H2 O 2
 Major Product is

(A) cis (B) trans

(C) Mixture of cis & trans in equal amount (D) Mixture of cis & trans in unequal amount

133. , A is:

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

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134. Which of the following is used for the conversion of 1-methylcyclo-pentene to
D

CH3
(A)BD3/THF followed by CH3COOH (B) BH3/THF followed by CH3COOD
(C)BD3/THF followed by CH3COOD (D) BH3/THF followed by CD3COOH

135. Arrange the given molecules in decreasing order of extent of hydration

I. cis CH3CH  CHCH3 II. trans CH3 CH  CHCH3
CH 3
III. trans CH= CHCH3 IV. C= CH 2

(A) IV > III > II > I (B) I > II > III > IV (C) I > II > IV > III (D) IV > III > I > II
dil.H SO
136. Ph – CH2   CH = CH2 
2 4
A , A is
(A) Ph—CH2 —CH2 —CH2 — OH (B) Ph  CH 2  CH  CH 3
|
OH
(C) Ph  CH  CH 2  CH 3 (D) Ph—CH2—OH
|
OH

137. B 
i) BH /THF
ii) H O /OH
3
  CH2 
H3O
 A , A and B are respectively
2 2

CH3 CH3
(A) CH2OH, CH2OH (B) ,
OH OH
CH3 CH3
(C) CH2OH , (D) , CH2OH
OH OH

CH3

138. In the following reactionH3C 
D2O/D
 A the product (A) is
CH3 CH2

CH3 CH3 CH3 CH3 H CH3

(A) H3C CH2D (B) H3C CH2D (C) H3C CH3 (D) H3C
CH3OD OD OD D CH3 D OD

139. Hydroboration oxidation and acid hydration will not give the same products in case of

(A) (B)

(C) CH2 = CH2 (D) CH3CH = CH —CH3

140. Which of the following reactions results in the formation of pair of diastereomers?
H 3C H H 3C H
(A) HBr (B) HBr
H3C H H 3C H
1. BH 3, THF
(C) HBr (D)
ROOR, UV 2. H2O, OH, H2 O
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 OH CH 2 Cl
141. + Br 
Br2CH 2 Cl 2 2

AA(minor)
(minor)
Minor product of the above reaction will be-
Br Br
OH Br OH OH
O
(A) Br (B) (C) (D)

OXIDATION OF ALKENES (OZONOLYSIS WITH KMnO4, OSO4, PERACID NAIO4 ETC)

142. Correct position of double bond in alkene is identified by -
(A) Hydrogenation (B) Ozonolysis (C) Baeyer's reagent (D) Dehydration

143. Ozonolysis of CH3–CH=C=CH2 will give

(A) Only CH3CHO (B) Only HCHO
(C) Only CO2 (D) Mixture of CH3CHO, HCHO & CO2
144. Ozonolysis of buta-1, 3-diene gives.
(A) HCHO and glyoxal (B) CH3CHO and glyoxal
(C) CO2 and glyoxal (D) HCHO, glyoxal and CH3CHO
145. The ozonolysis of 2, 4-dimethylpent –2-ene products
(A) two molecules of aldehydes
(B) two molecules of ketone
(C) one molecule of aldehyde and one molecule of ketone
(D) neither aldehyde nor ketone
146. Ozonolysis of m-xylene gives -
(A) Glyoxal
(B) Glyoxal + Methyl glyoxal
(C) Glyoxal+methyl glyoxal+dimethyl glyoxal
(D) Methyl glyoxal + dimethyl glyoxal
147. Ethylene reacts with osmium tetroxide to form an osmic ester which on hydrolysis gives:
(A) ethyl alcohol + osmic acid (B) glyoxal + osmic acid
(C) ethylene glycol + H2OsO4 (D) glycollic acid + H2OsO4

148. H2
1 eqiv.
O3 /H2 O
 A   B . A and B are:

(A) (B)

(C) (D) none is correct

149. Which compound will yield 5-keto-2-methyl hexanal upon treatment with O3 ?

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

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150. Give the reagent that would best accomplish the following reaction:


O
(A) Cold KMnO4 (B) CF3CO3H, H /H2 O (C) O 3 , Zn  H 2 O (D) KMnO 4 ,  , O H
CH2
|
dil. H 2 SO 4 conc. H 3 PO 4 (i ) O 2
151. CH 3  C  CH  CH 2    
 
(ii ) Zn/H 2 O
 ; final product is
|
CH3
O O
|| ||
(A) CH3  C  CH3 (B) HCHO  CH 3  C  CH  CH 3
|
CH3

(C) (D) CH3CHO + HCHO

152. The compound formed when 2-butene is treated with hot alkaline KMnO4 is:
(A) Acetaldehyde (B) Acetic acid (C) CH2 OHCH2 OH (D) CH3CH2 COCH3

153. Which alkene on oxidation with acidic KMnO4 gives only acetic acid?
(A) CH3  CH  CH3 (B) CH3  CH  CH  CH3 (C) ethylene (D) pentene – 2
154. Which of the following compound on oxidative ozonolysis give malonic acid as only product)
(A)CH2 = CH – CH2 – CH = CH2 (B) CH2 = CH – CH = CH2

(C) (D)

O3 /H2 O
155. Alkene A   + CH3COOH + CH 3  C  COOH , A can be –
||
O C(CH 3 ) 2
CHCH3
CH3 ||
(A) CH3-C-CH=C (B) CH 3  C  CH  HC  CH 3
CH3
(C) Both correct (D) None is correct

Excess CF3CO3H
156.  

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

OsO4
157. 
NaHCO3


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

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158. Which of the compounds with molecular formula C5H10 yields acetone on ozonolysis -
(A) 3-Methyl-1-butene (B) Cyclopentane
(C) 2-Methyl-1-butene (D) 2-Methyl-2-butene
159. Product formed by simplest alkene with Baeyer's reagent is -
CH 2  OH
CH 2  OH |
(A) CH3OH (B) CH3CH2OH (C) | (D) CH  OH
CH 2  OH |
CH 2  OH
160. Ozonolysis of benzene yields-
(A) Glyoxal (B) Glycerine (C) Glycol (D) Glycerol

161. . . The products are:

(A) (B)

(C) (D) none is correct

162. The olefin, which on ozonolysis gives CH3CH2 CHO and CH3CHO
(A) But-1-ene (B) But-2-ene (C) Pent-1-ene (D) Pent-2-ene.
163. A triene treated with ozone followed by CH3  S  CH3 to give following three products. What is the
structure of triene?

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

O /H O 
164. Point out (A) in the given reaction sequence: (A)   (B)   2CH3COOH  CO 2
3 2

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

165. The order of rate of halogenation and also ozonolysis of alkene is

(A) iii  ii  v  i  iv (B) iii  v  ii  i  iv

(C) iv  i  ii  v  iii (D) iv  i  v  ii  iii

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166. Dehydration of 2, 2, 3, 4, 4–pentamethyl–3–pentanol gave two alkenes A and B. The ozonolysis products
of A and B are –
O O
||
(A)A gives  CH3  3 C  C  C  CHand
3  3 HCHO
CH3  C  CH2  C(CH 3 )3 and HCHO
B gives
O O CH3
(B)A gives (CH3 )C  C  C(CH3 )3 and HCHO CH3  C  C  C(CH3B)3gives and HCHO
CH3
O O
(C) A gives (CH3 )C  C  CH(CH3 &
)2 HCHO (CH3 )  CH2  C B
 C(CH
gives 3&)3CH3CH2CHO
(D) None of these

reagent R 1
167. 
reagent R
 
2


R1 and R2 are –
(A) Cold alkaline KMnO4 , OsO4 /H2 O2 (B) Cold alkaline KMnO4 , HCO3H
(C) Cold alkaline KMnO4 , CH3  O  O  CH3 (D) C6 H5CO3H, HCO3H
H
CH3
168. H3C 
aq. alkaline KMnO 4

A
H
Which of the following is true about this reaction?
(A) A is meso-2, 3-butanediol formed by syn addition
(B) A ismeso-2, 3-butanediol formed by anti addition
(C) A is a racemic mixture of d and l-2, 3-butanediol formed by anti addition)
(D) A is a racemix mixture of d and l-2, 3-butanediol formed by syn addition

DIELS ALDER REACTION

CHCOOH
169. CH2=CH–CH=CH2 + || 

 product X by reaction R. X and R are
CHCOOH

(A) Diels Alder (B) (C) Diels Alder (D)

170. Which of the following hydrocarbon can react with maleic anhydride

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

PREPARATION OF ALKYNES
171. When CH3CH2CHCl2 is treated with NaNH2 the product formed is -
(A) CH3 – CH = CH2 (B) CH3 – C  CH
(C) CH3CH2CH(NH2)2 (D) CH3CH2CHCl(NH2)
172. Alkanide formed when dry ammonia and sodamide heated with of the following-
(A) CH2 = CH2 (B) C6H6 (C) CH3–CCH (D) CH3–CC–CH3

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173. CH3CH2Br reacts with sodium acetylide to form -
(A) 1–Butyne (B) 1–Butene (C) 2–Butene (D) 2–Butyne
174. Chloroform, on warming with Ag powder, gives -
(A) C2H2 (B) C2H4 (C) C2H6 (D) C6H6
175. When CH3CH2CHCl2 is treated with NaNH2 the product formed is -
(A) CH3 – CH = CH2 (B) CH3CH2CHCl(NH2) (C) CH3CH2CH(NH2)2 (D) CH3 – C  CH
176. End product of the following sequence is:
2
H2 O Hg
CaO  C 
Heat
 (A)   (C) 
H2 SO 4
(C)
(A)Ethanol (B) Ethyl hydrogen sulphate
(C)Ethanal (D) Ethylene glycol.
177. Acetylene can be prepared from -
(A) Potassium fumarate (B) Calcium carbide
(C) Ethylene bromide (D) All of the above

PROPERTIES
ACIDITY OF ALKYNE
178. But-1-ene and propyne are distinguished by-
(A) Baeyer's reagent (B) Hinsberg's reagent (C) Tollen's reagent (D) None
179. With sodium, liberation of hydrogen gas is possible with the following hydrocarbon -
(A) CH4 (B) C2H6 (C) C2H4 (D) C2H2
180. Ammonical solution of cuprous chloride give red precipitate with -
(A) H–CC–CH3 (B) CH2=CH2 (C) (C2H5)2C=CH2 (D) CH3–CC–C2H5
181. Acetylene gives -
(A) White precipitate with ammonical AgNO3& red precipitate with ammonical Cu2Cl2
(B) White precipitate with both ammonical AgNO3& Cu2Cl2
(C) Red precipitate with both ammonical AgNO3& Cu2Cl2
(D) Red precipitate with AgNO3& White precipitate with Cu2Cl2
182. In which of the following hydrocarbons, hydrogen is most acidic -
(A) C6H6 (B) CH2 = CH2 (C) CH  CH (D) CH3 – CH3
183. In CHCH, hydrogen atom will be–
(A) Acidic (B) Basic (C) Neutral (D) None
184. CH3CH2Br reacts with sodium acetylide to form -
(A) 1–Butyne (B) 1–Butene (C) 2–Butene (D) 2–Butyne
185. Chloroform, on warming with Ag powder, gives -
(A) C2H2 (B) C2H4 (C) C2H6 (D) C6H6

ADDITION REACTION OF ALKYNES& REDUCTION

186. Which one of following react with HOCl to form
CH3 – CO – CHCl2 product -
(A) CH3–CC–CH3 (B) CH3–CCH
(C) CHCH (D) CH3–CH2–CCH

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187. Which one is the false in the following statements -
(A) Each carbon in ethylene is in sp2 hybridisation
(B) Each carbon in acetylene is in sp3 hybridisation
(C) Each carbon in benzene is in sp2 hybridisation
(D) Each carbon in ethane is in sp3 hybridisation
188. HC  CH 
HOCl

(excess)
A
CH 3  C  CH 
HOCl

(excess)
B
A & B are respectively
(A) Cl 2 CH  CHO and CH3  CCl 2  CHO (B) Cl 2 CH  CHO and CH3 C  CHCl 2
||
O
(C) Cl 2 CH  CHO and CH3CCl 2 COOH (D) Cl 2 CHCOOH and CH3 C  CHCl 2
||
O
189. Alkynes mainly shows -
(A) Polymerisation (B) Electrophilic addition
(C) Free radical substitution (D) All of the above
190. Tollen's reagent is -
(A) Solution of CuSO4 (B) Ammonical AgNO3 solution
(C) Anhydrous ZnCl2 (D) Fuccine
191. Cylindrical shape of alkyne is due to-
(A) Three C – C sigma bond (B) Three C – C pi bond
(C) Two C – C sigma one C – C pi bond (D) One C – C sigma and two C – C pi bond
192. Which hydrocarbon reacts with sodium and liquid NH3-
(A) CH3–CH2–CH2–CH3 (B) CH3–CC–CH3
(C) CH3–CH=CH–CH3 (D) CH3–CH2–CH=CH2
2 
Hg /H /H2 O
193. H3 C  C  C  OCH3  Product. Major product of the reaction will be
(A) H3 C  C  CH2  OCH3 (B) H3 C  C  C  OCH3
|| || ||
O O O
(C) H3 C  CH2  C  OCH3 (D) H 3 C  CH 2  CH 2  OCH 3
|| |
O OH
Na/NH3
194. B 
Lindlar
R–CC–R  A
A and B are geometrical isomers (R–CH=CH–R) –
(A) A is trans, B is cis (B) A and B both are cis
(C) A and B both are trans (D) A is cis, B is trans
195. 2-Butyne which treated with lithium in presence of liquid ammonia gives
(A) cis-2-butene (B) trans-2-butene (C) n-butane (D) 1-butyne
196. Which reagent will be used for the given conversion?

(A) Na /Liq. NH3 (B) H2 , Pd  CaCO 3 (C) Li, Ph  NH2 (D) H 2 ,Pt
197. In the following sequence of reactions, identify the product (D).
alk. KOH NaNH
CH  CH  HBr
 (A) 
HBr
 (B)   (C)  (D) 2

(A) Ethanol (B) Ethyne (C) Ethanal (D) Ethene

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198. Which one of following react with HOCl to formCH3 – CO – CHCl2 product -
(A) CH3–CC–CH3 (B) CH3–CCH (C) CHCH (D)CH3–CH2–CCH
H , Pd  CaCO
199. Ph  CH  CH  Ph 
Cl
CCl
2NaNH
 X  2
 Y  2
Z 2 3
4

Identify product (Z) of the reaction:

(A) (B) (C) (D) Ph  C  C  Ph

200. An organic hydrocarbon on oxidative ozonolysis produces oxalic acid and butanedioic acid. Its structure
is

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

201. An unknown compound A has a molecular formula C4H6. When A is treated with excess of Br2 a new
substance B with formula C4H6Br4 is formed. A forms a white ppt. with ammonical silver nitrate
solution. A may be -
(A) But-1-yne (B) But-2-yne (C) But-1-ene (D) But-2-ene
202. Which molecule will give following dicarboxylic acid upon treatment with acidic solution of KMnO4 ?

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

2 4  X dil. H SO
203. What is X in following reaction HCCH 
HgSO4
(A) CH3COOH (B) CHO – CHO
(C) CH3CHO (D) CH2OH – CH2OH
204. In the reaction CH3 – C  CH + H2O 
2 
Hg ,H O
 X, the product X is -
 3

(A) CH3CH2CHO (B) CH3COCH3 (C) CH3COOH (D) CH3COCH2CH3

205. Which of the following reagents would best accomplish the following transformations?

(A) Excess B2 H6 ; NaOH /H 2 O 2 followed by OsO 4

(B) Excess Hg(OAc)2 /H2 O; NaBH 4 , followed by conc. H2 SO 4 , 

O
(C) O 3 , Zn /H 2 O followed by Hg(OAc)2 /H2 O; NaBH4 , OH
(D) OsO 4 ; NaHSO 3 followed by NaOH

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206. How is the following transformation best carried out?

(A) OsO 4 ; NaHSO 3 (B) H2 SO4 /H2 O (C) HgSO 4 /H2 SO 4 (D) HIO4

BH3 THF
207. B  
CH3–CCH 
HgSO /H SO
 A, A and B are –
4 2 4

H2 O2 , OH

O O
|| ||
(A) CH3 CH2 CHO, CH3  C  CH3 (B) CH3  C  CH3 CH3 CH2 CHO

(C) CH3CH2CHO (both) (D) CH 3  C  CH 3 (both)

||
O
208. The compound which gives only acetaldehyde on ozonolysis is -
(A) 1-Butene (B) 2-Butene (C) Ethene (D) Propene
209. The compound formed by ethyne and HBr will be -
(A) Ethylene bromide (B) Bromoethane (C) Ethylidene bromide (D) Vinyl bromide
210. Shortest C – C bond length will be present in -
(A) Benzene (B) Ethene (C) Diamond (D) Acetylene
211. Lindlar‘s catalyst is
(A) Pt in ethanol (B) Ni in ethanol
(C) Pd with BaSO4 (D) Na in liquid NH3

212. Which of the following is true?

(A) Acetylene is more reactive than ethylene to an eectrophilic attack
(B) Acetylene is less reactive than ethylene to an electrophilic attack
(C) Acetylene may show more reactivity or less reactivity towards electrophilic attack depending upon
electrophilic reagent
(D) Acetylene and ethylene show identical reactivities towards an electrophilic attack

BENZENE & ELECTROPHILLIC AROMATIC SUBSTITUTION REACTION (PART-1)

213. Benzene is extraordinarily stable because -
(A) It is a liquid
(B) It has a cyclic
(C) It has a planar & cyclic structure and has six  electrons
(D) It has three double bonds
214. Which one of the following statements is wrong-
(A) Aromatic compounds are generally unstable.
(B) Aromatic compounds are richer in carbon content.
(C) Aromatic compounds show substitution reactions.
(D) Aromatic compounds burn with smoky flame.
215. Which of the following aromatic compounds is more reactive towards electrophilic substitution-
(A) Benzene (B) Benzaldehyde (C) Benzonitrile (D) Toluene
216. Nitration of benzene takes place by following reagent–
(A) conc. H2SO4 (B) conc. H2SO4 + conc. HNO3
(C) H2SO5 (D) None of these

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217. Acetylation of benzene takes place by –
(A) CH3COCl+AlCl3 (B) CH3Cl + AlCl3 (C) Cl2 + h (D) None of these
218. Benzene reacts with fuming sulphuric acid to give-
(A) Sodium benzene sulphonate (B) Benzene sulphonic acid
(C) Sodium benzoate (D) All the above
219. Benzene on treatment with propyl chloride in presence of anhydrous AlCl3 gives mainly -
(A) toluene (B) ethylbenzene
(C) propylbenzene (D) isopropylbenzene
220. When benzene is heated with acetic anhydride in the presence of anhydrous aluminium chloride at
80°C, the product formed is-
(A) Benzoic acid (B) Benzophenone
(C) Acetophenone (D) Ethyl phenyl ketone
221. Which of the following compounds undergoes nitration with greatest difficulty -
(A) Benzene (B) Toluene
(C) Nitrobenzene (D) m-Dinitrobenzene
222. Benzene undergoes -
(A) Nucleophilic substitutions (B) Electrophilic substitutions
(C) Electrophilic additions (D) Nucleophilic addition
223. Benzene is obtained when phenol is distilled with-
(A) Copper turnings (B) Alumunium dust (C) Zinc dust (D) Ni
224. Which of the following reactions of benzene does not prove the presence of three carbon-carbon double
bonds in it-
(A) Fromation of a triozonide
(B) Hydrogenation of benzene to cyclohexane
(C) Fromation of C6H6Cl6 by addition of chlorine
(D) Formation of nitrobenzene on heating benzene with a mixture of concentrated nitric acid and
sulphuric acid
225. Which of the following statements is correct -
(A) Bromination of toluene occurs faster than that of benzene
(B) Nitration of toluene is difficult than that of nitrobenzene
(C) Bromonium ion Br+ is good nucleophile
(D) Sulphonation of benzene is irreversible
226. Benzene reacts with trichloromethane in the presence of anhydrous AlCl3 to give -
(A) diphenyl (B) diphenylmethane
(C) triphenylmethane (D) triphenylchloromethane
227. Nitration of nitrobenzene is difficult than that of toluene. This is because
(A) Nitro group is an electron donor
(B) Nitro group withdrawn electrons from the ring and thus deactivates the benzene ring
(C) Methyl group is an electron attracting group
(D) Methyl cation attracting electrons
228. Among the following compounds (I-III), the correct order in reaction with electrophile is
OCH3 NO2

(I) (II) (III)

(A) I>II>III (B) III<I<II (C) II>III>I (D) I=II>III

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229. Which of these give three isomeric products when one more substituent is introduced through an
electrophilic substation
Br Br Br

Br Br
(A) (B) (C) (D)
Br Br
Br
230. Arrange given a,b,c in decreasing order of reactivity towards Electrophilic aromatic substitution
Reaction
CH3 CD3 CT3

(a) (b) (c)

(A) a>b>c (B) c>b>a (C) a>c> b (D) c>a>b
231. Major product formation takes place at which position in ArSE Reaction
2 3 4 5

1 O CH 2 6

(A) 3 (B) 1 (C) 6 (D) 4

232. Which of the following correctly represent the major product of electrophilic aromatic substitution
O
(A) (B) OCH3 (C) C–CH3 (D)

233. Electrophilic aromatic substitution reaction most likely to take place at

1
4
2
(I) 3
(II) .. 5
N
.. N
H
(A)2 and 4 (B) 2 and 5 (C) 3 and 5 (D) 1 or 3 and 4.
234. The relative rates of mononitration of R – C6H5, where R = CH3, – NO2, – OH, – Cl are :
(A) CH3> OH > NO2> Cl (B) OH > Cl > CH3> NO2
(C) OH > CH3> NO2> Cl (D) OH > CH3> Cl > NO2
235. Rank the following compounds in order of decreasing reactivity towards electrophilic substitution
reaction.
(I) Chlorobenzene (II) 4-nitrochlorobenzene
(III) 2, 4-dinitrochlorobenzene (IV) 2, 4, 6-trinitrochlorobenzene
(A) I>II>III>IV (B) I>III>II>IV (C) III>I>IV>II (D) IV >III>II>I
236. In the compound C6H5Z which of the following is predominatly ortho/para directing?
(A) Z = – NO2, — Cl, — OH (B) Z = – OMe, — CN, — NH2
(C) Z = – NHCOCH3, — Cl, — COOH (D) Z = – NHCOCH3, — CH3, — Br
237. Order of rate of electrophilic substitution reaction is:

(A) Q > P > S > R (B) Q > P > R > S (C) P > Q > S > R (D) P > Q > R > S

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 
NO 2 (Mononitration )
238.  

The nitration will mainly take place at position :

(A) 1 (B) 2 (C) 3 (D) 4
239. Benzene + CH3Cl 
A
 Toluene. [A] is-
(A) Ni (B) Anhydrous AlCl3 (C) Pd (D) Pt
AlCl
240. Benzene + C2H5Cl [X]   ,[X] is 3

CH CH2 CH3 CH2 CH3

(A) C6H5CH3 (B) (C) (D)
CH3
CH3
Me3C–CI Ph–COCI
241. Br2 / AICI3
Product is
AICI3 AICI3

O O O OO Me O O O Me O Me O
Me O Me Me O Me Me O
Me MeMe Me O
MeMe
Me O Me O
CC–Ph –Ph C –Ph C –Ph
C –Ph C –Ph Br Br –Ph C –PhC –Ph
Br –Ph
C –CPh C –Ph Br
Br C –Ph
C –C
Ph
C –Ph Br C –Ph
(A)
(A) (A) (A) (B)
(B) (B)
(A)
(B) (C)
(C) (B) (C) (D) Br
(C) (D)
Br (C)
(D)
Br (D) (D)
Br
Br C(Me)3C(Me)3 C(Me)3
C(Me)3C(Me)3 BrC(Me)Br3
C(Me)3 Br C(Me)3

BENZENE & ELECTROPHILLIC AROMATIC SUBSTITUTION REACTION (PART-2)

242. The major product of reaction
O
C O

HNO3 + H2SO4

OMe
O O O O O
O OO O O O O O OO O
CO OC O C O C OO C C OO C
O C CO O C O
C CC C OO O C CO
NO2 NO2 NO2
NO 2
(A) (A) (A)
(A) (B) (B)
(A) (B) (B) (B)(C)(C) (C)
(C) (D)
(C) (D) (D) (D)
(D)
NO2
NO2 NO2 NO2 NO2
NO2
NO2 NO2
OMe OMe NOOMe NO
2 OMe 2 OMe NO2 OMe OMe OMe OMe
OMeOMe OMe OMe
OMe NO2 OMe OMe

CH3 CH2 CH2 Cl

243. 
AlCl
Major product ―X‖
3


CH3 CH2 COCl N 2 H 4 /OH /

AlCl
 A  Y
3

I. X is ‗n-propyl benzene‘ II. X is Isopropyl benzene

III. Y is Isopropyl benzene IV. Y is n-propyl benzene
Correct Options for X and Y
(A)I & II (B) II & IV (C) III & II (D) I & IV

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 O
O  C  CH3
2 Br  FeBr
3  X, ―X‖ can be
244. 
OC Br
OCH3
Br O O
O  C  CH3 O  C  CH3
(A) (B)
OC Br OC
OCH3 OCH3 Br
O
Br
Br O  C  CH3
(C) (D) HO
OC
OCH3 Br

245. A + Cl2 

110
 , [A]
CCl 3
is –

(A) Toluene (B) Chloro Benzene (C) Phenol (D) Nitro Benzene

246. Which of the following structures correspond to the product expected, when excess of C6H6 reacts with
CH2Cl2 in presence of anhydrous AlCl3

(A) CH (B) CHCl2

Cl
Cl
(C) C (D) CH2
Cl
247. The number of benzylic hydrogens in ethylbenzene is-
(A) 3 (B) 5 (C) 2 (D) 7
248. Which of the following is best sequence of reagents for the conversion of
CH 3



Br

Br2 /Fe conc.H2 SO 4
CH3 Cl/AlCl 3 H3 O
(A)  
   
 


CH 3 Cl/AlCl 3 conc. H 2 SO 4 Br2 /Fe H2 O
(B)       

CH3Cl/AlCl 3 3Cl 2 /h Br2 /Fe
(C)       
Zn/HCl

HNO  conc. H SO CH Cl/AlCl NaNO /HCl
(D)  3
 
2 4
 
3Sn/HCl
 
3
 
CuBr
2

249. Which of the following is not the correct route to prepare compound ‗X‘ ?
NO2
X =X —C—
O
NO2
HNO3  H2 SO4
(A) C—Cl + AlCl3 + 
 (B) —C—  
O O
NO2
 
CrO 3 /P iridine NO 2 BF4
(C) + Cl—C— 
AlCl3
 (D) —CH—  (1)
 
(2)

O OH
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250. The product of the following reaction is
AcCl/AlCl 3 AcCl/AlCl 3 Br2 /Fe
     

Br Br
(A) C–CH3 (B) C–CH3
O O
H3C–C H3C–C
O O
O
H3C–C Br
(C) H3C–C C–CH3 (D)
O O
Br C–CH3
O
251. Attacking or reactive or electrophilic species in nitration of benzene is or In the nitration of benzene with
concentrated HNO3 and H2SO4 , the attack on ring is made by :
(A) NO 2 (B) NO 2 (C) NO 3 (D) NO2
252. Electrophile in the case of chlorination of benzene in the presence of FeCl3 :
(A) Cl+ (B) Cl– (C) Cl (D) FeCl3
253. The given product can‘t be formed by which set of reactants in the presence of AlCl3 catalyst ?

(A) + (B)

(C) (D) All of these

254. In the reaction for dinitration

The major dinitrated product X is

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

255. Most common reactions of benzene (aromatic hydrocarbon) and its derivatives are :
(A) Electrophilic addition reactions (B) Electrophilic substitution reactions
(C) nucleophilic addition reactions (D) Nucleophilic substitution reactions

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 Br / CCl
256. 
2 4
 The product is :

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

257. The product of the following reactions is

O O OOO OO
O O O || || || ||
|| || || || ||
||
CH – CCH– –CH
3CI C 3– –CIC – CI CH CH
3 3––CC––CI CI
CHC CCH33 CH3
C CC CH CH
33
3
AICI3 AICI3 AICI3 AICI
AICI 33

O O O O O O O O OO
|| || || || || || || || || ||
(A) (A)
(A)
(A) C – CH3C –CCH
(A)
(A) – 3CH 3
C C
(B)
– –
CHCH (B)
3 3 (B) C – CH3 C(B)
– CH
(B)
(B) 3 C – CH 3
C C––CH
CH
33

C=O C=CO= O CC==OO C – CHC – CH3C – CH3 CC––CH

CH 33
3
CHCH CHCH O O O OO
CH 3 3 3 33

O O O OO O O O OOO O OO
|| || || || ||O || || || || ||
(C)
(C)
(C) CHC
–(C)
C(C) – CH
C – CH (D) H CC C–H
(D)
–
–CH
C
CH
C –
(D)
3 3 C
H C – C (D)
C H
(D)–
(D) HC
CH
3 3C–
C –C
–CCH3 C – CH CC––CH CH
33
(C) 3 3 3 3 3 3 3 3

H3C – CHH
3C3C
–C–C HH3C––CC
3C

O OO OO
258. Which of the following is correct with respect to major product formed
Isobutylchloride
(A) Benzene   AlCl 3
  Isobutyle Benzene
Methyl chloride
(B) Aniline 
 AlCl 3
Orthotoluidine
ICl+AlCl3
(C) Benzene   Chlorobenzene
H S O
(D) Benzene 
(Oleum)
 Benzene Sulphonic Acid
2 2 7

259. Which of the following is best sequence of reagents for the conversion of
CH3

Br

Br2 /Fe conc. H 2 SO 4
H3 O CH3 Cl/AlCl 3

(A) Br / Fe 
conc. H 
SO
CH 
CI 
/ AICI  H3O
2 2 4 3 3
(A) CH3 Cl/AlCl 3 conc. H 2 SO 4 Br2 /Fe H3 O
(B) 
 
   A
CH
CH3CI / AICI /h
3Cl 2conc. H3O
(C) 
(B) 3
Cl/AlCl 3
3  H2SO
Br2 /Fe
 Br2 / Fe
4  
Zn/HCl

HNO3  conc. H2 SO 4 CH3 Cl/AlCl 3 NaNO2 /HCl

(D) CH  3CI
  Br
 
Sn/HCl
 
Zn / HCI 
CuBr

3CI / AICI3 2/ h 2 / Fe
(C)
HNO3 + conc. H2SO4 CH3CI / AICI3 Sn / HCI NaNO2 / HCI CuBr
(D)

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SINGLE CORRECT QUESTIONS

1. Br2 , hv
  Product:

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

2. The correct statement about the following reaction is :

CH2 – CH3
| Cl2 h
C – CH2 – CH3+ (excess) + C–O–O–C
| || ||
H (II ) O O
(excess)
(III)
(I)
(A) By absorption of one mole of photon of light only one mole of product (racemic mixture) is obtained
(B) In total 6 optically active isomers are obtained on monochlorination of side chain
(C) Homolysis of III takes place in chain propagation step
(D) Homolysis of II takes place in the slowest step.
 Cl2 , heat or
3. CH3  CH2  CH  CH3   Products
| light
Cl
Sec  butylchloride
Which statement is incorrect ?
(A) One of the product exist as three stereoisomers
(B) Two pair of diastereomers are obtained only
(C) Only one meso stereoisomer is obtained
(D) Two pair of enantiomers are obtained
4. The addition of HI in the presence of peroxide does not follow anti-Markovnikov‘s rule because
(A) HI bond is too strong to be broken homolytically
(B) I atom is not reactive enough to add on a double bond
(C) I combines with H to give back HI
(D) HI is a reducing agent
5. A & B products respectively are

(A) (B)

(C) (D)

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 Mg
6. 
NBS
 X 
HBr
H2 O2 , 
 Y 

Z; Z, is:

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

7. Give the major product of following reaction:

Br2 /CCl 4
  Major Product:

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

X
Br2
8.   (stereoisomer) , X may be:
CCl 4
()

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

COOH
HOOC
9. BD3 -THF H2O2 ,OD -
C=C   
D2O
 Product
H H
COOD COOH COOH
COOH
H
H D H D H D
D (B) (C) (D)
(A)
OD H OD H OH DO H
H
COOH COOD COOH COOH

10. , The probable structure of ‗X‘ is

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

Na, Liq. NH3

11.   Major project:

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

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12. Hydrocarbon 'A' of molecular formula C5H8 gives white precipitate with ammonical AgNO3 solution.
'A' on treatment with acidified K2Cr2O7 produces acid of the formula (CH3)2 CHCOOH. Hence the
compound 'A' is-
(A) (CH3)2CH – CH = CH2 (B) CH3 – CH = CH – CH = CH2
(C) (CH3)2CH – C  CH (D) CH3CH2CH2 – C  CH

13. Which statement is correct about photochemical bromination of Butane ?

Br2 , h
CH3 – CH2 – CH2 – CH3 
(A) 1-Bromobutane and 2-Bromobutanes are formed in equal amounts.
(B) 2-Bromobutane is formed with faster rate than 2-chlorobutane in the other experiment of
chlorination.
(C) The major product is an equimolar mixture of two compounds
(D) Homolysis of C – H bond has lower activation energy than homolysis of Br – Br bond.

Cl
AlCl 3 Zn/Hg
14.   A 
conc.HCl
B AlCl3
C
Cl O

The product C is

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

O

H SO Zn,Hg,HCl NBS
15. COOH 2 4  A 
 B   C (Major product );
Δ hν
CH3
Major product (C) is
CH3 CH3 Br CH3 Br CH3

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

O
Br

16. The end product of following sequence of reactions is

CH3
Cl2 ,h
(1)
 
PhH, AlCl3
(2)


(A) (B) CH2

(C) CH3 (D) CH3 CH3

17. Select the reactions in which the correct orientations have been mentioned in the major products.
CH3 CH3 CH3

NO2
HNO  H SO
(A) 
3 2 4
>
NO2
Cl Cl Cl

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 CH3 CH3 CH3
Br
Br /FeBr
(B) 
2 3
>
Br

NHCOCH3 NHCOCH3 NHCOCH3

CHO CHO CHO

Br /FeBr Br
(C) 
2 3
 >
OH OH Br OH

(D) CH2 

Mononitration
 O2N > CH2 CH2 NO2

NO2 NO2 NO2

Br2 /Fe
18.  
(1 eq.)

(A) (B)

(C) (D)

19. Cl 2 , CCl 4
 

(A) (B) (C) Ph  C  C  CH3 (D)

H+
20. O

Major product of the reaction is-

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

OH
21. Which reaction shows the correct stereochemical structure of product?
Br Br Br Br
CH3 Br2
H Br2
(A) 
C=C H C—C H (B)  H H
H CH3 CH3 CH3
Br
| H Cl
NOCl
Br2
(C) CH 3  CH  CH 2 
H2 O
 CH 3  CH  CH 2 (D) CH3–CH=CHD  H3C C—C D
| ON H
OH

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22. Which of the following reactions results in the formation of a pair of diastereomers?

(A) 
HBr
 (B) 
HBr


BH3 .THF
(C)  HBr
H 2 O 2 , hv
 (D) 
H O /OOH

2 2

23. Give number of the products including stereoisomers formed in the following reaction.

CH2 
 NBS
h

(A) 5 (B) 6 (C) 7 (D) 4


H (i) t-BuOK / (i) (CF 3COO) 2Hg / H 2O
24. (A) - ,A and(B)
B respectively are
(ii) D 2/Ni (1eq) (ii) NaBH 4, OH
Br

O 2N 18
OH H
(A) O2N C C ; O 2N C C

D D D D
18
H HO

(B) O2N C C ; O 2N C C

D D D D
18
H HO

(C) O2N C C ; O 2N C C

D D D D
18
H HO

(D) O2N C C ; O 2N C C

D D D D
25. The most stable conformation of the product of following reaction
HBr / R2O2 HBr / dark
C CH (1 eqivalent)
HH H H Ph
Ph Ph Ph Ph
Ph Ph Ph HH H H
Ph Ph PhBr
Ph Br Br Br HH H HBr Br Br Br HH H HBrBr Br Br BrBr Br BrHH H H
(A)
(A) (A) (A) (B)
(B) (B) (B) (C)
(C) (C) (C) (D)
(D) (D) (D)
HH H H HH H H HH H H HH H H HH H H BrBr Br Br Ph Ph Ph PhBrBr Br Br
Br
Br Br Br BrBr Br Br Br
Br Br Br HH H H
conc. H2 SO 4
26. CH3  CH  CH2  CH3   Pr oduct (I)  Pr oduct(II)
|
OH
What is not true regarding the products:
(A)product – I and II are position isomers
(B) Product – I and II contains the same number of sp3 and sp2 carbon atoms
(C)the yield of the product I and II is same
(D)reaction obeys Saytzeff rule

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27. Product of the reaction will be:
H2 /Ni
 

(A) racemic mixture (B) constitutional isomers (C) meso (D) diastereomers

28. What reagent is needed to accomplish the following synthesis?

(A) H3 O (B) KMnO4 , OH (C) O 3 , Zn /H 2 O (D) Ph  CO3H

29. Which of the following, when undergoing addition of HBr, will form only a pair of diastereomers?
Cl H HO H H3C CH3
(A) (B) (C) (D)

30. The major product of the following reaction would be

Br
NH BrBr
Br
NH
NHNH N
N N NN N
N NN N NN
(A)
(A)
(A) (A) (B)(B) (B)
(B) (C)(C) (C)
(C) (D)
(D) (D)
(D)
(A) Br (B) (C) (D)
BrBrBr Br Br
Br H H
BrBr H HH BrBrBr H HH BrBrBr
Br
31. In the following series of reactions, the major products P and S are respectively.
Br2 / h tBuO , (i) HOBr/H+ (i) HOBr/H+
(P) (Q) (R) (S)
(ii) ThO2, (ii) ThO2,
(iii) alc.KOH, (iii) alc.KOH,
(A) (A) ; ; (B) (B) ; ;
(A) Br (A) ; (B)
Br (B)
(A) ;Br (B) ; ;
Br
Br Br Br
Br

(C)
(C) (C) ; ; (D) (D)
(D) Br ; Br ;
(C) ; (D) (D) Br ;
(C) Br ; Br Br ;
Br Br
32. The end product 'W' in the following sequence of reactions is :
CH
CH22CH
CH3CH alc. KOH
3 CH3 alc. KOHalc.
Y YKOH
CH2CH3 2 NBS alc. KOH Y 2
Hg(OAc)
NBS (X)
NBS Y Hg(OAc)
Hg(OAc)
2W
(X) (X) NaBH
Hg(OAc) W 2 W
NBS aq.
aq.KOHKOH NaBH4 2NaBH
(X) Z
aq. KOH 4 W4
aq. KOH Z NaBH4
Z
CH Z CHCH CHCH
CH3
3 CH3
3
3
3
CH3 3 CH3
(A) Ph – CH2 – CH2 – O – CH –3 Ph CH CH
(B) Ph– CH – O CH
3 – CH – Ph 3
(A) Ph – CH
(A) 2 –– CH
Ph CH22 –– OCH – CH – Ph (B) Ph–(B CH – OCH
) Ph– – CH– O– –PhCH – Ph
2 – O – CH – Ph
(A) Ph – CH2 – CH2 – O – CH – Ph (B) Ph–CHCH – O – CH – Ph
= CH
CH = CH 2
CH 2 = CH2
CH = CH2
(C) Ph – CH2 – O – CH2 – CH2 – Ph (D)
(C) Ph –
(CCH 2 –– O
) Ph – CH
CH 2 –– CH
CH22 –– Ph (D)
2 –O CH2 – Ph (D)
(C) Ph – CH2 – O – CH2 – CH2 – Ph (D)
Ph – CH – CH3
Ph – CH Ph– –CHCH3 – CH3
+ Ph – CH – CH3
33. Ph–C C–Ph Na/NH Na/NH3
Na/NH A 3 HOCl/H +
B ;+ B is
Ph–C C–Ph
Ph–C C–PhNa/NH3 3 AHOCl/H
A HOCl/H +HOCl/H
B ; BBis; B is
Ph–C C–Ph Ph A B ; B is
Ph Ph Ph Ph
H Ph OH Ph Ph Ph Ph
Ph Ph
(A) H H H OHOH OH (B) HO HO HO
H
H H (C) H H H OH OH OH (D) B and C both
(A) (A) (B) Cl (B) (C)
HH (C) (D) B(D)
and C both
B and C both
(A) ClCl Cl H H H (B) HO Cl Cl
HH
H H (C) H H
OH
Cl
Cl Cl (D) B and C(D) B and C both
both
Cl Ph H Cl Ph H H Ph Cl
Ph Ph Ph Ph Ph Ph
Ph Ph Ph

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 34. Consider the following reactions
H5C2 C2H5
C=C
H H
R1 R H C2H5
2 C=C
H5C2 H
H5C2—C C—C2H5 R3
H5C2 C CH2 C2H5
R4
O
2CH3 CH2 COOH
The correct set of reagents for these reactions is
R1 R2 R3 R4
(A) H2/Lindlar catalyst Na / Iiq.NH3 (i) O3, (ii) H2O H2O,H2SO4,HgSO4
(B) H2/Lindlar catalyst Na / liq.NH3 H2O,H2SO4,HgSO4 (I) O3, (ii) H2O
(C) (i) O3, (ii) H2O H2O,H2SO4,HgSO4 Na / Iiq.NH3 H2/Lindlar catalyst
(D) H2O,H2SO4,HgSO4 H2/Lindlar catalyst (i) O3, (ii) H2O Na / Iiq.NH3
35. The major product of the following reaction is :
–
Na // ether
ether Br2Na
Na / etherBr / h Br / hC
2 / h / ether
C2H
H5OO– ether
// C
C –
HhO5OH,
OH, – –
Br Cl
Na 2 5 / Br
2 Na C 22H2/H
2 Br
5 5 / C2HC 2H/5O
OH,
52 h / C2HC5OH,
2H5O / C2H5OH,
Br Br Br Cl Br
Cl(1) Cl Cl
(2) (1) (2) (3)
(1) (1) (2) (1) (3)(2) (3) (2) (3) (3)

(A)
(A) (A) (B)
(A) (B) (B)
(A) (C)
(B) (C) (C)
(B) (D)
(C)(D) (D)(C) (D) (D)
Me Me Me Me
D Et
36. The most appropriate major product of theEtfollowing sequence of reactions
D wouldEt be. DH Et DH
(A) (A)(±) (±) (B) (B)(±)
O H OH H OH D H D H
CH3CH2 CH3 
CC CH3  C  O  O  H LiAlD4   H O
3 Me 
H   
Me CH3 CH3
H3C
Me Me Me Me
Me Me CH3 CH3
Et D
Et D Et DH
Et
Et OH Et
DH OH CH3CH2 CH
DH3CH2
A) (A) OH (±) (±) (B) (C)H (±)
(B) (±)
(C)
H D (±) (±) (D) (D)
H OH DH HD H D H OD H
Me Me CH3 CH
Me3 Me CH3 CH3

DMe D(1) C H CO H (2) CH CH

MgBr (3)H O/H 

C  C  
Me
37. 6 3  
5 3 CH3  Product; Product is:
3 2

CH3 H
Et Et C
OH OH
CH3CH2 DH
CH3CH2 DH
C) CH3 (±)
(C) (±) (D) (D)
H DH CH3 D
H OD
H OD
Me OH OH CH3CH OH3 CH3 OH CH3 CH3CH3
Me
(A) D  C  C  H (B) DCCH (C) D  C  C  H (D) D  C  C  H
(CH3 )3C D (CH3 )3C D (CH3 )3C D (CH3 )3C D
38. The final product of the following reaction is
Ph
H o–COCH3
BrCl/CCl4
H Me
Ph
Ph Ph Ph PhPh Ph Ph PhPh Ph Ph Ph Ph Ph Ph Ph
H H Cl Cl H H H H ClBr Br
Cl H H H H Br Cl HCl
Br HCl H HCl BrH Br Br
H Br
(A) Me
(A) Me Br (B)
Br (A)
(A) Me Me (B) Me Br(B)
Me
Br Cl (B)(C)
Cl Me ClBr
Me MeBr Me(C)(D)
(C) Br Cl(C) BrMe (D) BrMe
Br (D)Me (D) BrMe
Br Me Me
Ph Ph Ph PhPh Ph Ph PhPh Ph Ph Ph Ph Ph Ph Ph

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39. Ph  CH  CH2  CH3  Cl
hv
Pr oducts 
2 Fractional
Distillation
 Fractions,
|
CH3
(  or  )
No. of products and no. of fractions are respectively:
(A) 6, 5 (B) 6, 4 (C) 5, 4 (D) 6, 3

R 2 O2
40. 
hv
 Product

(A) (B) CHCl3 (C) both (A) and (B) (D)none of these

41. Which of the following will be the correct product of reaction?

Conc. H3 PO 4
 


(A) (B)

(C) (D)

H H Br 2
42. C=C=C A
CCl 4
C(CH3) 2CH2OH
H3 C
Product (A) in the above reaction is-
Br Br Br
H 3C H CH3 CH 3 CH 3 CH 3
(A) H C (B) H C
CH 3 (C) H (D)
3 O 3 O CH3 O CH 3 O Br
43. Which of the following compounds was starting material for the oxidation shown below?


KMnO /H
Compound   4

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

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MULTIPLE CORRECT ANSWER TYPE
H2 /Ni O3 /H2 O
1. C 4 H6   C 4 H8   CH3 COOH
(A) (B)

Hence A and B are:

(A)CH3—CC—CH3, CH3CH=CH—CH3 (B)CH2=CHCH=CH2, CH3CH = CHCH3

(C) , CH3CH = CHCH3 (D)None of these

2. Choose all alkane that give only one monochloro derivative upon reaction with chlorine in Sunlight

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

3. Monochlorination of (S)–2–chlorobutane can give

(A) (S)–1, 2–dichlorobutane (B) (R)–1, 2–dichlorobutane
(C) (2R, 3S)–2, 3–dichlorobutane (D) (2R, 3R)–2, 3–dichlorobutane
4. CH2 = CHCH2CH = CH2 NBS
 A, A can be
(A) CH2  CHCHCH  CH2 (B) CH2=CHCH=CH–CH2Br
|
Br
(C) CH2 = CH CH2 CH = CHBr (D) CH2  CHCH2 C  CH2
|
Br
5. Choose the correct statements regarding the given reaction:

m  CPBA H3 O
  A  B
(A)product A is optically active
(B)the conversion of alkene to product B is a stereospecific reaction
(C)product B has chiral molecule
(D) formation of ‗A‘ is syn addition reaction
6. Which of the following reactions are not feasible?
(A) HC  CH  KOH   (B) HC  CH  NaNH2 


O
(C) HC  CH  NaOH 
 (D) HC  CK   (CH3 )3 C  Br 

7. 1-butene is formed in reactions:

(A) (B)

OH
(C)  (D)


8. Predict the products of following reactions:

(A) A is Ph  CH2  CH2  CH2  CH3 (B) B is Ph  CH  CH  CH  CH2

(C) A is Ph  CH  CH  CH  CH2 (D)B is Ph  CH2  CH2  CH  CH2

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9. 1. NaNH2
H3 C  C  CH 
2. CH3 CH2 Br
 A  H2
Pd  BaSO 4
B :

(A) A is H3C  CH2  C  CH (B) A is CH3  C  C  CH2CH3

(C)B is (D)B is

10. Possible products formed during the reaction.

CH2 –Cl
Na (Dry ether)
CH2 –Cl
CH3

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

O
||
11. Ph  C  CH3 
X
 Ph  CH2  CH3 ; X could be
(A) H2 N  NH2glycol /OH (B) Na-Hg/concHCl
H2 C  CH2 ;
(C) Red. P/HI (D) | | Raney Ni  H2
SH SH
12. In the following reaction

C7 H12 (A) 

HBr
 ; A can be

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

13. Which of the following will give three different compounds on ozonolysis

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

14. Which of the following reaction can proceed via formation of a 6 member cyclic transition state
 
(A)  CH2  CH2   (B)  CH2  CH2  

 
(C)  CH2  CH2   (D)  CH2  CH2  

15. Which of the following reactions

OHgive alkylation product:
OH OH OH
(A)
(A)
(A) (A)
+ + +
(A) H + H H (B) H (B)
+ (B)
(B)H+
(B)
+
+ H H
H

AICI3 AICI3 AICI AICI AICI3 AICI3 AICI

AICI
(C)
(C)
(C) ++
CHCH
(C) 3COCI
3COCI + CH3COCI 3(D) 3
(C)+ CH3COCI + Me3C (D)
(D) (D)+ Me3C+
–(D)
COCI +–MeCOCI
Me3CC––
COCI
COCI
3
3 3

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16. Select correct statement(s)

(A) A is OsO4/aq. NaHCO3 (B) B is mCPBA/ H3 O

(C) C is obtained when D is heated with conc. H2 SO4 (D) Reaction C to Z is stereo non-selective

CH3
|
17. CH 2  CH  C  COOH 
NaOH
CaO , 
X , x can be
|
CH3
CH3 CH3
| |
(A) CH 2  CH  C  CD 3 (B) CH2  CH  C  H
| |
H CD3

(C) (D)

PARAGRAPH BASED QUESTIONS

PARAGRAPH FOR NEXT THREE QUESTIONS
Demercuration allows Mardownikoffs addition of H, OH without re arrangement. The net result is the
addition of H2O. Answer the following question.
CH3
i)Hg(OAc)2. THF HI (Conc.)
1. CH3 – C – CH = CH2 A B, Product B is :
ii)CH3OH, NaBH4NaOH
CH3

(A) (CH 3 )3 CCH  CH 3 (B) CH3 I (C) CH3CH2 I (D) (CH 3 )3 CCH  CH 3
| |
OH I
O

N–Br
1) Hg)OAc)2, THF
2) H2O OH
O
2. CH3CH = CH2 A B C.
3) NaBH4, NaOH
The product 'C' formation from B occurs through
(A) enol formation (B)SN1mechanism
(C) Neighbouring group particitation (D)SNAR mechanism
OH
3. i) Hg(OAC)2.THF
ii) NaBH4, NaOH
A,

Product 'A' is :
OH OH OH
OH OH OH OH
OH
OH OH OH
OH
(A) HO
(A) (A)
(A) HO HO
HO (A) (B) (B) (B)
(B)
(B) (C) (C)
(C) (C) (D) (D) (D)
(D)
OH OH OH (C)
OH (D)

OH
OH OH OH

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PARAGRAPH FOR NEXT THREE QUESTION
Consider the following figure representing variation of heat of combustion of isomeric butenes.

Based on this answer the following questions:

4. Minimum dipole moment is of isomers.
(A) P (B) Q (C) R (D) S
5. Which gives fastest reaction with HBr?
(A) P (B) Q (C) R (D) S
6. Which will give product showing no optical activity, when treated with HBr.
(A) P (B) Q (C) R (D) all of these

MATRIX-MATCH QUESTIONS
1. Match the following column
COLUMN I COLUMN II

(A) (P) Hofmann‘s alkene

(B) C H O /C H OH
(Q) Saytzeff‘s alkene

2 5 2 5



(C) (R) Transition state

(D) (S) Carbocation

2. Match the column I with column II:

COLUMN I COLUMN II
CH3
CH3
HgSO
4 
(A)  CD  CD
HgSO4
C   (P) OH
D2 SO4 D2 O D2SO4D2O *
14
CH3 CH3
CH2OH
H
* *
(B) 14 
H2SO4
 (Q) 14
H2O

CH3

*
(C) 14 B H /THF
2 6 (R) CD2CDO


OH /H2O2

B D /THF
2 6
(D) C  CD
C CD 
 (S) C  CD3
OD /H2O2
O
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NUMERICAL VALUE QUESTIONS
1. One mole of 1,2-Dibromopropane on treatment with x moles of NaNH2 followed by treatment with
ethyl bromide gave 2-pentyne) The value of 'x ' is
2. The number of moles of CH4 formed by reacting 96 grams of CH3 OH with excess CH3 MgI is
3. The maximum nubmer of carbon atoms in the expected products of the following reaction
CH3 CH2 Br  CH3  CH  CH 2 Br 
 Product Na/Ether

|
CH3
CH3
Cl 2 ,h
4. H C   M(C5H11Cl) (isomeric products).The number of M is
3
CH3
COOK

Kolbe 's electrolysis

5.  Pr oduct

COOK

How many secondary carbons are present in the product

6. The number of organic products (including by-products) formed when a mixture of chloroethane and
chloropropane is treated with sodium in dry ether is
7. The number of moles of ozone required for the reductive ozonolysis of 1 mol of the following
compound is
CH2

8. How many of the following reagents can be used to distinguish between hex-1-yne and hex-2-yne?
(a) CuCl/NH3 (b) AgNO3/NH3 (c) Na metal
(d) neutral FeCl3 (e) Fehling‘s reagent
9. The number of reagents among the following which cannot add to propene by free radical mechanism in
presence of organic peroxides is
(A) HCl (B) HBr (C) HI (D) CH3SH (E) BrCCl3
10. (a) CH3 CH C C CH CH3
(X)
OH OH

Total no. of stereoisomers of the product when above compound

(b) Total no. of stereoisomers of the product when above compound (X) is reduced by lindlar
catalyst.
(c) Total no. of stereoisomers of the product when (X) is reduced by Na/liq NH3 (Birch reduction)
Ans.a-3, b-3

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JEE MAIN
1. The reaction propene with HOCl (Cl 2  H2 O) proceeds through the intermediate: [2016]
(A) CH3  CHCl  CH2 (B) CH3  CH  CH2  OH
(C) CH3  CH  CH2  Cl (D) CH3  CH(OH)  CH2

2. Which compound would give 5-keto-2-methyl hexanal upon ozonolysis? [2015]

CH3 CH3 CH3 CH3
H3C CH3

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

CH3 CH3

3. Which branched chain isomer of the hydrocarbon with molecular mass 72u gives only one isomer of
mono substituted alkyl halide? [2012]
(A) Tertiary butyl chloride(B) Neopentane (C) Isohexane (D) Neohexane
4. 2-Hexyne gives trans-2-Hexene on treatment with [2012]
(A) Pt /H2 (B) Li /NH3 (C) Pd /BaSO4 (D) LiAlH4

5. Ozonolysis of an organic compound give formaldehyde as one of the products. This confirms the
presence of : [2011]
(A) a vinyl group (B) an isopropyl group
(C) an acetylenic triple bond (D) two ethylenic double bonds

6. The main product of the following reaction is : [2010]

conc. H2SO4
C6H5CH2CH(OH)CH(CH3)2  
H5C6 H C6H5 CH2 CH3 C6H5 CH(CH3 )2 H5C6CH2CH2
CC CC CC C  CH2
(A) H CH(CH3 )2 (B) H CH3 (C) H H (D) H3C

7. One mole of a symmetrical alkene on ozonolysis gives two moles of an aldehyde having a molecular
mass of 44 u. The alkene is : [2010]
(A) propane (B) 1-butene (C) 2-butene (D) ethene

8. In the following sequence of reactions, the alkene affords the compound ‗B‘
O H O
2  B, The compound B is :
3  A 
CH3CH=CHCH3  [2008]
Zn
(A) CH3COCH3 (B) CH3CH2COCH3 (C) CH3CHO (D) CH3CH2CHO

9. The hydrocarbon which can react with sodium in liquid ammonia is [2008]
(A) CH3CH2 C  CH (B) CH3CH = CHCH3
(C) CH3CH2C  CCH2CH3 (D) CH3CH2CH2C  CCH2CH2CH3

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JEE ADVANCED
1. The correct statement(s) for the following addition reactions is(are): [2017]
H3C H Br /CHCl
(i) 2 3  M and N

H CH3

H3C CH3
Br /CHCl
2 3  O and P
(ii) 
H H

(A) O and P are identical molecules

(B) (M and O) and (N and P) are two pairs of diastereomers
(C) Bromination proceeds through trans-addition in both the reactions
(D) (M and O) and (N and P) are two pairs of enantiomers
2. In the following monobromination reaction, the number of possible chiral products is [2016]
CH2CH2CH3
Br Br (1.0 mole)
2
H 
o

300 C
CH3
(1.0 mole)
Enantiomerically pure)

3. Among the following, reaction(s) which gives(give) tert-butyl benzene as the major product is(are)
[2016]
Br
Cl
(A)   (B)  
NaOC H 2 5 AlCl3

OH
(C) 
 (D) 

H2SO4 BF3.OEt2

4. Compound(s) that on hydrogenation produce(s) optically inactive compound(s) is(are) [2015]

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

5. In the following reaction, the major product is [2015]

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

6. The number of hydroxyl group(s) in Q is [2015]

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7. The reactivity of compound Z with different halogens under appropriate condition is given below:
OH monohalo substituted derivative when X2  I2

X2
dihalo substituted derivative when X 2  Br2

C(CH3 )3
Z
trihalo substituted derivative when X2  Cl2

The observed pattern of electrophilic substitution can be explained [2014]

(A) the steric effect of the halogen (B) the steric effect of the tert-butyl group
(C) the electronic effect of the phenolic group (D) the electronic effect of the tert-butyl group
8. Isomers of hexane, based on their branching, can be divided into three distinct classes as shown in the
figure

The correct order of their boiling point is [2014]

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

PARAGRAPH FOR NEXTQUESTION

P and Q are isomers of dicarboxylic acid C4H4O4. Both decolorize Br2/H2O. On heating, P forms the cyclic
anhydride.
Upon treatment with dilute alkaline KMnO4, P as well as Q could produce one or more than one from S, T
and U.

9. Compounds formed from P and Q are, respectively [2013]

(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

10. The carboxyl functional group (–COOH) is present in [2012]

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

11. The major product H of the given reaction sequence is [2012]


2 CN
4 H 95% H SO
CH3  CH2  CO  CH3  G 
Heat
(A) CH3  CH  C  COOH (B) CH3  CH  C  CN
| |
CH3 CH3

OH
|
(C) CH3  CH2  C  COOH (D) CH3  CH  C  CO  NH2
| |
CH3 CH3

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12. The number of optically active products obtained from the complete ozonolysis of the given compound
is:

[2012]
(A) 0 (B) 1 (C) 2 (D) 4
13. The total number of alkenes possible by dehydrobromination of 3-bromo-3-cyclopentylhexane using
alcoholic KOH is [2011]
14. The maximum number of isomers (including stereoisomers) that are possible on monochlorination of the
following compound, is: [2011]

15. The synthesis of 3 – octyne is achieved by adding a bromoalkane into a mixture of sodium amide and an
alkyne. The bromoalkane and alkyne respectively are [2010]
(A) BrCH2CH2CH2CH2CH3 and CH3CH2C≡CH (B) BrCH2CH2CH3 and CH3CH2CH2C≡CH
(C) BrCH2CH2CH2CH2CH3 and CH3C≡CH (D) BrCH2CH2CH2CH3 and CH3CH2C≡CH
16. The compound P, Q, and S

HNO 3
Where separately subjected to nitration using mixture. The major product formed in each case
H 2 SO 4
respectively, is: [2010]

(A)

(B)

(C)

(D)

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 ANSWER KEY

1. B 49. C 97. C 145. C 193. C

2. D 50. B 98. D 146. B 194. A
3. A 51. B 99. C 147. C 195. B
4. D 52. B 100. B 148. A 196. B
5. D 53. C 101. D 149. B 197. B
6. B 54. C 102. C 150. B 198. B
7. D 55. B 103. C 151. A 199. B
8. A 56. C 104. A 152. B 200. D
9. B 57. C 105. C 153. B 201. A
10. A 58. A 106. D 154. C 202. D
11. C 59. C 107. A 155. C 203. C
12. D 60. C 108. B 156. C 204. B
13. C 61. B 109. A 157. A 205. B
14. C 62. A 110. D 158. D 206. C
15. D 63. D 111. B 159. C 207. B
16. B 64. A 112. C 160. A 208. B
17. C 65. B 113. A 161. B 209. C
18. B 66. A 114. B 162. D 210. D
19. B 67. A 115. A 163. C 211. C
20. A 68. A 116. A 164. C 212. B
21. D 69. D 117. C 165. D 213. C
22. A 70. B 118. A 166. B 214. A
23. C 71. D 119. D 167. B 215. D
24. A 72. B 120. C 168. D 216. B
25. B 73. A 121. D 169. A 217. A
26. A 74. C 122. A 170. B 218. B
27. C 75. D 123. D 171. B 219. D
28. C 76. B 124. C 172. C 220. C
29. A 77. C 125. C 173. A 221. D
30. B 78. C 126. A 174. A 222. B
31. B 79. A 127. D 175. D 223. C
32. C 80. C 128. C 176. C 224. D
33. C 81. A 129. B 177. D 225. A
34. D 82. A 130. C 178. C 226. C
35. B 83. D 131. D 179. D 227. B
36. C 84. D 132. B 180. A 228. A
37. C 85. C 133. B 181. A 229. A
38. C 86. A 134. B 182. C 230. A
39. A 87. C 135. D 183. A 231. B
40. D 88. C 136. C 184. A 232. D
41. A 89. B 137. D 185. A 233. B
42. A 90. D 138. B 186. B 234. D
43. D 91. A 139. A 187. B 235. A
44. D 92. A 140. B 188. D 236. D
45. D 93. B 141. A 189. B 237. A
46. B 94. A 142. B 190. B 238. D
47. D 95. A 143. D 191. D 239. B
48. A 96. B 144. A 192. B 240. D

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241. B 245. A 249. A 253. C 257. D
242. C 246. D 250. C 254. A 258. D
243. B 247. C 251. B 255. B 259. C
244. A 248. C 252. A 256. B

SINGLE CORRECT ANSWERS

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

MULTIPLE CORRECT ANSWER

1. AB 5. BCD 9. BC 13. BD 17. ABCD
2. ABD 6. ACD 10. A 14. AB
3. BC 7. ABCD 11. ABCD 15. ABD
4. AB 8. AB 12. ABC 16. AB

PARAGRAPH BASED ANSWERS

1. B 2. C 3. A 4. D 5. B 6. D

MATRIX-MATCH ANSWERS
1. AQ,R,S; B Q,R; C P,R; D  P,R 2. AS; BP; CQ; DR

NUMERICAL VALUE ANSWERS

1. 3 2. 3 3. 8 4. 6 5. 8 6. 7 7. 6 8. 3 9. 2

JEE MAIN
1. C 2. C 3. B 4. B 5. A 6. A 7. C 8. C 9. A

JEE ADVANCED
1. BC 3. BCD 5. D 7. ABC 9. B 11. A 13. 5 15. D
2. 5 4. BD 6. 4 8. B 10. D 12. 0 14. 8 16. C

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