CHEMISTRY

HYDROCARBONS (ALKENES)

Level 1

1. (R)-3-bromocyclopentene (shown below) reacts with Br 2

/ CCl4 to form

two products, Y and Z, Y is not optically active (does not rotate plane-

polarized light). What is the structure of Y?

 A.

B.

C.

D.

Answer: C

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2. reactant (A)

can be :

A.

B.

C.

D. All of these

Answer: D

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3. major

product of the reaction is :

A.

B.

C.

D.
Answer: C

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4.

Which of the following products cannot be obtained in ozonolysis of o-

xylene?

CH O

A. ∣

CH O

O O

∣ ∣ ∣ ∣

B. CH 3 − C − C − H

O O

∣ ∣ ∣ ∣

C. CH 3 − C − C − CH3

O O

∣ ∣ ∣ ∣

D. CH 3 − C − C − CH O
Answer: D

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5. major

product of the reaction is :

A.

B.

C.

D.
Answer: B

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CH2 − CO2 K
electrolysis

6. ∣ −−−−−−−→ (A) (Kolbe electrolysis method) Product

( major )
CH2 − CO2 K

(A) of the reaction is :

A. CH 3
− CH3

B. CH 2
= CH2

C. CH 3
− CH = CH2

D. None of these

Answer: B

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7. products (C

) of the reaction is :

A.

B.

C.

D.
Answer: C

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8.

A.

B.

C.

D.

Answer: C

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9. The reaction of propene with H3 O
+
will proceed with which of the

following intermediates ?

A.

B.

C.

D.

Answer: C

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10. Which of the following bromides is the major product of the reaction

shown below, assuming that there are no carbocation rearrangement ?

A.

B.

C.

D.
Answer: D

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11. Which of the following reactions results in the formation of a pair of

diastereomers ?

A.

B.

C.

D.

Answer: B

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12. What is a likely product of the reaction shown ?

A.

B.

C.

D.
Answer: D

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13. Which of the following, when undergoing addition of HBr, will form

ONLY a pair of diastereomers ?

A.

B.

C.

D.

Answer: C

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14. How many transition states and intermediates will be formed during

the course of following reaction ?

A. 3 transition states and 3 intermediates

B. 4 transition states and 3 intermediates

C. 3 transition states and 2 intermediates

D. 5 transition states and 4 intermediates

Answer: B

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15. Product of which of the following reactions, is racemic mixture ?

 A.

B.

C.

D.

Answer: B

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16. The product(s) of the following reaction can best be described as :

A. a racemic mixture

B. a single enantiomer

C. a pair of diasteriomers

D. an achiral molecule

Answer: C

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17. Taking into account the stability of various carbocations and, as well as

the rules governing mechanisms of carbocation rearrangements, which

reaction is most likely to occur during the given reaction ?

A.

B.

C.

D. None

Answer: D

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18. Consider the following reaction in which the intermediate carbocation

loses H+ to give the final product



Which of the following energy profiles best represents the overall

reaction ?

A.

B.

C.

D.
Answer: D

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19. Methyl vinyl ether, H 2

C = CH – OCH3 , reacts with Br 2 / CH3 OH . If

methanol is reacting as water would, and if this reaction follows a typical

mechanism of electrophilic addition, what would be the expected product

A.

B.

C.

D.
Answer: B

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20. 2, 4-hexadiyne (C6H6) is allowed to react with Li in NH3(liq). The

product obtained is treated with 1 equivalent of Cl in

2
Cl4 . Which of the

following constitutional isomers are possible products ?

A. I and II

B. II and III

C. I and V

D. I and III

Answer: D

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21. Which of the following is the best stereochemical representation

when reaction between 1-methylcyclohexene and NBS react in aqueous

dimethyl sulfoxide ?

A.

B.

C.

D. None of these

Answer: B

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22. Which of the following is among the major products of the reaction of

(E)-3-methyl-2-pentene with BH3 in THF followed by the addition of

H2 O 2 / H O
−
?

A.

B.

C.

D.

Answer: A
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23. Compare rate of dehydration of (i), (ii) and (iii) by conc. H 2

SO4

A. (i) > (iii) > (ii)

B. (i) > (ii) > (iii)

C. (ii) > (i) > (iii)

D. (ii) > (iii) > (i)

Answer: B

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24. How many products will be formed in this reaction ?

A. 10

B. 2

C. 3

D. 4

Answer: B

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25.

Product (A) of the reaction is:

 A.

B.

C.

D.

Answer: B

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CH3

26. CH (A) , (A) is :

HF

3
− C H + H2 C = CH2 −−→
∘
∣ 2.5 C

CH3

A.
 B.

C.

D. CH 3
− CH − CH2 − CH = CH2
∣

C H3

Answer: B

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27. Predict the product (A) of the following reaction

 A.

B.

C.

D.

Answer: D

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28. Major-

product (A) is:

A.

B.

C.

D.

Answer: B
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29. Di-imide (N 2 H4 ) is used to reduce double bond of:

A. − C = O
∣

B. − C = N

C. − N O 2

D. − CH = CH −

Answer: D

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30.

End product of the reaction is :

 A.

B.

C.

D.

Answer: B

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31.

Product (A) is :

A.

B.

C.

D.
Answer: C

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32.

Product (A) is :

A.

B.

C.
 D.

Answer: B

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33.

Product (X) will be :

A.
 B.

C.

D.

Answer: A

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34.

Product (C) is :
 A.

B.

C.

D. P h − C = C − Ph

Answer: B

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35.

MMPP → Magnesium mono peroxy phthalate. Product (X) is :

A.

B.

C.

D.

Answer: B

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36. Product

(P) is :

A.

B.

C.

D. None of these

Answer: B
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37. Product

(A) is :

A.

B.

C.
 D.

Answer: B

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38. (no ring

substitution) product (A) is :

A. P h − CH2 − Cl

B. P h − CH2 − Br

C. P h − CH2 − CCl3

D. P h − CH2 − CBrCl2
Answer: B

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39.

metachloroperbenzoic acid Product (A) of the above reaction is :

A.

B.

C.
 D.

Answer: B

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

A.

B.
 C.

D.

Answer: B

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41. Which one of the following compounds gives acetone (CH3 ) C = O

2

as one of the product of its ozonolysis ?

A.

B.
 C.

D.

Answer: D

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42. Addition of HCI to 3,3-dimethyl-1-butene yields two products, one of

which has a rearranged carbon skeleton. Among the following

carbocations, select the possible intermediates in that reaction ?

A. 1,2

B. 1,3

C. 2,4
 D. 2,3

Answer:

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43. Conversion of cyclohexene to cyclohexanol can be conveniently

achieved by :

A. N aOH + H2 O

B. Br 2
− H2 O

C. hydroboration, oxidation

D. hydroboration hydrolysis

Answer: C

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44. Trans-cyclohexane-1,2-diol can be obtained by the reaction of

cyclohexene with:

A. KM nO 4

B. OsO 4

C. peroxy formic acid /H 3

O
+

D. SeO 2

Answer: C

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45. Bromination of (E)-2-butenedioic acid gives

A. (2R, 3S)-2, 3-dibromosuccinic acid

B. (2R, 3R)-2, 3-dibromosuccinic acid

C. a mixture of (2R, 3R) and (2S, 3S)-2, 3-dibromosuccinic acid

D. (2S, 3S)-2, 3-dibromosuccinic acid

Answer: A

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46. The major product formed during the reaction of 1-methyl

cyclopentene with CH 3
CO3 H is

A.

B.

C.

D.
Answer: C

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CH − CO2 H
electrolysis

47. , Product (B) of the

NaOH
∣∣ −−−−−→ (A) −−−−−−→ (B)
(two mole)

CH − CO2 H

reaction is :

A. CH 3
− CH3

B. H 2
C = CH2

C. H − C ≡ C − H

D. CH 2
= CH − CH = CH2

Answer: C

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48.

A.

B.

C.

D.
Answer: B

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49. Product

(P) is :

A.

B.

C.

D.
Answer: B

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50. What is the major product expected from the following reaction ?

A.

B.
 C.

D.

Answer: B

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Br2 / hv

51. CH 3 − CH = CH2 −−−−−−→ (A) , Product (A) of the reaction is :

(low conc.)

A. CH 3 − CH − CH2 − Br
∣

Br

B. H 2
C = CH − CH2 Br

C. CH 3
− C = CH2
∣

Br

D. Br − CH2 − CH2 − CH2 − Br

Answer: B

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52. Y is

A. O 3
/ Zn(H2 O)

B. H IO 4

C. CrO 3

D. Cold dil KmnO 4

Answer: A

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53.

Product of the reaction is:

A.

B.

C.

D.
Answer: B

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54. Which compound is a possible product from addition of Br2 to 1-

butene?

A.

B.

C.

D.

Answer: D

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55. Addition of Br to cis-2-butene would give a product which is:
2

A. achiral

B. racemic

C. meso

D. optically active

Answer: B

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56. Addition of Br to trans-2-butene would give a product which is

2

A. achiral

B. racemic

C. meso

D. optically active
Answer: C

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57. Addition of OsO to cyclopentene would give a product which is:

4

A. achiral

B. racemic

C. meso

D. optically active

Answer: C

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58. Addition of BH3 followed by H2 O 2 to trans-2-butene would give a

product which is:

 A. achiral

B. racemic

C. meso

D. optically active

Answer: B

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59. , Reagent A

may be :

A. H 2O /H
+

B. BH 3T H F / H2 O2 − OH
−

C. H g(OCOCH 3)
2
. H2 O / N aBr. N aOH

D. All are possible

Answer: C

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60. The major product of the following reaction is :

( C6 H5 CO ) O2 peroxide
2

CH3 − CH = CH2 + H Br −−−−−−−−−−−−−−→

A. CH 3 − CH2 − CH2 − Br

B. CH 3 CH (Br) − CH3

C. BrCH 2 − CH = CH2

D.

Answer: A

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61. Which of the following is a major product of the reaction shown

below?

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62. In methyl alcohol solution, bromine reacts with ethylene (ethene) to

yield BrCH 2, CH2 OCH3 in addition to 1, 2-dibromoethane because

A. the methyl alcohol solvates the bromine

B. the ion formed initially may react with Br or CH

−
3 OH

C. this is a free radical reaction

D. the reaction follows Markovnikov's rule

Answer: A

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63. Which of the following compound was the starting material for the

oxidation shown below?

A.

B.

C.

D.
Answer: B

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64. Which series of reactions will achieve the following transformation ?

A. 1 − Cl2 / CCl4 2 − Br 2

B. 1 − H Br 2 − Cl2 / CCl4

C. 1 − Cl2 / CCl4 2 − N BS / hv

D. 1 − N BS / hv 2 − Cl2 / CCl4

Answer: D

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65. Taking into account the stability of various cycloalkanes and

carbocations, as well as the rules governing mechanisms of carbocation

rearrangements, what is the most likely product of this reaction ?

A.

B.

C.
 D.

Answer: B

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66. A triene is treated with ozone followed by zinc in acetic acid to give

the following three products. What is the structure of the triene ?

A.

B.
 C.

D.

Answer: D

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67. Which of the following compound would yield trialkylborane shown

below when treated with BH 3 / T HF ?

 A. 2-methylbut-1-ene

B. 2-methylbut-2-ene

C. 3-methylbut-1-ene

D. 3-methylbut-1-yne

Answer: A

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68. If the following compound is treated with Pd/C in excess of hydrogen

gas, how many stereoisomers of the product will be obtained ?

 A. 1

B. 2

C. 3

D. 4

Answer: C

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69. Which is the most precise designation of stereochemistry for the

products formed in the electrophilic addition of DBr to 1-

methylcyclohexene ? (D =
2
H, an isotope of hydrogen)

A.

B.

C.

D. Both (a) and (b)

Answer: D

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70. Consider the addition of HBr to 3,3-Dimethyl-1-butene shown below.

What is the best mechanistic explanation for the formation of the

observed product ?

A. Protonation of the alkene followed by a hydride shift and addition

of bromide to the carbocation

B. Double bond shift in the alkene following by the protonation and

addition of bromide to the carbocation

C. Addition of bromide to the alkene followed by a double bond shift

and protonation

D. Protonation of the alkene followed by a methyl shift and addition of

bromide to the carbocation

Answer: D
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71. Propene CH3 CH = CH2 can be converted into 1-propanol by

oxidation. Indicate which sets of reagents amongst the following is ideal

to effect the above conversion ?

A. KM nO (alkaline)
4

B. Osmium tetroxide (OsO 4 / CH2 Cl2 )

C. B 2 H6 and alk.H 2 O2

D. O 3 / Zn

Answer: C

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72. Which is the most suitable reagent among the following distinguish

compound (3) from the others ?

(1) CH 3C ≡ C − CH3

(2) CH 3 CH2 − CH2 − CH3

(3) CH 3
CH2 C ≡ CH

(4)CH 3
CH = CH2

A. Bromine in carbon tetrachloride

B. Bromine in acetic acid solution

C. Alk. KM nO 4

D. Ammonical silver nitrate

Answer: D

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73. The principal organic product formed in the reaction given below is :
peroxide

CH2 = CH (CH2 ) COOH + H Br −−−−−→

8

A. CH 3 − CH Br(CH2 ) COOH
8

B. CH 2 = CH (CH2 ) COBr
8

C. CH 2 BrCH2 (CH2 )
8
COOH
 D. CH 2
= CH (CH2 ) CH BrCOOH
7

Answer: C

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74. When 2-butyne is treated with H 2

/ P d − BaSO4 , the product formed

will be :

A. cis-2-butene

B. trans-2-butene

C. 1-butene

D. 2-hydroxy butane

Answer: A

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 (i)X

75. CH 3
C ≡ CCH3 −−−−−−−−−→ H3 C − C − C − CH3

( ii ) H2 O / Zn ∣ ∣ ∣ ∣

O O

In the above reaction X is

A. H N O 3

B. O 2

C. O 3

D. KM nO 4

Answer: A

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76. Which of the following alkene on catalytic hydrogenation given cis and

trans-isomer ?

A.

B.
 C.

D. all of these

Answer: D

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77. In the reaction of hydrogen bromide with an alkene (in the absence of

peroxides), the first step of the reaction is the ............. to the alkene.

A. fast addition of an electrophilic

B. slow addition of an electrophile

C. fast addition of a nucleophilic

D. slow addition of a nucleophile

Answer: B
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78. Which of the following alcohols cannot be prepared from hydration of

an alkene ?

A.

B.

C.

D.

Answer: D

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79. Which of the species shown below is the most stable form of the

intermediate in the electrophilic addition ofCl in water to cyclohexene

2

to form a halohydrin ?

A.

B.

C.

D.

Answer: D
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80. The reaction, (CH3 ) C = CH2 + Br

2
⋅
→ (CH3 ) C − CH2 Br
2
is an

example of a/an ...... ........ step in a radical chain reaction.

A. initiation

B. termination

C. propagation

D. heterolytic cleavage

Answer: C

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81. Which of the following most accurately describes the first step in the

reaction of hydrogen chloride with 1-butene ?

A.
 B.

C.

D.

Answer: B

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82. Which of the following best describes the flow of electrons in the acid-

catalyzed dimerization of (CH 3

) C = CH2
2
?

A.

B.

C.
 D.

Answer: A

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83. Hydroboration of 1-methylcyclopentene using B 2 D6 , followed by

treatment with alkaline hydrogen peroxide, gives

A.

B.
 C.

D.

Answer: A

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84.

The correct statements with respect to the above pair of reactions are

that (I) the reactions are stereospecific (II) (X) is erythro and (Y) is
threoisomer (III) (X) is threo and (Y) is erythro isomer (IV) each of (P) and

(Q) gives a mixture of (x) and (Y)

A. I and II

B. I and III

C. I and IV

D. II and IV

Answer: A

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85. Identify .Q. in the following sequency of reactions :

A.
 B.

C.

D.

Answer: D

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86. 4-Pentenoic acid when treated with I and N aH CO gives :

2 3

A. 4,5-diiodopentanoic acid

B. 5-iodomrthyl-dihydrofuran-2-one

C. 5-iodo-tetrahydropyran

D. 4-pentenolyiodide

Answer: B

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87. Product

(B) of the reaction is:

A.

B.

C.

D.

Answer: B

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88. Product

(C) is :

A. P h − C ≡ CN a

B. P h − CH 2 − C ≡ CH

C. P h − C ≡ C − CH3

D. P h − CH = C = CH2

Answer: C

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89. Which of the following will give a mixture of cis and trans-1,4-dimethyl

cyclohexane, when undergo catalytic hydrogenation ?

 A.

B.

C.

D. Both (a) and (b)

Answer: D

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90. An optically active compound A with molecular formula C8 H14

undergoes catalytic hydrogenation to give meso compound, the

structure of (A) is :

A.

B.

C.

D.
Answer: B

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91.

How many products will be formed in above reaction ?

A. 2

B. 4

C. 3

D. 6

Answer: B

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92.

Product of the reacion is :

A. Racemic

B. Diastereomers

C. Meso

D. Pure enantiomers

Answer: A

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93. cis-2-butene −−−−−→ product , Product of the reaction is :

H Br

Peroxide

A. Racemic
 B. Diastereomers

C. Meso

D. E and Z isomer

Answer: A

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94.

Rate of reaction towards reduction using (H 2

/ P t) :

A. a b

B. a = b

C. b a

D. Reduction of given molecule is not possible

Answer: A

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95. Product A

of the above reaction is :

∣ ∣

A. R − C − R

B. R' − CH O

C. R − CO 2H

D. Both (a) and (b)

Answer: D

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96.

M CP BA → Metachloroperbenzoic acid

A.

B.

C.

D.

Answer: B

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97. Product of

the reaction is :

A.

B.

C.
 D.

Answer: A

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( 1 ) T H F : BD3

98. CH3 − CH = CH2 −−−−−−−−→ (A) Product (A) of the above

( 2 ) CH3 CO2 T

reaction is:

A. CH 3 − CH D − CH2 D

B. CH 3 − CH T − CH2 T

C. CH 3 − CH D − CH2 T

D. CH 3 − CH T − CH2 D

Answer: C

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99. Optically active isomer (A) of (C 5 H9 Cl) on treatment with one mole of

H2 gives an optically inactive compound (B) compound (A) will be :

A. CH 3 − CH − CH = CH2
∣

CH2 Cl

B. Cl − CH = CH − CH3
∣

CH3

C. CH 3 − CH − CH2 − CH = CH2
∣

Cl

D. CH 3 − CH2 − CH − CH = CH2
∣

Cl

Answer: D

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100. An organic compound C4 H6 on ozonolysis give

H CH O, CO2 , CH3 CH O . Compound will be:

A. H 2C = CH − CH = CH2
 B. CH 3
− CH = C = CH2

C. CH 3
− C = C − CH3

D.

Answer: B

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101. major

product of this reaction is :

A.
 B.

C.

D.

Answer: B

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CH3

∣ +
KmnO4 H H Br

102. CH 3 − CH −−−
− → (A) −
− → (B) −−−→ (C)

∣ Δ ROOR

CH3

Product (C) in the above reactions is :

A. CH 3 − C − Br
∣

CH3
 ∣

CH3

B. CH 3 − C − Br
CH3

C. CH 3 − C H − H
∣

CH2 − Br

D.

Answer: D

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CH3

103. Unknown (A)

HF

CH3 − C − CH2 + (CH3 ) CH CH3 −−→ C8 H18 (A)

2
273K

in the above reaction is :

A. 2, 2, 3-trimethyl pentane

B. 2, 2, 4-trimethyl pentane

C. 2,2-dimethyl hexane

D. n-octane

Answer: B
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104. Product

(Q) is :

A.

B.

C.

D.

Answer: B

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105.

Product (C) of the reaction is:

A.

B.

C.

D.

Answer: C
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106. What is the major product expected from the following reaction ?

A.

B.

C.
 D.

Answer: B

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107. Choose the correct product of this reaction :

A.
 B.

C.

D.

Answer: B

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108. A, Product

A is:

A.
 B.

C.

D.

Answer: D

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109. Choose the correct product of the following reactions :

 A.

B.

C.

D.

Answer: C

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110. How many stereoisomeric tetrabromides will be formed in the

following reaction ?

A. 2

B. 3

C. 4

D. 6

Answer: B

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111. How many stereoisomeric pentabromides will be formed in the

following reaction ?
 A. 2

B. 3

C. 4

D. None of these

Answer: A

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112. Identify

(Z) in the above sequence of reactions :

A.
 B.

C.

D.

Answer: B

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113.

major product (A ) of the above reaction :

A.

B.
 C.

D.

Answer: C

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114.

(only one enantiomer is taken) Which of the following statement is

correct about A and B ?

A. A and B are mixture of diastereomers

B. A and B are mixture of enantiomer

C. A and B are optically active

D. B is racemic mixture
Answer: A

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115.

A.

B.

C.
 D.

Answer: B

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116.

Product (Y) of the above reaction is :

A.

B.
 C.

D.

Answer: B

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N a / lig . N H3

117. In the reaction M e– C (Q), then Q is :

Br2

≡ C − Et −−−−−−−→ P −
− →
CCl 4

A. A pure compound which is optically inactive due to internal

compensation

B. A binary mixture which is optically inactive due to external

compensation

C. A binary mixture which is optically active

D. A pure compound which is optically inactive due to absence of

chiral centre
Answer: B

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118.

Which (π-bond) will reduce first, when above compound undergoes

catalytic hydrogenation ?

A. a

B. b

C. c

D. d

Answer: D
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119.

Major product (A) is :

A.

B.

C.

D.
Answer: C

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120. In the reaction given below, the product would be :

OH

+ ∣
H3 O

CH3 − CH = CH − CH3 −−
−→ CH3 − CH2 − CH − CH3

A. a mixture of diastereomers

B. optically active

C. optically pure enantiomer

D. a racemic mixture

Answer: A

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121. Surprisingly, the reaction shown below goes through classical

carbocation. What is the major product of this reaction ?

 A. trans-1, 3-dibromocyclohexane

B. cis-1, 3-dibromocyclohexane

C. trans-1, 2-dibromocyclohexane

D. cis-1, 2-dibromocyclohexane

Answer: B

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122. The major product of the reaction given below is :

A. (i) and (ii)

B. (iii) and (iv)

C. (v) and (vi)

D. none of these

Answer: C

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123. Which reaction will occur at the fastest rate ?

 A.

B.

C.

D.

Answer: D

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124. Above

reaction is known as:

 A. Wurtz reaction

B. Fittig reaction

C. Wurtz fittig reaction

D. Kolbe electrolysis

Answer: C

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∣ ∣

125. CH

RedP + H I

3
− CH2 − C − H −−−−−−→ A

Product A is :

A. propane

B. propanol

C. prapanoic acid

D. propene

Answer: A
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126. Which of the following compound give diastereomers when treated

with Br in CCl ?
2 4

A.

B.

C.

D.
Answer: D

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127. A mixture of C2 H6 , C2 H4 and C2 H2 is bubbled through alkaline

solution of copper (I) chloride, contained in Woulf's bottle. The gas

coming out is

A. original mixture

B. C2
H6

C. C2
H6 and C
2
H4 mixture

D. C2
H4 and C2 H2

Answer: C

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128. The

number of possible products for x and y is :

A. 2,4

B. 3,5

C. 3,6

D. 3,4

Answer: B

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129. Select the incorrect statement :

A. Bromine is more selective and less reactive

B. Chlorine is less selective and more reactive

C. Benzyl free radical is more stable than 2 free radical

∘
 D. Vinyl free radical more stable than allyl free radical

Answer: D

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130. Which of the following compound does not evolve CO2 gas, when

undergo oxidative ozonolysis ?

A.

B.

C. H 2C = CH − CH = CH2
 D.

Answer: D

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(a) (b)

131. cis-3-hexene −
− → meso 3,4-hexanediol trans-3-hexene −
− → meso

3,4-hexanediol. Choose pair of reagent (a, b) for above conversions.

A. Cold KmN O 4, OsO4

B. cold KmnO 4, RCO3 H / H3 O

O+

C. RCO 3H / H3 O
O+
cold KmnO 4

D. None of these

Answer: B

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132.

Product (C) of the above reaction is :

A. 1,3-hexadiene

B. 1,4-pentadiene

C. 1,3-butadiene

D. 1,3-heptadiene

Answer: B

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133. How many carbon-hydrogen bond orbitals are available for overlap

with the vacant p-orbital in ethyl carbocation ?

A. 0
 B. 3

C. 5

D. 6

Answer: B

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134.

To achieve above conversion, the reagents used will be :

A. O 3 / H2 O2 , H O
−
/Δ

B. H br, alcKOH , O 3, LiAIH4 , H

+
/Δ

C. H Br, t − buOK, O 3, KM nO4 , Δ

D. H Cl, KM nO (cold) , H
3
+
/Δ
Answer: B

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135.

A.

B.
 C.

D.

Answer: B

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136. Decreasing order of heat evolved upon catalytic hydrogenation of

given reactants with a H (Pd/C) is :

2
 A. b > c > a > d

B. d > a > c > b

C. d > c > a > b

D. c > b > c > d

Answer: B

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137.

The correct order of heat of hydrogenation of given molecules is :

A. d > c > a > b

B. d > c > b > a

 C. b > a > c > d

D. d > a > c > b

Answer: C

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138.

Product (A) of the above reaction is :

A.

B.
 C.

D.

Answer: B

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139.

Product (A) is :
 A.

B.

C.

D.

Answer: A

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140. What is the product of 1, 4-addition in the reaction shown below?

A.

B.

C.

D.

Answer: D

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141.

Dehydration of the above compound will give :

A. meso product

B. racemic mixture

C. diastereomer

D. optically pure enantiomer

Answer: B

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142.

What is stereochemistry of product ?

A. Racemic mixture

B. Optically inactive

C. Diastereomers

D. Meso product

Answer: A

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143.

End product formed in the above reaction is :

A. Optically active

B. Racemic

C. Meso

D. Diastereomer

Answer: D

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144. How many moles of BH are needed to react completely with 2 mole
3

of 1-pentene in hydroboration-oxidation reaction ?

A. 2 mole

B. 3 mole
 C. 2/3 mole

D. 3/2 mole

Answer: C

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145.

Product (B) in the above reaction is :

A.
B.

C.

D.
Answer: C

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14

146. H (?)

low conc of Br2

2
C = CH − CH3 −−−−−−−−−→
or high temp

Product of the above reaction is :

14

A. H 2
C = CH − CH2 − Br

14

B. H 2
C = CH − CH2 − Br

14

C. CH 2
− CH − CH3
∣ ∣

Br Br

D. Both (a) and (b)

Answer: B

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147. In which of the following reactions 1,3-butadiene will be obtained as a

major product ?
 ( CH3 ) COK ( 2 mole )

A. Br
3

− CH2 − CH2 − CH2 − CH2 − Br −−−−−−−−−−−−−→

( CH3 ) COH
2

B. H O − CH
concH2 SO4

2
− CH2 − CH2 − CH2 − OH −−−−−−→

C. H
H2 1 mole

2
C = CH ≡ CH −−−−→
N i2 B

D. All of these

Answer: B

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148.

Identify A.

A.

B. CH 3
− C H − CH O
∣

C H3

∣ ∣

C. CH 3
− C − cH2 CH3
 C H3

D. CH 3
− C = CH2

Answer: B

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149.

Product (A) is :

A.

B.
 C.

D.

Answer: B

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150.

Bromination take place at :

A. a
 B. b

C. c

D. d

Answer: A

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151. Which is incorrect statement about heats of combustion ?

A.

B.

C. Iso − bute ≠ > trans − 2 − bute ≠ > 1 − bute ≠

D. n − H exa ≠ < n − H ep tan e < n − Oc tan e

Answer: C

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152. Predict the major product of the reaction.

A.

B.

C.

D.

Answer: B

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153. product

of the reaction is :

A. Meso compound

B. Enantiomeric pair

C. Diastereomers

D. Optically pure enantiomer

Answer: B

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154.

Product (A) of above reaction is:

A. CH 3O CH − CH2 − CH2 − CH O
∣

C O2 H

C H2 H

B. CH 3
O − CH2 − C H − CH2 − CO2 H

C. CH 3
O − C H − CH2 − CH2 − CO2 H
∣

C O2 H

D. CH 3
O − CH − CH2 − CH2 − CH2 − CH O
∣

C O2 H

Answer: D

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155. Products,

Comment up on optical activity of products.

A. Diastereomers

B. Racemic mixture

C. Meso

D. Optically pure enantiomer

Answer: B

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156.

Addition of a mineral acid to an olefin bond leads to major product,

Identify it:

A.

B.

C.

D.

Answer: C
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157.

In polyenes that contain differently substituted (C=C) double bonds, it is

possible to hydrogenate chemeselectively one (C=C) double bond.

Product is :

A.
B.

C.
 D.

Answer: B

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158.

MCPBA → meta-chloro perbenzoic acid) Stereochemistry of the product

of above reaction is :

A. Meso
 B. Racemic

C. Diastereomers

D. Optically inactive due to absence of chiral center.

Answer: B

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159.

Identify product (P).

 A.

B.

C.

D.

Answer: B
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160.

A isomerise to B on addition of traces of acid H 2 SO 4 . Compound (B) is :

A.
 B.

C.

D.

Answer: C

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161.

Product (A) of the reaction is :

A.

B.
 C.

D. None of these

Answer: B

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162. Product

(A) is :
 A.

B.

C.

D.

Answer: C

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163. Which of the following reactions do not represent the major product

of given Birch reductions ?

A. (i), (iii), (vi)

B. (iv), (vi), (vii)

C. (iv), (v), (vi)

D. (i), (ii), (v), (vii)

Answer: B

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164.

Product (A) is:

A.

B.

C.
 D.

Answer: B

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165.

Correct statement about above reaction is:

A. A =cis-2-chlorocyclohexanol,

B. A = trans-2-chloro cyclohexanol,

C. A = trans-2-chlorocyclohexanol,

D. A = cis-2-chlorocyclohexanol,
Answer: C

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166. Predict

the major product:

A.

B.
 C.

D.

Answer: C

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167. Product

(A) is :
A.

B.

C.
 D.

Answer: C

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168. Major

product of the reaction is :

A.
 B.

C.

D.

Answer: B

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169.

stereochemistry of the product is:

A. Diastereomers

B. Racemic mixture

C. Meso

D. Pure Enantiomers

Answer: A

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170. Product/s

obtained is/are :

A. Diastereomers

B. Meso

C. Racemic

D. Optically pure enantiomers

Answer: B

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171. Product

(x) is :

A.

B.

C.

D.

Answer: B

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 CH3

∣ +
H

172. CH3 − CH2 − CH2 − CH2 − C − CH2 − OH −

− → A
∣ Δ ( major )

CH3

product (A) is :

A. CH 3
− CH2 − CH2 − CH2 − C = CH − CH3
∣

CH3

B. CH 3
− CH2 − CH2 − CH2 − C = CH2
∣

CH3

CH3

C. CH 3 − CH2 − CH − CH2 − C − CH2

∣

CH3

D. `none

Answer: B

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H Br

173. CH 3 − CH = CH − CH3 −−−−−−−−−−−−−−−−−−−−−−→

R2 O2 Δ (Anti-Markownikoff's addition)

Comment on optical activity of the products:

A. Racemic
 B. Diastereomer

C. Meso

D. Optically pure enantiomer

Answer: A

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174. Product

(al is :

A.
 B.

C.

D.

Answer: B

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175.

Alkene (A) will be :

A. cis-2-pentene

B. cis-2-hexene

C. cis-4-octene

D. trans-2-hexene

Answer: C

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176.

Product (A) is

A. trans-2-butane

B. cis-2-butene

C. 1-butene

D. Iso-butene

Answer: B

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177. In which of the following reactions, two products will be formed

other than phosphonium ylide (P OP h 3

)
 A.

B. CH 3 CH O + P h3 P = C − CH3 →
∣

CH3

∣ ∣

C. P h − C − H + P h 3 P = CH − P h →

∣ ∣

D. H − C − H + P h 3 P = CH − CH3 →

Answer: C

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178. To carry out the given conversions, select the correct option:

A. a = Ag2 O, b = Zn / CH3 CO2 H , C = LiAlH4

B. a = H2 O2 , b = CH3 − S − CH3 , c = N aBH4

 C. Both (a) and (b

D. None of these

Answer: C

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179. The product (A) of given alkoxymercuration de-mercuration is :

A.

B.
 C.

D.

Answer: B

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ON a
Δ
∣ +

180. CH
H C = CH H H2 Al 2 O3

3
− C = CH2 −−−−−→ −
− → −−−−−−→ −−→
pd − BaSO4

End product of the reaction is :

A. H 2C = CH − C − CH2
∣

CH3

B. CH 3 − CH = CH − CH = CH2
 C. H 2
= CH − cH = cH2

D. H 2
C = CH − CH2 − CH = CH2

Answer: A

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181. Major product of the given reaction is :

HI (excess)

H2 C = CH − CH2 − I −−−−−→
CCl 4

A. CH 3
− C H − C H2
∣ ∣

I I

B. CH 3
− CH − CH3
∣

C. CH 3 − CH2 − CH2 − I

D. I − CH2 − CdH2 − CH2 − I

Answer: B

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182. The rate constant for a reaction can be increased by a the stability of

the reactant or by b the stability of the transition state. Select the correct

choice for a and b.

A. decreasing, decreasing

B. increasing, decreasing

C. decreasing, increasing

D. increasing, increasing

Answer: C

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183. Major product of the given reaction is :

 A.

B.

C.

CH3

D. H 2
C = C − C H2 − CH2 − CH3

Answer: C

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184.

Major product (A) is :

A.

B.
 C.

D.

Answer: C

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185. In the given reaction, only one alkene undergo preferential oxidation

by electrophilic ozone. Identify product (P) of the given reaction:

 A.

B.

∣ ∣

C. CH 3 − C − CH2 − CH = C − CH2 − CH O
∣

Ome

OH

D. CH 3
− CH − CH2 − CH = C − CH2 − CH2 − OH
∣

Ome

Answer: B

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186. Product

(P) is:

A.

B.

C.

D.
Answer: D

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187. Major

product of the reaction is :

A.

B.

C.
 D.

Answer: B

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188. Product

(B) is :

OH O

∣ ∣ ∣

A. P h − CH − CH = CH − CH2 − C − H

B. P h − CH = CH − CH O

C. P h − (CH = CH )
2
− CH O

D. P h − (CH = CH )
3
− CH O

Answer: C
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189. Isobutene, in the presence of H2 SO4 , forms a mixture of two

isomeric alkene (C 8
H16 ) . The major alkene is :

CH3 CH3

∣ ∣

A. CH 3
− C − CH = C − CH3
∣

CH3

CH3 CH3

∣ ∣

B. CH 3
− C − CH2 − C H − CH2
∣

CH3

CH3 CH3

∣ ∣

C. CH 3
− CH − CH = CH − CH − CH3

CH3 CH3

∣ ∣

D. CH 2 = C − CH2 − CH2 − CH − CH3

Answer: B

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190. An unknown alkene (A) reacts with 3 mole of H2 gas in presence of

platinum catalyst to form 1-isopropyl-4-methyl cyclohexane. When

unknown alkene (A) is ozonized and reduced, following product are

obtained
O O O O O O

∣ ∣ ∣ ∣ ∣ ∣ ∣ ∣ ∣ ∣ ∣

H − C − H H − C − CH2 − C − C − CH3 , CH3 − C − CH2 − C

The alkene (A) is :

A.

B.
 C.

D.

Answer: B

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191.

Product (C) is :

A.

B.

C.

D. Both (a) and (b)

Answer: B

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192. The following reaction take place in high yields.

Use your knowledge of alkene chemistry to predict a product even

though you have never seen this reaction before

A.

B.

C.
 D.

Answer: B

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193.

What is the ratio of glyoxal to pyrualdehyde obtained in the above

reaction ?

A. 1 : 3

B. 3 : 1

C. 1 : 2

D. 2 : 3

Answer: C
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194.

Which of the following product cannot be obtained in above reaction ?

O O

∣ ∣ ∣ ∣

A. H − C − CH2 − C − H

O O

∣ ∣ ∣ ∣

B. CH 3 − C − CH2 − C − H

∣ ∣

C. CH 3 − CH − C − H
∣

CH O

D. None of these

Answer: C

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195.

Product (A) is :

A.

C H3 C H3

∣ ∣

B. CH 3 − C − C − CH3
∣ ∣

OH OH

∣ ∣

C. CH 3
− C − CH3

∣ ∣

D. CH 3 − C − C(CH3 )
3

Answer: B

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196.

Product (A) of the reaction is :

A.

B.

C.

D. None of these

Answer: A

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197.

Product (A) is :

A.

B.
 C.

D.

Answer: B

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198.

Arrange the above in the decreasing order of reactivity towards HBr :

 A. a gtbgtc

B. b gtagtc

C. b gtcgta

D. a gtcgtb

Answer: B

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199. Which reaction has the lowest ΔG or (Activation-Energy)?

+
+

A.

B.

C.

D.
Answer: D

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200. Which of the following will rearrange ?

A. 1

B. 1 and 3

C. All

D. 1,2,4

Answer: C

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201. Which of the following is most likely to undergo a favorable hydride

shift ?

A.

B.

C.

D.

Answer: A

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202. Energy profile diagram for dehydration of 2-butanol using conc.

H2 SO4 is given below:

Product (b) of above reaction is :

A. 1-butene

B. cis-2-butene

C. trans-2-butene

D. iso-butene

Answer: B

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203. How many alkene on catalytic hydrogenation given isopentane as a

product ?

A. A) 2

B. B) 3

C. C) 4

D. D) 5

Answer: B

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204. Which of the following would not rearrange to a more stable form?

A.
 B.

C.

D.

Answer: C

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205. Consider the following reaction.

In this reaction SbF acts as:

5
 A. an acid

B. a base

C. a nucleophile

D. an electrophile

Answer: D

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206.

Product (Z) is:

A.
 B.

C.

D.

Answer: C

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207.

Relation between (B) and (C) is:

A. Enantiomer

B. Diastereomer

C. Geometrical isomer

D. Meso

Answer: B::C

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208. The reaction of HBr with the following compound would produce :
 A.

B.

C.

D.

Answer: B

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209. is an

example of:

A. Nucleophilic addition
 B. Nucleophilic substitution

C. Electrophilic substitution

D. Electrophilic addition

Answer: C

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210. Olefins can be hydrogenated by :

A. A) Zinc and HCl

B. B) Nascent hydrogen

C. C) Raney Ni and H

D. D) Lithium hydride in ether

Answer: C

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211. What are the products obtained on hydroboration-oxidation of the

given alkene

A. I and III

B. II and IV

C. II and VI

D. III and V
Answer: D

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212.

Relation between A and B, C and D are :

A. Position, chain

B. Position, Functional

C. Chain, Identical

D. Metamer, Functional

Answer: B

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213. In which reaction syn addition doesn't take place.

 A.

B.

C.

D.

Answer: D

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H Br

214. Number of olefin of C4 H8 −

− → Number of Markonikow product
(X)
(y)

(including stereo) x+y is :

A. 5

B. 6

C. 7
 D. 8

Answer: C

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Level 2

1.

In each reagent box write a letter designating the best reagent and

condition selected from the above list of reagents.

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2. Propene (CH3 – CH = CH2 ) can be transformed to compounds (a to

j) listed in the left-hand column. Write letter designating the reagent, you

believe will achieve desired transformation. In the case of a multi step

sequence write the reagent in the order they are to be used.

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3. Match the column :

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4. Match the column I with column II and with column III (Matrix).

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5. Match the column I and II.

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

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7. C (exclude stereoisomer)
H2

2
F ClBrl −
− → (A)
Ni
(all isomers)

(2) (exclude stereoisomer) Total number of

H2

C4 H8 (alkene) −
− → (B)
Ni
(all isomers)

products (A) and (B) is equal to:

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8. How many

products are formed by sum of P,Q,R,S ?

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9. Vladimir Markovnikov rule : Alkenes undergo electrophilic addition

reactions. It is triggered by the acid acting as a electrophile toward t-

electrons of the double bond. Markovnikov's rule states that when an

unsymmetrically substituted alkene reacts with a hydrogen halide, the

hydrogen atom adds to the carbon that has the greater number of

hydrogen, e.g.,

Which of the following is most reactive toward Markovnikov addition ?

A.
 B.

C.

D.

Answer: B

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10. Vladimir Markovnikov rule : Alkenes undergo electrophilic addition

reactions. It is triggered by the acid acting as a electrophile toward t-

electrons of the double bond. Markovnikov's rule states that when an

unsymmetrically substituted alkene reacts with a hydrogen halide, the

hydrogen atom adds to the carbon that has the greater number of

hydrogen, e.g.,

What is the energy profile for the given reaction ?

A.

B.

C.
 D.

Answer: C

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11. Vladimir Markovnikov rule : Alkenes undergo electrophilic addition

reactions. It is triggered by the acid acting as a electrophile toward t-

electrons of the double bond. Markovnikov's rule states that when an

unsymmetrically substituted alkene reacts with a hydrogen halide, the

hydrogen atom adds to the carbon that has the greater number of

hydrogen, e.g.,

In which of following reactions carbocation rearrangement is possible ?

 A. (CH
HC l

3
) CH − CH = CH2 −
−→
2 ∘
O C

B. (CH
H Br

3
) C − CH = CH2 −−−−→
3
∘
0 C / C l4

C. ph − CH
H Br

2
− CH − CH2 −
−→
C C l4

D. All of these

Answer: D

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12. Vladimir Markovnikov rule : Alkenes undergo electrophilic addition

reactions. It is triggered by the acid acting as a electrophile toward t-

electrons of the double bond. Markovnikov's rule states that when an

unsymmetrically substituted alkene reacts with a hydrogen halide, the

hydrogen atom adds to the carbon that has the greater number of

hydrogen, e.g.,


Identify the major products r 1, r2 , and r 3 in the given reactions.

A.

B.

C.

D.
Answer: B

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13. Vladimir Markovnikov rule : Alkenes undergo electrophilic addition

reactions. It is triggered by the acid acting as a electrophile toward t-

electrons of the double bond. Markovnikov's rule states that when an

unsymmetrically substituted alkene reacts with a hydrogen halide, the

hydrogen atom adds to the carbon that has the greater number of

hydrogen, e.g.,

In which of the following reactions, product is racemic mixture ?

A. CH
H Br

3
− CH2 − CH = CH2 −
−→
C C l4

B.
 C.

D. All of these

Answer: D

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14. Vladimir Markovnikov rule : Alkenes undergo electrophilic addition

reactions. It is triggered by the acid acting as a electrophile toward t-

electrons of the double bond. Markovnikov's rule states that when an

unsymmetrically substituted alkene reacts with a hydrogen halide, the

hydrogen atom adds to the carbon that has the greater number of

hydrogen, e.g.,

In which of the following reactions, diastereomers will be formed ?

 A.

B.

C.

D. All of these

Answer: D

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15.
⊕
H

CH3 − CH2 − CH = CH2 + CH2 OH −

− → CH3 − CH2 − CH − CH3
∣

OCH3

What is electrophile in first step?

A. CH 3

B. H ⊕

C. CH 3 − CH2 − CH − CH3

D. H O ⊕

Answer: B

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16.
⊕
H

CH3 − CH2 − CH = CH2 + CH2 OH −

− → CH3 − CH2 − CH − CH3
∣

OCH3

What is nucleophile in first step?

 A. CH 3
OH

B. 1-butene

C. H 2
O

D. CH 3
− O − CH3

Answer: B

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17.
⊕
H

CH3 − CH2 − CH = CH2 + CH2 OH −

− → CH3 − CH2 − CH − CH3
∣

OCH3

What is electrophile in second step ?

A. CH 3 − CH2 − CH − CH2

B. H ⊕

C. CH 3 − CH2 − CH − CH2

D. CH 3 − CH2 − CH2 − CH2

Answer: C

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18.
⊕
H

CH3 − CH2 − CH = CH2 + CH2 OH −

− → CH3 − CH2 − CH − CH3
∣

OCH3

What is nucleophile in second step ?

A. CH 3 − CH2 − CH = CH2

B. CH 3 OH

C. H 2O

D. CH 3 − O − CH3

Answer: B

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19.
⊕
H

CH3 − CH2 − CH = CH2 + CH2 OH −

− → CH3 − CH2 − CH − CH3
∣

OCH3

Which step is rate determining step ?

A. attack of nucleophile CH 3 OH

B. attack of electrophile H ⊕

C. attack of nucleophile H 2O

D. attack of electrophile CH 3

Answer: B

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20. Match the column I and II :

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