Navneet Jethwani: Organic Chemistry

FINAL TOUCH
REVISION
OF
ORGANIC CHEMISTRY
FOR JEE ADVANCED
BY
NAVNEET JETHWANI
HYDROCARBON
ETOOSINDIA
INDIA’S NO. 1 ONLINE COACHING
Plot No. 38, Near Union Bank of India, Rajeev Gandhi Nagar,
Kota, Rajasthan – 324005 Mob. : 9214233303
ETOOSINDIA F.T.R. BY N.J. SIR
Single Choice Exercise
1. Cl /h 
2
n  Butane  
Give the total number of monochloro products (including stereoisomers), which are possible in the reaction.
(A) 2 (B) 3 (C) 4 (D) 5
Ans. (B)
2. Double bond equivalent of cubane is
Cubane
(A) 4 (B) 5 (C) 6 (D) 7

Ans. (B)
Cl2
3. CH3 CH CH2 CH3 (x) = Number of monochloro product including stereoisomers.
h
CH3
(A) 4 (B) 5 (C) 6 (D) 7
Ans. (C)
ND2-ND2
4. (P)
H2O2
Product (P) is :
D D
(A) (B) (C) (D) both (B) & (C)
D D
Ans. (B)
H + H2 Pd
5. CH2
CH3
Product of the above reaction will be

(A) Racemic mixture (B) Diastereomers (C) Meso (D) Constitutional isomers
Ans. (B)
6. Among the following free radical bromination reactions, select those in which 2° halide is the major product -
CH2-CH3
Br2/h Br2/h Br2/h

(P) (Q) (R)
Plot No. 38, Near Union Bank of India, Rajeev Gandhi Nagar, Page # 2
Br2/h Br2/h
(S) (T)
Br2/h
(U)
(A) P,Q,R,S (B) P,R,U (C) P,R,S,T (D) P,Q,R,S,T
Ans (B)
7. Select the chain propagation steps in the free-radical chlorination of methane.

(1) Cl2  2Cl (2) Cl+ CH4  CH3Cl+H
(3) Cl  CH 4  CH 3  HCl (4) H + Cl2  HCl + Cl
(5) CH 3  Cl 2  CH 3Cl  Cl 
(A) 2,3,5 (B) 1,3,6 (C) 3,5 (D) 2,3,4
Ans. (C)
CH3
Br2/h Monobromo derivatives

8.
The number of possible monobromo products is (excluding stereoisomers) :

(A) 4 (B) 5 (C) 8 (D) 10
Ans. (B)
CH3 CH CH3 H /Pt

9. C C 2
D D
Product of the above reaction will be :

(A) Racemic mixture (B) Diastereomers (C) Meso (D) Constitutional isomers
Ans. (A)
10. Rank the transition states that occur during the following reaction steps in order of increasing stability
(least  most stable) :

1. H 3 C  O H 2  CH 3  H 2 O

2.  CH3 3 C  O H 2   CH3 3 C  H 2O

3.  CH 3 2 CH  O H 2   CH3 2 CH   H 2O
(A) 1 < 2 < 3 (B) 2 < 3 < 1 (C) 1 < 3 < 2 (D) 2 < 1 < 3
Ans. (C)
11. (R)-3 bromocyclopentene (shown below) reacts with Br2/CCl4 to from two products, Y and Z, Y is not optically active
(does not rotate plane-polarized light). What is the structure of Y ?
Br2 /CCl4
 Y  Z
Br
Br Br Br
(A) (B) (C)

Br Br
Br Br Br Br
Br
(D) (E)
Br Br Br
Ans. (C)
+
o H
12. Major product of the reaction :
OH
HO
(A) (B)
(C) OH (D)
OH
Ans. (B)
O3 H2/Ni H+
13. A B (C) ; Product (C) of the reaction is :
Zn 
OH O
(A) (B) (C) (D)
Ans. (C)
Br2
14. OH W. Product W is :
CH2Cl2
OH
(A) (B) Br
Br Br OH
OH
(C) Br (D)
O Br
Ans. (C)
15. What is a likely product of the reaction shown ?
H3C H
Br2 /CH3OH
CH3 
Br OCH3 H CH3
H3C CH3 H3C
H3C
Br OCH3
CH3
(A) (B) CH3 (C) (D) CH3
OCH3 Br
Br
Br
Ans. (D)
16. How many transition states and intermediates will be formed during the course of following reaction?
OH
+
H2O,H
(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
Ans. (B)
17. The product (s) of the following reaction can best be described as :
HBr
 
(A) a racemic mixture (B) a single enantiomer (C) a pair of diasteriomers (D) an achiral molecule
Ans. (C)
18. How many products will be formed in this reaction ?
1. OsO4
2.NaHSO3
(A) 10 (B) 2 (C) 3 (D) 4

Ans. (B)
cess)
H2 (ex
Pt CO2H
19. A KMnO CO2H
4
+
CO2H CO2H
Compound (A) is :
(A) (B) (C) (D)
Ans. (B)
20. What is the major product expected from the following reaction ?
KMnO 4
–
HO cold
OH OH
OH OH
OH H H
OH H O
(A) (B) H (C) OH (D)
Ans. (B)
21. Which of the following is a major product of the reaction shown below ?
CH3
Br2
H 2O
CH3 CH3 CH3 CH3

Br OH Br OH
(A) (B) Br (C) (D)
OH H H
H H OH Br
Ans. (D)
22. Which of the following compound was the starting material for the oxidation shown below ?
O
KMnO 4 /H  HO
?  OH + CO2
O OH
(A) (B)
(C) (D)
Ans. (B)

23. The reaction, (CH3)2C = CH2+ Br  (CH 3 ) 2 C  CH 2 Br is an example of a/an ........ step in a radical chain
reaction.
(A) initiation (B) termination (C) propagation (D) heterolytic cleavage
Ans. (C)
COOH
Br2
24. HOOC HOOCCH(Br)CH(Br)COOH
CCl4
(X)
P
Br2
HOOC COOH HOOCCH(Br)CH(Br)COOH
Q CCl4
(Y)
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 ismer
(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
Ans. (A)
O O
R' R
C C CH3 S CH3 Product A + CH3 S CH3
25.
H R dimethyl sulfide
O O
Product A of the above reaction is :

O
(A) R C R (B) R CHO (C) R  CO2 H (D) both (A) and (B)
Ans. (D)
CH3
H (1) BH3 ; THF (A) ; Product of the reaction is :
26.
–
(2) H2O2, HO
CH3 CH3 CH3 CH3

H OH H H
(A) H (B) H (C) OH (D) H
OH H H CH3
Ans. (A)
CH 3
1.BH 3/THF
27. – A ; Product A is ;
2. H 2O 2/OH
CH3 CH3 CH3

CH3
H H
(A) (B) (C) OH (D)
H OH
OH
OH H
Ans. (D)
CH 3
1.Hg (OAc)2.H 2O
28. A; Product A is ;
2. NaBH 4
CH3 CH3 CH3

CH3 OH
H
(A) (B) (C) OH (D)
H H
OH OH CH3 H
Ans. (D)
29. Choose the correct product of the following reactions :
O
CH3 Cl OOH
1.
+
CH3 2. H3O
OH
CH3
CH3 OH
(A) CH3 (B) OH
H CH3
CH3
OH
OH
CH3
(C) CH3 (D)
H
OH
CH3
Ans. (C)
30. Compound A, which is a degradation product of the antibiotic vermiculine has following structure
O O
C CH CH2 CH CH C
CH3 CH CH2 C OCH3
O
(A) H2 (B) (CH3)2S O3 (C) . Unknown (C) is :

C11H14O4 Pd/C C11H18O4 CH2Cl2 C11H18O2
CH2
C CH2 CH CH
(A) CH3 CH2 C C O CH3
CH2 O
CH2 O
C CH2 CH2 CH2 C
(B) CH3 CH2 CH2 C CH2 OCH3
CH2
CH2 O
C CH2 CH2 CH C
(C) CH3 CH2 CH2 C CH2 OCH3
CH3
(D) None of these

Ans. (B)
(a)
cis -3- hexene 
31.  meso 3,4 - hexanediol
(b)
trans-3- hexene   meso 3,4- hexanediol.
Choose pair of regent (A,B) for above conversions.
(A) Cold KMnO4 , OsO4 (B) Cold KMnO4, RCO3H/ H3O+
(C) RCO3H/H3O+ , cold KMnO4 (D) None of these
Ans. (B)
Na O3 Ph3P=CH2(2mole)
32. (A) (B) (C)
Liq. NH3 Zn
Product (C) of the above reaction is :

(A) 1,3 hexaidene (B) 1,4 pentadiene (C) 1,3 butadiene (D) 1,3 heptadiene
Ans. (B)
33.
To achieve above conversion, the regents used will be :

(A) O3/ H2O2, HO– / (B) HBr, alc. KOH, O3, LiAlH4, H+ / 
(C) HBr, t- BuOK, O3, KMnO4, (D) HCl, KMnO4 (cold), H+ /
Ans. (B)
1. Hg(OAc)2
34. A Product (A) of the above reaction is :
OH 2. NaBH 4
O O O O
(A) (B) (C) (D)
Ans. (B)
35. Decreasing order of rate of reaction of molecules towards electrophilic addition reaction is :
CH = CH2 CH = CH2 CH = CH2 CH = CH2
NO2 OH CH3 NH2

(a) (b) (c) (d)
(A) a > b > c > d (B) b > c > a > d (C) d > b > c > a (D) b > d > c > a
Ans. (C)
H2SO4
A;
36. 
OH
(A) (B) (C) (D)
Ans. (B)
37. Br2 Stereochemistry of the product is :

CCl4
H CH3
(A) Diastereomers (B) Racemic mixture (C) Meso (D) Pure Enantiomers
Ans. (A)
Br2
CCl4
38. Product/s obtained is / are :
H CH3
(A) Diastereomers (B) Racemic (C) Meso (D) Optically pure enantiomers
Ans. (B)
HO
39. H3O+
A
Product (A) of the reaction is :
OH OH
(A) (B)
(C) (D) None of these
Ans. (A)
40. Br2/hv Major (X) Alcoholic Major (Y) H-Br Major (Z):
KOH/ Peroxide
Product (Z) is :
Br
Br
Br
(A) (B) (C) (D)
Br
Ans. (C)
41. The reaction of HBr with the following compound would produce :
OH
Br
OH OH
(A) (B)
Br
Br
Br Br
(C) (D)
Br
Ans. (B)
O
C CH3 (1)3NaNH 2
PCl5 min eral oil
42. 
0 C
 (A) 
(2)H 
 (B) ; Product (B) is
70 80% 46%
CH CH2 C CH CH2
(A) (B) (C) (D)
Ans. (B)
Br2 (i)alc.KOH
43. 
CCl 4
 
(ii) NaNH 2
 (A) ; Product (A) is :
major
(A) H2C = CH – CH= CH2 (B) CH3 – C  C – CH3 (C) CH3 – CH2 – C  CH (D) CH3 – CH = C = CH2
Ans. (B)
O
NaNH 2 H
44. CH3CH2C  CH 
liq.NH3
I J  (K)
Et2O
Product (K) of the above reaction is :
O OH
C C Et
(A) C C Et (B)
OH OH
C C CH2 CH3 C C CH3
(C) (D)
Ans. (B)
(CH3 ) 2 SO4
45. CH 3  CH 2  CH 2  C  CH  LiNH 2 
(A)  (B)
Lithium
amide
Give the structural formula of compound (B) :

(A) CH3 – (CH2)2 – C  C – SO3H
(B) CH3 – (CH2)2 – C  C – CH3
O
(C) CH3 – (CH2)2 – C  C – CH2 – O S H
O
(D) CH3 – CH2 – C  C – CH2

Ans. (B)
CH2 CH2 CH3
46. ; This conversion can be achieved by :
(A) NaNH2, CH3CHO (B) NaNH2, CH3 – CH2 – CH2 – Br
(C) KOH, CH3 – CH2 – Br (D) KOH, CH 2 CH2
Br Br
Ans. (B)
Cl
3NaNH 2
47. Ph C CH3   (A) ; Product (A) is ;
Pr oduct
Cl

(A) Ph – CH = CH2 (B) Ph – C  CH (C) Ph – CH2 – CH3 (D) Ph C CNa
Ans. (D)
(i )NaNH 2 ,NH 3 H2
48. C CH (ii )CH 3Br
(A) 
Lindlar catalyst
(B) ; Product (B) is
H H
H CH3 C
C C CH3 C H
C C
(A) (B) H (C) C H (D)
C H
CH3
Ans. (C)
49. What is the final product, C, of the following reaction sequence ?
1.N aNH 2
H  2.CH
  
3 CH 2 Br
A
1.Na, NH3 (liq.)

A  B
Br2
B 
CH2Cl2
C
Br Br
Br
(A) (B)
Br
Br Br
(C) (D)
NH2 Br
Ans. (A)
Compound (X)
5H2 CH2 CH2 CH2 CH3
Pt
AgNO3
50. Precipitate
O O O O O O
O3 CHO
H C CH2 CH2 C C H + H C C O H + H C O H +
Me2S CHO
Compound (X) will be :
(A) CH CH C CH (B) CH CH2 C CH
(C) CH CH2 C CH (D) C CH C CH
Ans. (A)
51. How much volume of air will be needed for complete combustion of 10 lit. of ethane -
(Assuming that approx 20% O2 is present in air)
(A) 135 lit. (B) 35 lit. (C) 175 lit. (D) 205 lit.
Ans. (C)
52. During the preparation of ethane by Kolbe’s electrolytic method using inert electrodes the pH of the electrolyte -
(A) Increases progressively as the reaction proceeds
(B) Decreases progressively as the reaction proceeds
(C) Remains constant throughout the reaction
(D) May decrease of the concentration of the electrolyte is not very high
Ans. (A)
O
53. COOH ; A can be
O3 /H 2O
Alkene A 
 CH3 C CH3 + CH3COOH + CH3 C
O
CHCH 3 C(CH 3)2

CH 3
(A) CH3 C CH C (B) CH3 C CH HC CH 3
CH 3
(C) Both correct (D) None is correct

Ans. (C)
H
Ph CH3 Br2 NaI
54. 

 P(Alkene) 
CCl4
 
Acetone
Q(Alkene)
H3C Ph
OCOR
Alkene (P) & (Q) respectively are
CH 3 Ph CH 3 CH3 CH3
Ph
(A) Both C C (B) C C , C C
Ph H 3C Ph Ph Ph
H 3C
H
Ph CH3
CH3 CH3
(C) C (D) Both C C
Ph Ph
Ph CH2
Ans. (C)

H3O
55.
BH 3 / THF
B  CH2  A
H 2O2
A and B are
(A) Both CH2OH (B) Both CH3

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

OH OH
Ans. (D)
CCl3Br
56. CH2=CH–CH=CH2 
Peroxide
 Product. The major product is
(A) Br – CH2–CH=CH–CH2–CCl3 (B) CH 2 CH CH CH 2 CCl3
Br
(C) CH2 CH CH CH2 Br (D) None is correct

CCl3
Ans. (A)
OH
 (i)O3
H
57. 

A 
(ii) Zn/H 2O
 Product(s). Product is / are ?
CHO
(A) + HCHO (B) CH O

O
O
CHO
(C) + CH3CHO (D) OHC
Ans. (B)
58. ( reagent R 2 Reagent R1

   
HO OH HO OH
R1 and R2 respectively are –

(A) Cold alkaline KMnO4, OsO4 / H2O2 (B) Cold alkaline KMnO4 , HCO3H
(C) Cold alkaline KMnO4 , CH3 – O – O – CH3 (D) C6H5CO3H, HCO3H
Ans. (B)
COOCH3
OSO 4 (leq)
59. 
H 2 O/ Acetone
X .
COOCH3
Identify ‘X’.
COOCH3 COOCH3
OH OH
(A) OH (B)
COOCH3 OH
COOCH3
COOCH3
OH OH
(C) OH OH (D) Reaction will not occur
COOCH3
Ans. (B)
60. Identify (P) in the following reaction :
Ph H H
+2
H  /H 2O
  (P)
O
Ph Ph Ph O Ph
(A) (B) O (C) (D) O
O O O
O O
Ans. (A)
61. A mixture of CH4, C2H4 and C2H4 gaseous are passed through a Wolf bottle containing ammonical cuprous chloride.
The gas coming out is
(A) Methane (B) Acetylene
(C) Mixture of methane and ethylene (D) Original mixture
Ans. (C)
62. An organic compound of molecular formula C4H6, (A), forms precipitates with ammonical silver nitrate and ammonical
cuprous chloride. ‘A’ has an isomer ‘B’, one mole of which reacts with one mol of Br2 to form 1,4–dibromo-2-butene.
Another isomer of A is ‘C’, one mole of C reacts with only 1 mol. of Br2 to give vicinal dibromide. A, B & C are
(A) CH3 – CH2 – C  CH and CH2 = CH – CH = CH2;
(B) CH3 – C  C – CH3 and CH3 – CH = C = CH2 ; CH3 – C  C – CH3
CH2 CH2 CH
(C) C CH2 and ; CH2 = CH – CH = CH2
CH2 CH2 CH
CH
(D) CH3 – C  C – CH3 and CH2 CH2 ; CH = CH – CH = CH
2 2
CH
Ans. (A)
63. Correct statement regarding product of reaction
+ H Br
(1 eq)
(A) Kinetic controlled product is a secondary bromide whereas thermodynamically controlled product is a tertiary
bromide.
(B) Kinetic controlled product is a tertiary bromide whereas thermodynamically controlled product is a primary
bromide.
(C) Both kinetic & thermodynamic controlled product is secondary bromide.
(D) Both kinetic & thermodynamic controlled product is tertiary bromide.
Ans. (B)
HgSO4 (1)NH3  HCN

64. H  C  C  H 
H 2SO4
(A) 
(2)H O 
(B) ; Product (B) of given reaction is :
3
(A) Glycine (B) Alanine (C) Valine (D) Leucine

Ans. (B)
65. The slowest chain propagation step of the following reaction is
R 2 O2
CH4 + SO2Cl2   CH3Cl + SO2 + HCl
(A) RO   CH 4 
 ROH  CH 3 (B)  CH 3  SO 2 Cl 2 
 CH 3Cl   SO 2Cl
(C) SO 2 Cl 
 SO 2  Cl (D) Cl  CH 4 
 HCl  CH 3
Ans. (D)
66. Observe the following diagram for relative boiling points of different alkanes. Identify the hydrocarbons X, Y, Z, W,
R.
Z
W
X
R
Y
B.P.
alkanes
X Y Z W R
(A)
(B)
(C)
(D)
Ans. (B)

H  C  CNa NaNH 2 I  (CH 2 )7  Cl NaCN H 3O H 2 /Pd/CaCO 3 /Quinoline
67. E  (1)
 
(2)
 (3)
 
(4)
 
(5)
  (6)
F (CH2)7 H2C CH2 (CH2)6 COOH

C C
H H
Identify the compound ‘E’.
(A) 1-Fluorodecane (B) 1-Bromo-8-Fluorooctane
(C) 1-Bromo-7-Fluoroheptane (D) 1-Bromo-11-Fluoroundec - 2- yne
Ans. (B)
13
68. The compound ‘X’ OH can be synthesized by using the reagents.
13  13
Li
(I) + CH3MgBr (II) +O
O
 
O + Li13 Li
(III) (IV) +
O
(A) I and III (B) I, II, III (C) All (D) I, II only
Ans. (B)
69. The correct sequence of reagents for the following conversion is
OH
Hg(CH3COO) 2 / H 2O NaBH 4 Al2O3 dil.H 2SO 4 B2 H6 /THF H2O2 /OH dil.H 2SO4 
conc.H 2SO4
(A)  (1)
 
(2)

(3)
  (4)
 (B)  (1)
 
(2)
 (3)
 (4)
dil.H 2SO 4 Al2O3 ,  B2 H6 /THF H 2O2 /OH  dil.H 2SO 4 dil.H 2SO 4 /  Hg (CH 3COO) 2 /H 2O NaBH 4
(C)  (1)
 
(2)
  (3)
 (4) (D)  (1)
  (2)
  (3)
 
(4)

Ans. (C)
70. Which common factor is responsible for the regioselective nature of the following reactions.
Cl Cl Cl
Cl
HCl
(I) CH2 = CH – Cl    CH3 – CHCl2 (II) Cl2 /FeCl3
  +
Cl
Br Br

HBr NO 2
(III) H – C  C – Br    CH2 = CBr2 (IV)  
NO2
(A) – I effect of halogens (B) + I effect of halogens

(C) + M effect of halogens (D) – M effect of halogens
Ans. (C)
71. In which of the following reaction the product will also be optically active
H 2 /Pd/CaCO3
* O3
(A) *   (B)  
H 2 /Ni O3
(C) *   (D)  
*
Ans. (D)
(1) NaoH
72. + (x) 
(2)H 
 O ; Reactant x is
(A) CH3Cl (B) CH2Cl2 (C) CHCl3 (D) CCl4
Ans. (C)
CHFBrI
73. 
t.BuOK
(Q)
What is the product (Q) of the following reaction ?
Cl Cl
(A) (B)
(C) (D)
Cl F
Ans. (D)
H
* C
C  
K O C(CH 3 )3
74. Br Heat
(A)
Br * 14
(C C)
* Br * Br
(A) C C (B) C C
(C) C C (D) C C
Br
Ans. (B)
CHCl3 CHCl3
75. 
KOH
(A) 
KOH
(B) ; Product (B) is :
Cl
Cl Cl
(A) (B)
Cl
Cl Cl
Cl
(C) (D)
Cl
Ans. (C)
76. The major product formed in the following reaction is

Me Me
 :CH 2 (singlet) 

H H
Me H
Me Me
(A) (B)
H H H Me
Me CH2CH3
(C) 50 : 50 mixture of above two compounds (D)
H H
Ans. (A)
O
CH2 
Br2
(A)  CHBr3 
77. KOH
O
Product (A) of the reaction is :
CO2H CO2H CO2 CH3
(A) (B) (C) (D)
CO2H C CH3 CO2 CO2H
O
Ans. (C)
Multiple Choice Questions
H 3 (B)
/liqN
Li
1. NaNH 2 CH 3  I H2
CH 3  C  C  H   (A) (C)
Pd-CaCO3
Relation between (B) and (C) is:

(A) Enantiomer (B) Diastereomer
(C) Geometrical isomer (D) Meso
Ans. (B),(C)
Cl
2. Na
(A) ; Product (A) is :
14 dry ether
14 14
14
14
14
(A) (B) (C) 14 (D) 14
14
Ans. (A,B,C)
H2 /Pt O3 /H 2O
3. (A)C4H 6  (B)C4 H8   CH3COOH
Hence A and B are

(A) CH3C  CCH3 , CH3CH = CHCH3 (B) CH2 = CHCH = CH2 , CH3CH = CHCH3
(C) , CH3CH = CHCH3 (D) None
Ans. (A, B)
4. CH3 – CH = CH – CH3 + CH2N2 

 A ; A can be
(A) (B) (C) (D)

N N
N N
Ans. (A, B, C, D)
Peroxide
Ph – CH = CH2 + BrCCl3 
5.   Product is
H H Br
CCl3
(A) Ph CH2CCl3 (B) Ph CH2Br (C) Ph CH2CCl3 (D) Ph CH2Br
Br CCl3 H
H
Ans. (A, C)
6. Which of the following elimination reactions will occur to give but-1-ene as the major product ?
EtOH
EtOH
(A) CH3.CHCl.CH2.CH3 + KOH   (B) CH3.CH.CH2.CH3+NaOEt 

NMe3
+
(C) CH3.CH2.CHCl.CH3 + Me3COK+ 


 (D) CH3.CH2.CH(OH).CH3 + conc. H2SO4 


Ans. (B, C)
OH–
7. +
N
The above compound undergoes elimination on heating can yield which of the following products ?
(A) (B) (C) (D)

Me
+ CH2 CH2 Me
N N N N
Me Me Me Me Me Me Me
Me
Ans. (B, C, D)
8. Identify reagent for conversion of butene to butan-2-ol
(A) KMnO4/OH– / H2O(Cold) (B) Dil.

H2SO4
(C) (1) Hg(OAc)2/H2O (D) HOH/HgSO 4

(2) NaBH4
Ans. (B, C)
9. In which of the following cyclic transition state is formed.
500 C
(A) CH3 COOCH CH2 CH3   CH2 = CH – CH2CH3 + AcOH
CH3
(i)B2O6 /THF
(B) CH3 – CH = CH – CH3   CH3 CH CH CH3
(ii)H 2O2 /OD
D OH
CH2 N 2 /h
(C)  
HgSO4
(D) CH3 – C  C – Ph 
H 2SO4 /H 2O
 CH3 CH2 C Ph
O
Ans. (A, B, C)
10. Which of the following are correct :
1. O 3
(A) 2. Zn,H2O OHC – CH2CH2CH2 – CHO
H H
O
C6H5C OOH
(B) CH 2Cl 2 H H
H H O
KMnO4
H H
(C) cold dilute solution
H H
OH OH
O O
KMnO 4
(D) OH , heat
O CCH2CH2CH2C O
H H
Ans. (A, B, C, D)
11 Select correct statement :
(A) Methane cannot be prepared by catalytic hydrogenation of alkene
(B) Al isomers of the formula C6H14 can be prepared by catalytic hydrogenation of alkene
(C) All isomers of the formula C5H12 can be prepared by catalytic hydrogenation of alkene
D H2
(D) Ni product obtained show no optical rotation
D
Ans. (A, B, D)
12. Which of following reaction product is Diastereomer.
CHO
Br2 (i)NaCN
(A) CH3 (B) D H
CCl4 (ii)H+
CH3
CH3 CH3
HBr HCl
(C) C=C
CCl 4
(D) CH3 CH CH=CH Ph peroxide
H H Et
Ans. (A, B, D)
13. Which of the following produce aromatic product.

Red hot
(A) Me – C  CH Fe tube
(B) C6H14
NH2
CHCl 3
CHO
(C) KOH (D) + 

NH2 CHO
Ans. (A, B, C)
14. Which of the following represent correct product formation.
O
O CH2SH
Zn - Hg
(A) CH2SH (B)
N HCl N
H2 Raney Ni/
H H
O
O
NH2-NH2
(C) Red P (D) EtOK
Hl (excess) N N
H H
Ans. (A, C, D)
15. Suitable reagent(s) to carry out following conversion is/are
O
N C CH3 N Et
CH3 CH3
CH2 SH
(A) /H2/Ni followed by OH (B) N2H4 /H2O2
CH2 SH
(C) N2H4 / EtONa (D) Zn / Hg / HCl
Ans. (A, C)
16. What are the possible intermediates in the following reaction ?

(1)Br2  CCl4
CH3  CH 2  CH  CH 2 
(2) NaNH2 / 
 CH3  CH 2  C  CH
(A) CH3 CH2 CH CH2Br (B) CH3CH2 CH CHBr

Br

(C) CH3 CH2 C CH2 (D) CH3  CH CH  CH  Br
Br
Ans. (A, B, C)
17. When is reacted with Br2 (1-equivalent) would give ;
Br
Br Br Br
Br Br Br
(A) (B) (C) (D)
Br
Ans. (A, B)
18. Which of the following reactions are correct ?
 H Br H
Br2 (i)C6 H5COOH CH2 Cl2
(A) 
CCl4 (B) 
(ii)OH /H O

2
Br H H
Me
Me
(C)
H  /H 2O

 (D) Me
H  /H 2 O
  Me Me H
Me H Me
Me
Ans. (A, B, C)
19. The reagents used to convert (E)-2,3-dibromo-2-butene to 2-butyne
H3C Br
C C  CH3 – C  C – CH3
Br CH3
(A) Zn dust /  (B) Mg,  (C) NaI/ Acetone / (D) Alc. KOH
Ans. (A, B, C)
Misc. Exercise
Subjective
H D
H D
NaOH
1. (A) H 
Alcoholic
 A . Write the structure of A.
D H
Br
CH3
CH3  OH
(B) N 

 B. Write the structure of major product A.
 CH3
2. One of the constituent of turpentine is -pinene havinig molecular formula C10H16. The following scheme give
reaction of  - pinene. Determine the structure of -pinene & of the reaction products A through E.
E(C10H18O2) A(C10H16Br2)
H2O Br2/CCl4
PhCO3H Br2 + H2O
C10 H16 O(D) -pinene B(C10H17OBr)
OsO4 (i) O3 (i) H2SO4
H2O (ii) Me2S (ii) 
F
H C(C10H15Br)
OO
3. Propose structures for intermediates & products A to K
Mg, ether 1.CH3(CH2)3 CHO

1 bromobutane D + E
2. H3O
KOH, H2O H2SO4 , 
A F
O3
1.
Na e 2S Br2
EtBr nPr CHO . M
+ 2
B C G
nBuCHO
fused KOH
followed by NaNH2
H
4. Identify the following (A to D),
Me
E + D + C O + CH3CO2 H
Me
Racemic Mixture
KMnO4 (hot)
C11H20 Lindlar's C11H18 Li/EtNH2 4 ethyl 2, 4 dimethyl

B Catalyst A 2, 5-heptadiene
Optically
active
O3/H2O
Me
+ C O + CH3CO2H
C6H10O4 Me
Optically inactive
C
5. What will be the product in the following reaction
1.NaNH 2 (3equiv.) NH 3
+ Br2 
 A  2.CH 3I
B
6. Write the structural formula of limonene from the following observation :

(A) Limonene when treated with excess H2 & Pt catalyst, the product formed is 1-isopropyl-4-methylcyclohexane
(B) When it is treated with O3 & then Zn/H2O the products of the reaction are HCHO & following compound
O O
7. There are six different alkene A, B,C, D, E and F. Each on addition of one mole of hydrogen gives G which has the
lowest molecular wt hydrocarbon containing only one asymmetric carbon atom. None of the above alkene give
acetone as a product on ozonolysis. Give the structure of A to F. Identify the alkenes that is likely to give a ketone
containing more than five carbon atoms on treatment with a warm conc. solution of alkaline KMnO4.
8. 3,3–dimethyl–1–butene and HI react to give two products, C6H13I. On reaction with alc. KOH one isomer, (I) gives
back 3, 3-dimethyl–1–butene the other (J) gives an alkene, that is reductively ozonized to only Me2C=O. Give the
structures of (I) and (J) and explain the formation of the later.
9. Three isomeric alkenes A, B and C, C5H10 are hydrogenated to yield 2-methylbutane A and B gave the same 3° ROH
on oxymercuration demercuration. B and C give different 1° ROH’s on hydroboration-ixidation. Supply the struc-
tures of A, B & C.
10. Two isomeric alkyl bromides A and B (C5H11Br) yield the following results in the laboratory. A on treatment with
alcoholic KOH gives C and D (C5H10). C on ozonolysis gives formaldehyde and 2 methyl propanal. B on treatment
with alcoholic KOH gives only C (C5H10). Deduce the structures of A, B, C and D. Ignore the possibility of geometri-
cal and optical isomerism.
11. Give the structure of A, B and C.
(A) A (C4H8) which adds on HBr in the presence and in the absence of peroxide to give the same product C4H9Br.
(B) B (C4H8) which when treated with H2SO4/ H2O give (C4H10O) which cannot be resolved into optical isomers.
(C) C (C6H12), an optically active hydrocarbon on catalytic hydrogenation gives an optically inactive compound
C6H14.
12. An alkylhalide, X, of formula C6H13Br on treatment with potassium tertiary butoxide gives two isomeric alkenes Y
and Z (C6H12). Both alkenes on hydrogenation gives 2,3–dimethylbutane predict the structures of X, Y and Z.
13. Compound A (C6H12) is treated with Br2 to form compound B (C6H12Br2). On treating B with alcoholic KOH followed
by NaNH2 the compound C (C6H10) is formed. C on treatment with H2/Pt forms 2-methylpentane. The compound ‘C’
does not react with ammonical Cu2Cl2 or AgNO3. When A is treated with cold KMnO4 solution, a diol D is formed
which gives two acids E and F when heated with KMnO4 solution. Compound E is found to be ethanoic acid.
Deduce the structures from A to F.
14. A organic compound A having carbon and hydrogen, adds one mole of H2 in presence of Pt catalyst to form normal
hexane. On vigrous oxidation with KMnO4, it gives only one simple carboxylic acid containing 3 carbon atoms.
Assign the structure to A.
15. Give the product of
BH3 H 2O 2

THF
 A 
OH 
B
C2H5 C2H5
16. C C 1.CF3 CO 3 H
   A  B . What are A and B ?
2.H O / H 
H H 2
17. What are A to K for the following reactions
(i) PhC  CH + CH3MgX  ArCH2 Cl

 A  Li/NH3
 B  C
h Alcoholic Cold dil. KMnO4 hot KMnO4
(ii) PhCH2CH2CH3 + Br2   D 
KOH
 E(Major)    F  G
H
CH3 l
(iii)   (iv)  
Me Me H3C OH OH
Me
HBr
(v) CF3 – CH = CH2  NBS
 J (vi)  K
Me Me
18. A chloro compound (A) showed the following properties :

(i) Decolourized bromine in CCl4
(ii) Absorbed hydrogen catalytically
(iii) Gave a precipitate with ammonical cuprous chloride
(iv) When vaporised 1.49 g of (A) gave 448 mL of vapours at STP.
Identify (A) and write down the equations of reactions.
Cl
KOH
19. Number of cyclic product(s) formed + HC F
Br
20. It required 0.7 g of a hydrocarbon (A) to react completely with Br2 (2.0 g) and form a non resolvable product. On
treatment of (A) with HBr it yielded monobromo alkane (B). The same compoud (B) was obtained when (A) was
treated with HBr in presence of peroxide. Write down the structural formula of (A) and (B) and explain the reactions
involved. Total dibromoderivative possible for (A) are :
21. Give stability order in the following pairs
I II I II
CH2 CH2
(a) (b)

 
(c) CH 2  N H 2 CH 2  NH 2 (d)
Match the Column

22. Match the column I and II.
Column (I) Column (II)
Reaction Type of Reaction
(A) (p) Meso compound

H2
Ni
CH3
D2
(B) Pt (q) Diastereomers
CH3 CH3
CH2
(C) H2 (r) Racemic

Pt
CH3O
H2
(D) Pt (s) Optically inactive due to absence of chiral center
H H
23. Match the column

Reaction Product
CH3 CH3
D
T
(A) (1) BD3:THF (p)
(2) CH3CO2T
CH3 CH3
D
H
(B) (1) BT3:THF (q)
(2) CH3CO2D
CH3 CH3
H
D
(C) (1) BD3:THF (r)
(2) CH3CO2H
CH3 CH3
T D
(D) (1) BH3:THF (s)
(2) CH3CO2D
24. Match the column.

Wurtz Reaction Number of dimerization product
Na
(A) CH 3 Cl
dry ether (p) 5
Na
(B) CH3 Cl + CH 3 CH2 Cl dry ether (q) 6
CH3 Cl + CH3 CH2 Cl

(C) + CH3 CH2 CH2 Cl Na (r) 3
dry ether
H2C = CH CH= CH CH2 Cl

(D) Na (s) 1
+ CH3 CH2 Cl dry ether
25. Match the column I with column II with column III (Matrix)
Column-I Column-II Column-III
Reaction Nature of product formed Number of chiral center present in product,
(Consider only one isomer in case of racemic
mixture or Diastereomer)
Br2
(A) CCl4 (p) Racemic mixture (w) 0
H
CH3
Br2
(B) CCl4 (q) Meso (x) 1
H
CH3
Br2
(C) CCl4 (r) Diastereomer (y) 2
CH3
CH3 H Br2
(D) C C CCl4 (s) Vicinal dihalide (z) 3
H CH3
26. Match the colum I and II.

Reaction Product
OH
(1) OsO4
(A) (2) NaOH, H2O (p)
(1) BH3/ ether Cl

(B) (2) H2O2, NaOH, H2O (q) OH
OH
Cl2, H2O
(C) (r) OH
Cl
Cl2 / CCl4
(D) (s) Cl
27. Match the column I and II :

Column (I) Columni (II)
Conversion Reagent
CH3
Br
(A) Br (p) SO2Cl2/ h (2 equivalent)
CH3 CH2-Cl
(B) Cl (q) NBS (2 equivalent)
CH3 Br
Cl
(C) (r) NBS then SO2Cl2/ h
CH3 CH2-Cl
Br
(D) (s)SO2Cl2/ h then NBS
28. Match the column I with Column II

Column I Column II
electrolysis
(A) RCOONa   R–R (P) Correy - House reaction
NaOH,CaO
(B) R – CH2 –COOH 
 R – CH3 (Q) Kolbe electrolysis
(i )AgNO3
(C) RCOOH 
(ii)Cl2 / 
 R  Cl (R) Oakwood degradation / Soda lime process
(D) R’ – X + R2CuLi  R–R’ (S) Hunsdiecker reaction
29. Match the column I with Column II

Column I Column II
(i)BH 3 / THF
(A) CH3 C CH2 
(ii)H 2O 2 /OH
 (P) CH3 – CH2 – CH = CH2
CH3
(i)Hg(OAc) 2 /HOH
(B) CH3 C CH2 
(ii) NaBH 4
 (Q) CH3 – CH = CH – CH3
CH3
Cl
CH3ONa/
(C) CH3 CH2 CH CH3   (R) CH3 CH CH2OH
CH3
Cl OH
(CH3 )3 CONa
(D) CH3 CH2 CH CH3  
 (S) CH3 C CH3
CH3
Comprehension
Paragraph (30 to 32)
4-Isomeric alkenes P, Q, R, S with molecular formula C4H8 has following heat of combution data
Head of Combination
S
Q
P R
30. Identify alkene give meso product on reaction with Br2/CCl4 ?

(A) P (B) Q (C) R (D) S
31. Identify alkene give fastest reaction with HBr / CCl4 ?
(A) P (B) Q (C) R (D) S
32. Identify alkene give racemic mixture on reaction with Br2/CCl4 ?
(A) Q (B) R (C) P (D) All of these

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FINAL TOUCH

Single Choice Exercise

2. Double bond equivalent of cubane is

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

Product of the above reaction will be

Br2/h Br2/h Br2/h

7. Select the chain propagation steps in the free-radical chlorination of methane.

(3) Cl  CH 4  CH 3  HCl (4) H + Cl2  HCl + Cl

Br2/h Monobromo derivatives

The number of possible monobromo products is (excluding stereoisomers) :

CH3 CH CH3 H /Pt

Product of the above reaction will be :

(A) (B) (C)

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

(A) 10 (B) 2 (C) 3 (D) 4

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

CH3 CH3 CH3 CH3

Product A of the above reaction is :

CH3 CH3 CH3 CH3

CH3 CH3 CH3

CH3 CH3 CH3

29. Choose the correct product of the following reactions :

(A) CH3 (B) OH

(A) H2 (B) (CH3)2S O3 (C) . Unknown (C) is :

(D) None of these

Product (C) of the above reaction is :

To achieve above conversion, the regents used will be :

CH = CH2 CH = CH2 CH = CH2 CH = CH2

NO2 OH CH3 NH2

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

37. Br2 Stereochemistry of the product is :

Product (A) of the reaction is :

(C) (D) None of these

Give the structural formula of compound (B) :

(D) CH3 – CH2 – C  C – CH2

CH2 CH2 CH3

46. ; This conversion can be achieved by :

(A) NaNH2, CH3CHO (B) NaNH2, CH3 – CH2 – CH2 – Br

(C) KOH, CH3 – CH2 – Br (D) KOH, CH 2 CH2

1.Na, NH3 (liq.)

Compound (X) will be :

(A) CH CH C CH (B) CH CH2 C CH

(C) CH CH2 C CH (D) C CH C CH

CHCH 3 C(CH 3)2

(C) Both correct (D) None is correct

Alkene (P) & (Q) respectively are

(A) Both CH2OH (B) Both CH3

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

(A) Br – CH2–CH=CH–CH2–CCl3 (B) CH 2 CH CH CH 2 CCl3

(C) CH2 CH CH CH2 Br (D) None is correct

(A) + HCHO (B) CH O

58. ( reagent R 2 Reagent R1

R1 and R2 respectively are –

60. Identify (P) in the following reaction :

(A) CH3 – CH2 – C  CH and CH2 = CH – CH = CH2;

(B) CH3 – C  C – CH3 and CH3 – CH = C = CH2 ; CH3 – C  C – CH3

HgSO4 (1)NH3  HCN

(A) Glycine (B) Alanine (C) Valine (D) Leucine

F (CH2)7 H2C CH2 (CH2)6 COOH

68. The compound ‘X’ OH can be synthesized by using the reagents.

(A) – I effect of halogens (B) + I effect of halogens

(A) CH3Cl (B) CH2Cl2 (C) CHCl3 (D) CCl4

76. The major product formed in the following reaction is