CHEMISTRY HOUSE

11102024 Test Foundation Batch

ORGANIC CHEMISTRY
(Topic : GOC)
Time : 120 : 00 Min. Max. Marks :300
(for JEE-Mains & Advanced 2025)
* Each question + 4 (for correct answer) & - 1 (for wrong answer)
=============================================================================================================
01. The attacking reagent in the reaction
Me2 C = CH Me + HCl CCl
4 is :
*(a) H+ (b) Cl+ (c) H  (d) Cl 
02. The intermediate formed in the reaction Me HBr
 is :

+
(a) Me (b) Me *(c) + Me (d) Me
Br
Br Br
03. The major product formed in the reaction Ph CH = CH Me  is :
HCl
(a) Ph CH2 CH Cl Me (b) Ph CH = CH—CH2 Cl

(c) Cl — —CH = CH Me *(d) Ph CH Cl Et

04. The intermediate formed in the reaction PhCH = CMe2 + HBr, peroxide :
(a) PhCHCHMe2 (b) PhCH2CMe2 *(c) PhCHCMe 2
Br 
(d) PhCHBr CMe . 2

05. Which one of the following carbocations will not rearrange ?

+
CH2 CH3 CH3
+ + +
(a) *(b) (c) (d) CH3 ——CH——CH —CH3

06. The product of the reaction :

OH H+
X ; is :


(a) (b) *(c) (d)

07. Major Product :

(a) *(b) (c) (d) None of these

08. Correct order of dehydration of following compounds will be :

(a) 1 < 2 < 3 < 4 (b) 4 > 3 > 1 > 2 *(c) 4 > 2 > 1 > 3 (d) 1 > 3 > 4 > 2
page no # 11
09. Dehydration of the isomeric alcohols :

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

What will be the order of rate of reaction ?

(a) IV > III > II > I (b) I > II > III > IV *(c) IV > II > III > I (d) II > IV > I > III

10. In the given reaction

The major product is :

(a) *(b) (c) (d)

11. On acid catalysed hydration, 2-phenyl propene gives :

(a) 3-phenyl-2-propanol (b) 2-phenyl-1-propanol
(c) 1-phenyl-3-propanol *(d) 2-phenyl-2-propanol
12. Ionic reactions with organic compounds proceed through :
(A) Homolytic bond cleavage (B) Heterolytic bond cleavage
(C) Free radical formation (D) Primary free radical
(E) Secondary free radical
Choose the correct answer from the options :
(a) (A) only (b) (C) only *(c) (B) only (d) (D) and (E) only
13. Me2 CH—CH = CH2 + HCl , peroxide 
The attacking reagent in this reaction is :
(a) H+ and major product is 2O alkyl chloride
(b) Cl and major product is 1O alkyl chloride.
*(c) H+ and major product is 3O alkyl chloride
(d) Cl and major product is 3O alkyl chloride
14. The intermediate of the reaction 1—butene + HBr , peroxide  is :
EtCHCH Br 
+ +
(a) EtCH Me *(b) 2
(c) EtCHBrCH2 (d) Et CHCH2Br
15. The order of relative stability of the contributing structure is :

Choose the correct answer from the options given below :

*(a) I > II > III (b) II > I > III (c) I = II = III (d) III > II > I

16. Cyclohexene is _____ type of an organic compound.

(a) Benzenoid aromatic (b) Benzenoid non-aromatic

(c) Acyclic *(d) Alicyclic
17. The interaction between  bond and lone pair of electrons present on an adjacent
atom is responsible for :
(a) Hyperconjugation (b) Inductive effect
(c) Electromeric effect *(d) Resonance effect
page no # 12
18. Find out the major product from the following reaction.

conc. H 2SO 4
OH 

*(a) (b) (c) *(d)

OH
+
19. H Major product

In the above reaction, left hand side and right hand side rings are named as A and B
respectively. They undergo ring expansion. The correct statement for this process is :
(a) Ring expansion can go upto seven membered rings
*(b) Finally both rings will become six membered each.
(c) Finally both rings will become five membered each.
(d) Only A will become six membered.
20. The major product (P) of the given reaction is (where, Me is – CH3)
Me OH

Me H
  (P) Major Product
Me
Me Me Me Me
Me Me Me
Me
(a) (b) *(c) (d)
Me Me Me CH2
21. A specis having carbon with sextet of electrons and can act as electrophile is called
(a) carbon free radical (b) carbanion *(c) carbocation (d) pentavalent carbon
22. Peroxide effect is applicable in :
(a) HF (b) DCl *(c) TBr (d) HI
23. Addition of HBr to 2-methyl-1-propene in the presence of hydrogen peroxide mainly
forms :
(a) 1-bromobutane (b) 2-bromopropane
(c) 2-bromo-2-methylpropane *(d) 1-bromo-2-methylpropane
24. Me2C = CHCH2CH2CH = CH2 + DBr , peroxide  Product is :

*(a) (b) (c) (d)

25. The intermediate formed in the reaction Me2C = CHMe + HBr , No peroxide  is:
*(a) Me2+C—Et (b) Me2C—Et (c) Me2CHCH+Me (d) Me2CH—CHMe
26. The intermediate formed in the reaction CH3 CH2 CH = CH2 + DBr , peroxide 
(a) CH3 CH2 CH CH2 D (b) CH3 CH2 CH Br CH2
*(d) CH3 CH2 CH CH2 Br .
+
(c) CH3 CH2 CH CH2 Br
page no # 13
27. The intermediate formed in the reaction C = CH2 + HCl  is :

+ + + +
*(a) Me3C (b) Me2 CCl CH2 (c) Me2 CH CH2 (d) C —CH3

28. 1–butene HCl

 Major product (A) through intermediate (I) by the attacking
reagent (R). (A) , (I), (R) are :
(a) isobutyl chloride , carbonium ion, H+
+
(b) sec butyl chloride, cyclic chloronium ion, Cl
(c) n—butyl chloride, carbocation, proton .
*(d) 1—chloro—1—methyl propane, carbonium ion, proton .
29. Which of the following will give same product with HBr in presence or absence of
peroxide.
(P) Cyclohexene (Q) 1-methylcyclohexene
(R) 1,2-dimethylcyclohexene (S) 1-butene
(a) P , Q (b) Q , R (c) R , S *(d) P , R
30. The organic compound obtained during the addition of HBr to propene in the presence
of peroxide catalyst is :
(a) 2-bromopropane (b) 2-bromopropene
*(c) 1-bromopropane (d) 1-bromopropene
31. In which of the following can peroxide effect operate ?
(a) CH3CH2CH = CH2 + HCl *(b) CH3CH2CH = CH2 + HBr
(c) CH3CH = CH.CH3 + HBr (d) CH3CH2CH = CH2 + HI
32. The intermediate formed during the addition of HCl to propene in the presence of
peroxide is :
• +  
(a) CH3 CHCH2 Cl *(b) CH2 CHCH3 (c) CH3 CH2 CH2 (d) CH3 CH2 CH2
33. The addition of HBr is easiest with
(a) CH2 = CHCl (b) CHCl = CHCl (c) CH3 – CH2 = CH2 *(d) (CH3)2C = CH2
34. Peroxide effect is observed with the addition of HBr but not with the addition of HI
to unsymmetrical alkene because
(a) H-I bond is stronger than H-Br and is not cleaved by the free radical
(b) H-I bond is weaker than H-Br bond so that Iodine free radicals formation is
difficult.
(c) Bond strength of HI and HBr are same but free radicals are formed in HBr
*(d) Iodine free radical is not so reactive that it can cause homolysis of -bond.
35. When 3-phenylpropene reacts with HBr in the presence of peroxide, the major
product formed is :
(a) 2-bromo 1-phenylpropane (b) 1, 2-dibromo 3-phenylpropane
(c) 3-(o-bromophenyl) propene *(d) 1-bromo 3-phenylpropane
36. The peroxide effect involves :
(P) ionic mechanism (Q) free-radical mechanism
(R) heterolytic fission of double bond (S) homolytic fission of double bond
(a) P , R *(b) Q , S (c) P , S (d) Q , R

page no # 14
37. Which of the following statements are correct ?
(P) The addition of HBr to an alkene proceeds through ionic mechanism.
(Q) The addition of HBr to an alkene in the presence of peroxide proceeds through
ionic mechanism.
(R) Diphenylamine or catechol can prevent the abnormal addition of HBr to an alkene
in the presence of peroxide.
(S) Peroxide effect is applicable in HBr but not in DBr.
(a) P , Q *(b) P , R (c) R , S (d) Q , S
38. In the reaction, 1–pentene + DBr , peroxide, the intermediate formed is :
 
*(a) CH3CH2CH2 C HCH2Br (b) CH3CH2CH2 C HCH2D

CH3CH2CHCHCH2D
(c) (d) CH3CH2CH2CHCH2
Br Br
39. If 1 equivalent NaOH reacts with the given compound
COOH
(b)
COOH
(a) NO 2 OH
(c)
Choose the correct option :
(a) No reaction occurs *(b) NaOH reacts with –COOH (b)
(c) NaOH reacts with –COOH (a) (d) NaOH reacts with –OH
40. The negative part of the addendum adds on to the carbon atom joined to the least
number of hydrogen atoms. This statement is called
(a) Baeyer's strain theory *(b) Markovnikov’s rule
(c) Newmann theory (d)Peroxide effect
41. Which of the following compounds will give in the presence of peroxide a product
different from that obtained in the absence of peroxide?
(a) 1-butene , HCl (b) 2-butene,HCl *(c) 1-butene, HBr (d) 2-butene,HBr

42. Me CH = CH

Me
On reaction with DCl / Peroxide gives (A) as major product and the attacking re-
agent in this reaction is (R). (A) and (R) are :

*(a) CHD – CHCl Me , D

Me

(b) Me CHCl – CHD , Cl

Me

(c) Me CHD – CHCl , D

Me
–
(d) Me CHCl – CHD Me , Cl

page no # 15
43. Which of the following statements are correct for give reaction ?

(P) Major product is mixture of two enantiomers.

(Q) Less stable carbocation give major product.
(R) Less stable free radical give major product.
(S) More stable free radical give major product.
(a) P , R *(b) P , S (c) Q only (d) R only
44. Which among the following is correct?
(a) –Cl : –R effect (b) –CHO : +R effect (c) –OR : –R effect *(d) –COOR : –R effect
45. t-butyl ethylene on reaction with HBr-peroxide gives :
(a) 2-bromo-2-methyl butane (b) 1-bromo-3, 3-dimethyl butane
*(c) 2-bromo-3, 3-dimethyl butane (d) 3-bromo-2, 2-dimethyl butane
46. The most stable carbocation is :

+
+ +
+
(a) *(b) (c) (d)

47. 1–pentene + HI , peroxide  Product :

(a) CH3CH2CH2CH2CH2I (b) CH3CH2CH2CHIEt (c) Me2CHCHIMe *(d) EtCH2CHIMe
48. Which order is correct regarding the –I effect of the substituents ?
*(a) -NR2 < -OR < -F (b) -NR2 > -OR < -F(c) NR2 > -F > -OR (d) -NR2 > -OR > -F

49. i) HCl, peroxide ii) HBr, peroxide

  Product is :

Br
Cl

*(a) (b) Br
Cl

Br
Br

(c) (d)
Cl
Cl
50. The intermediate formed in the reaction

+ DBr, peroxide is :

Br D
*(a) (b) (c) (d)
Br D
51. The attacking reagent in the reaction Ph CH = CH2 + HCl , peroxide  is :
(b) H (d) Cl
+ +
*(a) H (c) Cl

page no # 16
 14
CH = CH CH2 Me
DBr (excess)
52. For the reaction peroxide
Me
Which of the following is/are correct :
(P) Product contains (n – 4) number of chiral carbons where ‘n’ is the DBE of the
product.
(Q) C14 is attached with ‘D’ in the product.
(R) Br is the attacking reagent. (S) D is the attacking reagent.
(a) P , Q (b) Q , R (c) Q , S *(d) P , R
53. Me3 C — CH = CH2 HBr,
 peroxide
 (A)
Me2 C = CH Me HCl,
  (B), (A) and (B) are :
peroxide

(a) primary alkyl bromide, secondary alkyl chloride

(b) secondary alkyl bromide, secondary alkyl chloride
(c) secondary alkyl bromide, t—alkyl chloride
*(d) primary alkyl bromide, t—alkyl chloride
54. Which of the following is false order of –I effect ?
  
(a) –F > –Cl > –Br > –I (b) – NR 3 > – NH3 > – NO2

(c) –F > –OH > –NH2 *(d) > –C = CH > –H

55. What is the correct order of inductive effect ?
(a) –O– > –CH3 > –CMe3 (b) –CO2– > –O– > CHMe2
*(c) –O– > –CH2Me > –D > –H (D) None
56. Select the correct statement.
(i) Delocalisation of s-electron is hyperconjugation.
(ii) Delocalisation of p-electron is resonance.
(iii) Permanent partial displacement of s-electron is inductive effect.
(A) i & iii (B) ii & iii (C) i & ii *(D) i, ii, iii
57. Which of the following has longest C – O bond :
O
O O O
(a) *(b) (c) (d)
CH2
NH 2
NH 2 NH 2
58. (I) (II) (III) (IV) CH2 = NH
CHO
Among these compounds, the correct order of C – N bond lengths is :
(a) IV > I > II > III (b) III > I > II > IV *(c) III > II > I > IV (d) III > I > IV > II
59. Which of the following molecule has longest C=C bond length ?
CH3
(a) CH2 = C = CH2 (b) CH3 – CH = CH2 (c) CH2–C–CH=CH2 *(d) CH3 – C = CH2

CH3 CH3
page no # 17
60. Among the following molecules, the correct order of C – C bond length is (C6H6 is
benzene)
(a) C2H6 > C2H4 > C6H6 > C2H2 *(b) C2H6 > C6H6 > C2H4 > C2H2
(c) C2H4 > C2H6 > C2H2 > C6H6 (d) C2H6 > C2H4 > C2H2 > C6H6
H H
2 3 4
61. H3C – C – CH – CH2 – H
1
CH2 = C – H
the correct order of bond dissociation energy (provided bond undergoes homolytic
cleavage):
(a) C2 – H > C3 – H > C4 – H > C1 – H (b) C2 – H > C3 – H > C1 – H > C4 – H
(c) C1 – H > C4 – H > C2 – H > C3 – H *(d) C1 – H > C4 – H > C3 – H > C2 – H
62. In which case, C – O bond length is shorter for Ist compound :

*(a) (b)

(c) (d)

63. Which species is NON aromatic ?

(a) *(b) (c) NH (d)

N N
64. Consider the following statements:
 
(I) CH3O C H2 is more stable than CH3 C H2
 
(II) Me2 C H is more stable than CH3CH2 C H2
 
(III) CH2 = CH - C H2 is more stable than CH3CH2 C H2
 
(IV) CH2 = C H is more stable than CH3 C H2
Of these statements:
(a) I and II are correct (b) III and IV are correct
*(c) I, II and III are correct (d) II, III and IV are correct
65. Consider the following carbocations
The relative stabilities of these carbocations are such that :


(A) (B) (C) (D) CH3 – C H2

*(a) D < B < C < A (b) B < D < C < A (c) D < B < A < C (d) B < D < A < C

page no # 18
66. Arrange the following carbocation in the increasing order of stability :

(I) (II) (III)

(a) I < II < III *(b) II < III < I (c) III < II < I (d) III < I < II
67. Select the correct order of stability of carbon free radicals :
  
I. Ph– C H2 II. Ph– C H–CH2–CH3 III. Ph– C H–CH=CH2 IV. Ph–C–CH=CH2
CH3
(a) IV > III > I > II *(b) IV > III > II > I
(c) I > II > III > IV (d) I > III > II > IV
68. CH2 = CH – CH = CH – CH3 is more stable than CH3 – CH = C = CH – CH3 because
(I) (II)
*(a) there is resonance in I but not in II.
(b) there is tautomerism in I but not in II.
(c) there is hyperconjugation in I but not in II.
(d) II has more cononical structures than I.
 
CH2 CH2

69. (I) (II)

CH3 CD3
Carbocation (I) is more stable than carbocation (II), because :
(a) —CD3 has more + I effect than —CH3 (b) —CH3 has more + I effect than —CD3
*(c) —CH3 has more + H effect than —CD3 (d) —CD3 has more + H effect than —CH3
Integer Type #

CH3 CH3
+
70.
CH3 – C — CH — C – CH3 H

CH3 OH H
The, total number of possible alkenes formed are ?
(Don’t consider stereoisomerism) Ans : 4
71. How many of of the following groups have –I effect :
(a) —OH (b) C OH (c) –CH3 (d) –OCH3 (e) –NH2 (f) –NO2
O
Ans : 5

page no # 19
72. In how many of the following, lone-pair indicated is involved in resonance :

(a) (b) N (c) (d) N

N N
H H

(e) CH2 = CH – CH2 (f) CH2 = CH – CH=NH Ans : 3
73. In which of the following lone-pair indicated is not involved in resonance :
 
(a) CH2 = CH – N H – CH3 (b) CH2 = CH – CH =O


(c) CH2 = CH – O – CH = CH2 (d) CH2 = CH – C  N


CH2
(e) (f) Ans : 3
O O
74. In how many second structure is more stable canonical structure in each of the fol-
lowing pairs :

(a) (b)

(c) (d)

(e) (f) Ans : 2

75. How many orders are correct for stability ?

(a)

(b)

(c)

CH3
(d) CH2 = CH – C > CH2 = CH – CH2 > CH3 – CH2 > CH2 = CH
CH3
Ans : 1
page no # 20