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JEE ADVANCED - VOL - IV GENERAL ORGANIC CHEMISTRY

LEVEL - IV

SINGLE CORRECT ANSWER TYPE


I) STRUCTURAL ISOMERISM :

1. All possible structural isomers of the compound with molecular formula C4H10O of following:
(A) 7 (B) 10 (C) 13 (D) 6
2. Functional isomer of ester is :
(A) carboxylic acid (B) anhydride (C) aldehyde (D) ketone
3. C7 H9 N has how many isomeric forms that contain a benzene ring
(A) 4 (B) 5 (C) 6 (D) 7
4. An organic compound has molecular formula C9 H18 . Its all carbon atoms are sp 3 hybridized and
its all hydrogen atoms are identical. Its structural formula can be

(A) CH 3  CH 2  CH  CH  CH 2  CH 3 (B) CH3 CH3


C C
CH CH3 CH3
| C
CH 2 CH3 CH3
|
CH 3

CH3 CH3

(C) CH3 (D)


CH3
CH3 CH3
CH3 CH3
5. Which compound is not isomer of 3-Ethyl-2-methylpentane

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

6. Which of the following is not an isomer of CH 3  CH 2 CHO


O OH

(A) CH  CH  C  CH (B) (C) (D) CH 2  CH  CH 2  OH


3 2 3 O

II) KETO- ENOL TAUTOMERISM :


7. Maximum enolisation takes place in
(A) CH3COCH3 (B) CH2COCH2CHO

(C) CH3COCH2COCH3 (D) O

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8. Tautomerism is not exhibited by


O
N OH
O
(A) O O (B) (C) (D) O
O

9. Tautomerism is not shown by


(A)CH3COCH2CN (B) HCN (C) CH3CH = NOH (D) HCHO
10. HCN and HNC are ....isomers
(A)metamerism (B)tautomers (C)chain (D)position
11. keto-enol tautomerism is observed in
O CH 3
O O O
C 6H 5 C C C 6H 5
(A) (B) (C) (D)
C6H 5 C H C6H5 C CH3 C6H5 C C6H5 CH 3
12. Tautomerism will be exhibited by
(A)  CH 3 2 NH (B)  CH 3 3 CNO (C) R3CNO2 (D) RCH 2 NO2
13. Which among the following compounds will give maximum enol content in solution
O O
O O
(A) C6 H 5  C  CH 2  C  CH 3 (B)
CH 3  C  CH 2  C  CH 3
O O
(C) (D)
CH 3  C  CH 2  CH 2  CH 3 CH 3  C  CH 2  COOC2 H 5

III) GEOMETRICAL ISOMERISM :

14. Which of the following compounds will show geometrical isomerism?


(A) 2-butene (B) propene (C)1-phenylpropene (D)2-methyl-2-butene
15. The geometrical isomerism is shown by:
CH 2 CHCl
CH2 CHCl

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


Me Me Me Me
16. Which will form geometrical isomers?
Cl

(A) (B) CH3CH=NOH (C) (D) All


Cl
17. How many geometrical isomers of CH3CH = CH – CH = NOH exist?
(A)Five (B)Two (C)Three (D)Four
18. Geometrical isomerism is possible in:
(A) Pentene-2 (B) Ethene (C) Propane (D) Propene

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19. Which will show geometrical isomerism

COOH COOH
Br Br Br Br
OH OH

H
H Br Br

(i) (ii) (iii) (iv)


(A) i, ii, iii, iv (B) i, ii, iii (C) i, iii, iv (D) ii, iii, iv
20. The number of geometrical isomer for CH 3  CH  CH  CH  CH  CH  CH 2
(A) 2 (B) 4 (C) 6 (D) 8
IV) OPTICAL ISOMERISIM :
21. How many stereoisomers are possible for the following molecule?
Cl
Br

(A) 4 (B) 8 (C) 12 (D)16


Cl
22. Number of chiral carbon atoms in is
(A) 2 (B) 3 (C) 4 (D) 1
23. Number of optical active isomers of tartaric acid is
(A) 2 (B) 3 (C) 5 (D) 6
CH3 CH CH CH CH3
24. The number of optically active isomers possible for | |
OH OH OH
| is
(A) 2 (B) 3 (C) 6 (D) 8
V) CONFORMATIONAL ISOMERISM :
25. Most stable form of cyclohexane is
(A) boat (B) chair (C) skew (D) eclipsed
26. What are the type of isomers in following pairs?

and

(A)Conformers (B) position (C)Optical (D) Geometrical

27. Which type of conformation is shown by I and II?


H H
H H
H

H H
H H H
H H
(I) (II)
(A)I is eclipsed, II is staggered (B) II is eclipsed, I is staggered
(C) both are eclipsed (D) both are staggered
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28.  The most stable conformational isomer of cis-1-bromo-2-chlorocyclohexane will have...
(A) both halide atoms in axial positions. (B) both halide atoms in equatorial positions.
(C) the bromine atom in an axial position and the chlorine atom in an equatorial position
(D) the bromine atom in an equatorial position and the chlorine atom in an axial position.
29. The most stable conformation of 3-fluorobutan-2-ol is
A) Fully eclipsed form B) Partially eclipsed form C) Gauche form D) Anti form
30. In the newman projection formula of most stable conformation of 3-Hydroxypropanal is stable
due to
A) Minimum torsional strain B) Intramolecualr hydrogen bonding
C) Minimum torisonal strain and intera molecular hydrogen bonding D) Minimum steric strain
31. In the given conformation C2 is rotated about C 2  C3 bond anticlockwise by an angle of 120°
then the conformation obtained is
CH 3
H H

H H

CH3
A) Fully eclipsed conformation B) Partially eclipsed conformation
C) Gauche conformation D) Staggered conformation
32. The dihedral angle between two methyl groups in partially eclipsed conformation of n-butane
is
A) 180° B) 120° C) 90° D) 109° 281
33. In the Newmann projection formula of the least stable staggered form of n-butane. Which of
the following reasons is the causes of its unstability
A) Vander-Waal’s strain B) Torsional strain C) Combination of both D) None of these
34. The identical compounds are
D
H
Cl H
D Cl
H D H D

X) Y) Z) W)
H Cl D Cl
H H D
H
Cl Cl D D Cl
Cl

A) X,Y B) Y,Z C) Y,W *D) X,Z


VI) ELECTRONIC EFFECTS-INDUCTIVE,MESOMERIC EFFECTS AND
HYPERCONJUGATION:
35. Which of the following statements about hyperconjugation is not correct?
(A)Hyperconjugation requires proper alignment of the participating bond with the system (or p orbital)
(B) Hyperconjugation in propene leads to an increase in the electron density on the terminal carbon of the
double bonde (as compared to ethene)
(C) Hyperconjugation results in deloclization of electron density from a single bond into a p system (or a p
orbital)
(D) The strength of hyper conjugation increases with the increased electronegativity of the atom forming
the participating s bond
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36. The –I effect of –NO2, –CN, –COOH, –Cl, decreases in the order
(A) –NO2 > –CN > –COOH > –Cl (B) –Cl > –COOH > –CN > –NO2
(C) –CN > –NO2 > –Cl ? –COOH (D) –COOH > –CN > –NO2 > –Cl
37. Which statement is correct for inductive effect?
(A) it is a permanent effect (B) it is the property of bond
(C) it causes permanenet polarization in the molecule (D) all are correct
38. Hyperconjugation phenomenon is possible in
CH3
|
CH 3  C  CH  CH 2
A) | B) CH 2  CH 2
CH 3
C) C6 H 5  CH  CH 2 D) CH 3  CH 2  CH  CH 2
39. Which of the following molecule has longest C  C bond length?
CH3
| CH 3  C  CH 2
CH 3  C  CH  CH 2 |
A) CH 2  C  CH 2 B) CH 3  CH  CH 2 C) | D) CH3
CH 3
VII) RESONANCE :
40.  A Lewis formula for diazomethane, CH2N2, is shown on the left below.
Which of the formulas within the brackets would be considered a proper resonance contributor
to this structure ?

41. Use the following data to answer the question below:


H2
1
H  28.6 kcal mol
Ni

excess H2
1
H  116.2 kcal mol
Ni

Calculate the resonance energy of anthracene


(A)84 kcal/mol (B)100 kcal/mol (C)110 kcal/mol (D)116 kcal/mol
42. Which of the following structure is the most stable?

++
O
(A)H (B)
3C N
O
H3C C
(C) (D)
N

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43. The least stable resonating structure is

A) 
B)
O O
 
C) O D)
 O 
44. Which of the following pairs of structures is not a pair of resonating structures?
  
A) H  C  N H; H  C  N H B) CH 3CH  CHCH 3 ; CH 3CH 2 CH  CH 2

 +
CH 3  C  CH  C  CH 3 ;CH 3  C  C H  C  CH 3
| || || ||
C) O O O O D)
+
45. Which of the following is not a permissible resonating form.

       
C H2  N O CH 2  N  O CH 2  N  O CH 2  N  O
A) | B) | C) | D) |
CH 3 CH 3 CH3 CH 3
46. The C  Cl bond length is shortest in
(A) CH 2  CH  Cl (B) CH 3  Cl
(C) C6 H 5  CH 2  Cl (D) CH 2  CH  CH 2  Cl
VIII) REACTION INTERMEDIATES - CARBOCATIONS, CARBANIONS & FREE RADICALS
47. Which one among the following carbocations has the longest life span?

Me
+ + +
C + C Me
(A) (B) C (C) C (D)
Me

48. The compound which gives the most stable carbonium ion on dehydration is:
CH3
CH3 CH CH2OH CH3 C OH CH3 CH CH2 CH3
(A) CH3
(B) (C) CH3 - CH2 - CH2 - CH2OH (D)
OH
CH3

49. The correct stability order for the following species is


+ + +
O O +
(I) (II) (III) (IV)

(A) (II) > (IV) > (I) > (III) (B) (I) > (II) > (III) > (IV)
(C) (II) > (I) > (IV) > (III) (D) (I) > (III) > (II) > (IV)
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50. Some pairs of ions are given below, in which pair, first ion is more stable than second?
 
(A) CH  C H  CH and CH  C H  OCH
3 3 3 3
 
(B) CH 3  CH 2  C H  CH 3 and CH 2  CH  CH 2  C H 2

+ + H3C CH CH3 H3C N CH3


CH2 CH2 and
(C) and (D) H3C C CH3 H3C C CH3
+ +

51. Which one of the following carbocation is not formed easily?

(A) (C6H5)3C+ (B) (C) (D) CH2 = CH – CH2+

52. Which of the following is the most stable?


+ + + +
(A) Ph3 C (B) Ph 2 C H (C) Ph 3CC H 2 (D) Ph C H 2
53. A free radical is
(A) neutral in character (B) shortly lived (C) paramagnetic (D) all the above
54. The order of decreasing stability of the carbanions
..  ..  ..  .. 
(1) (CH 3 )3 C (2) (CH ) C H (3) CH 3 C H 2 (4) C6 H 5 C H 2
3 2

(A) 1 > 2 > 3 > 4 (B) 4 > 3 > 2> 1 (C) 4 > 1 > 2 > 3 (D) 1 > 2 > 4 > 3
55. What is the decreasing order of stability of the ions?

H3C HC H3C HC H3C HC


CH3 O CH3 CH3
O
(I) (II) (III)

(A) I > II > III (B) II > III > I (C) III > I > II (D) II > I > III
+
56. An electrophile, E , attacks the benzene ring to generate the intermediate  -complex. Which of
the following s-complex is of lowest energy?
NO 2 NO 2
H NO 2 H

(A) + (B) (C) (D) + H


+ E + E
H E E

IX) ACIDITY OF ORGANIC ACIDS:

57. Acidic nature of HO Xis increased if X is:

(A)— NO2 (B)— CH3 (C)— OCH3 (D) NH 2


58. Which of the following has the most acidic hydrogen ?
(A) 3-hexanone (B) 2, 4-hexanedione (C) 2, 5-hexanedione (D) 2, 3-hexanedione.

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59. Which is an acidic hydrocarbon
(A) CH3CH2CH2CH3 (B) CH 3C  CCH 3
(C) CH 3C  CH (D) CH2 = CH – CH = CH2
60. Arrange given compounds in order of decreasing acidity:
NO 2

(1)CH3—NO2 (2)NO2–CH2–NO2 (3)CH3—CH2—NO2 (4)O2N


NO 2
(A) 4 > 2 > 1 > 3 (B) 4 > 2 > 3 > 1 (C) 3 > 1 > 2 > 4 (D) 3 > 1 > 4 > 2.
61. Phenol, p-Methylphenol, m-Nitrophenol and p-Nitrophenol follows order of increasing acidic
strength
(A) Phenol, p-Methylphenol, p-Nitrophenol, m-Nitrophenol
(B) p-Methylphenol, Phenol, m-Nitrophenol, p-Nitrophenol
(C) p-Methylphenol, m-Nitrophenol, Phenol, p-Nitrophenol
(D) m-Nitrophenol, p-Nitrophenol, Phenol, p-Methylphenol
62. Which of the following is the strongest acid ?
OH
OH
(A) (B) Cl OH (C) (D) O 2N OH
NO2 NO 2
63. In the follwing compounds, the order of acidic strength is
OCH 3 O 2N

(I) OH (II) H3CO OH


(III) OH (IV) O2N OH

(A) III > IV > I > II (B)I > IV > III > II (C) II > I > III > IV (D) IV > III> I > II
64. Which of the following facts explain as to why p-nitrophenol is more acidic than phenol ?
I) -I effect of nitro group
II) Greater resonance effect of p-nitrophenoxy group
III) Steric effect of bulky nitro group
Select the correct answer using the codes gives below :
(A) II and III (B) I and III (C) I and II (D) II alone\
X) BASICITY OF ORGANIC BASES :
65. What is the decreasing order of strength of the bases and
(A) CH3  CH2  NH2  H  C  C   OH (B) H  C  C   CH3  CH2  NH2  OH
(C) OH  NH2  H  C  C   CH3  CH2 (D) NH2  H  C  C   OH  CH3  CH2
66. Which is the strongest base among the following?
(A)Ph – NH2 (B)Ph – NH – – CH3 (C)Ph – CH2 – NH2 (D)Ph – NH – Ph
NH 2 NH 2
NH 2

67. I) II) III)

CH 3 NO 2
Correct order of basic strength is
A) II > I > III B) I > II > III C) III > II > I D) II > III > I

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68. Choose the strongest base among the following
A) C6 H 5 CONHCH 3 B) C6 H 5 NH 2 C) C6 H 5  CO  NH 2 D) C6 H 5  NH  CH 3
69. Choose the strongest base among the following
A) C6 H 5 NH 2 B) p  NO 2  C 6 H 4 NH 2
C) m  NO2  C 6 H 4 NH 2 D) C6 H 5 CH 2 NH 2

MORE THAN ONE ANSWER TYPE

1. Only two isomeric monochloro derivatives are possible for


(A) n-butane (B) 2, 4-dimethylpentane (C) benzene (D) 2-methylpropane
2. Which can not exhibit tautomerism here
O

N O
(A) N (B) (C) (D)

H
CH 3
3. Tautomerism is exhibited by.

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

4. Which have active methylene group?


O
O O O

(A) (B)H3C NO 2 (C) CN (D)


H3C CH3 H3C
NC
5. Which of the following exhibit geometrical isomerism (Cis-trans)
H
Cl
H Cl

Cl Cl
(A) (B) CH 3CH  CCl2 (C) (D)
Br Br
C
H Cl
H Cl
6. Which of the following cycloalkanes will show cis-trans isomerism?
CH 3
CH 3 H 3C
CH 3 CH 3
(A) (B) CH 3 (C) (D)
H 3C
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7. Which will show geometrical isomerism?
H3C
H3C N HO N
(A) N OH
(B) (C) (D) N OH
H3C OH

8. Which of the following have asymmetric carbon atom?


Cl Br H Cl H Cl H Cl
(A)F C C H (B) H–C–C–Cl (C) H–C–C–H (D) H–C–C–CH 3

H H H H H H Br OH
9. Identify the correct statement (s) about diastereomers?
(A)Diastereomers differ in their solubility and melting point
(B)Diastereomers have same specific rotation
(C)Diastereomers can not be separated by fractional distillation.
(D)Diastereomers are the stereoisomers which are not mirror images
10. Select the correct statement
A) A racemic mixture can be distinguished from a meso or an achiral compound by optical resolution
B) d and l stereoisomer of the same compound are enantiomer
C) A chiral compound may or may not have assymetric carbon
D) There is no obvious correlation that exists between the configurations (R or S) of enantiomers and the
direction    or     in which they rotate plane polarised light

F F C 2 H5
H3 C H H 5 C2 H H OH

11. H5 C 2 OH H 3C H F H

H OH CH 3
(I) (II) (III)
Incorrect relation between above compounds
A) I & II are structural isomers B) I & III are Diastereomers
C) I & II are enantiomers D) II & III are enantiomers
12. Which of the following pairs of compounds are diasteriomers?
CH3 CH3 CH3 CH3
H OH H OH HO H HO H
and and
(A)HO H H OH (B) H OH HO H
CH3 CH3 CH3 CH3

CH3 CH3 CH3 CH3


H OH HO H H OH HO H
and and
(C)HO H H OH (D)HO H HO H
CH3 CH3 CH3 CH3

13. Which of the following compounds is/are optically inactive


(A) (CH3)2 CHCH2OH (B) CH3CH2OH
(C) CCl2F2 (D) CH3CH(OH)C2H5

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COOCH3 CH3 OCOCH3


H H3C H H CH3
CH3

H CH3 H3C COOCH3 CH3 CH3


14.
CH3 H H

(I) (II) (III)

Correct relation between above compounds


A) I & II are position isomers B) I & II are chain isomers
C) II & III are metamers D) II & III are identical
15. Which of the following compounds cannot show hyperconjugation?
O
CH 3 CH 3
CH
CH 3 CX 3
C  CH 3
(A) (B) (C) (D)
CH 3
O
16. Which of the following group (s) exerts +I effect?
(A) CO2 (B) CH3 (C) NH3 (D)OH
17. Identify the correct statment (s) about inductive effect?
(A) it is permanent
(B) it increases as the distance from the source increases
(C) it is the property of bond
(D) it implies the transfer of lone pair of electrons from lesser electronegative atom to the more electronegative
atom
18. Resonance structures of a molecule should have
(A) Identical arrangments of atoms (B) Nearly the same energy content
(C) The same number of paired electrons (D) Identical bonding
19. Which of the following statements is/are correct?
A) The energy of hybrid structure is always less than that of any resonating structure
B) The resonance energy is the difference between the enthalpies of formation of the molecule and the
resonating structure having maximum energy
C) Kekule’s structures have larger contribution than Dewar’s structure in the hybrid structure of benzene
D) In delocalized structure of benzene the  -charge cloud is spread equally above and below the plane of
molecule
20. During resonance, which is/are correct?
A) Net charge remains same B) Number of paired electron remains same
C) Number of unpaired electron remains same
D) Energy of resonating structures always remains same
21. The resonating structures of a molecule should have
(A) Identical arrangement of atoms (B) Nearly the same energy content
(C) The same number of paired electrons (D) Identical bonding
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22. The heterolytic cleavage of R-Cl bond gives alkyl carbonium ion R+. Which of the following
statements about carbonium ion is (are) true?
(A)the carbonium ion is generally planar in shape
(B)the carbonium ion contains generally carbon in tetrahedral state
(C)the carbon in carbonium ion has an incomplete octet
(D)presence of electron pushing groups increases the stability of carbo cations

23. Among following anions which are more stable than CH 2 ?

O
(A) CH CH CH 2 (B) (C) (D)
CH 3 C CH 2

24. Which of the following are nucleophiles?


(A) CN    (B) BF3 (C) R  O  R (D) NH 3
25. Among the following which compound is / are having lower pKa value than benzoic acid?
(A) HCO2H (B)Picric acid (2, 4, 6 trinitro phenol)
(C)CH3CO2H (D)O-nitrophenol
26. Which is/are less acidic than phenol?

OH OH
(A)CH3OH (B) (C) (D) H2O
CH3 NO 2

27. Among the following which compound is / are having lower pKa value than benzoic acid?
(A) HCO2H (B) Picric acid (C) CH3CO2H (D) o-nitrophenol
28. Phenol is less acidic than
(A) Acetic acid (B) p-methoxyphenol (C) p-nitrophenol (D) ethanol
29. Mention the following compounds, which is / are more acidic than H2O
(A) HC  CH (B)HF (C)Phenol (D) CH3 – CH2 – OH
30. Which of the is arranged correctly for decreasing K a order
A) CH 4 , NH 3 , H 2 O, HF B) CH 3  OH, CH3  NH 2 , CH3  F, CH 3  CH 3
C) HI, HBr, HCl, HF D) PhOH, H 2 O, C 2 H5 OH, CH 3  C  CH
31. Which of the following satements regarding aniline is (are) correct?
(A)aniline is a weaker base than ethyl amine
(B)C – N bond in aniline is shorter than that in ethyl amine
(C)anilinium ion C6H5NH3 does not show resonance effect
(D)aniline is a stronger base than NH3
32. Which of the following series of bases shows a left to right increase in basic strength?
(A)NH3, aniline, p-nitro aniline (B)Ph3N, Ph2NH, Aniline
(C)Aniline, NH3, CH3 – NH2 (D) Aniline, NH3,
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COMPREHENSION TYPE QUESTIONS


Comprehension - I
The conversion of a keto form into enol is enolisation. It depends on structural factor, temperature
and nature of solvent. Resonance and hydrogen – bonding increases enol content. Enolic form of
phenol is more stable than keto form by –13 kcal/mol of energy hence phenol exist exclusively
as an enol. Enolic tautomer is less polar due to intramolecular hydrogen bonds than the
corresponding keto form. Any polar solvent would decrease the enolisation and favour keto
form intramolecular hydrogen bonding stabilized enol form by 7kcal/mol and resonance stabilizes
enol form by 15 kcal/mole
1. The enol content of ethyl acetoacetate is highest in
(A) Water (B) acetic acid (C) ethanol (D) hexane
2. Which one of the following compounds has maximum enol content?
(A) CH3COCH2COOCH3 (B) CH3COCH2COOC2H5
(C) CH3COCH2COCH3 (D) C6H5COCH2COC6H5
3. Ketonic form predominates in
(A) CH3 – CO – CH3 (B) C6H5COCH2COCH3
(C) CH3 – CO – CH2 – COCH3 (D) CH3COCH2COOC2H5
Comprehension - II
Carbocations are species in which central carbon carries positive charge. If the charge on the
carbocations gets concentrated or localized the carbocation becomes unstable. The two factors
which account for stability of carbocations are inductive effect and hyper conjugation (no bond
resonance). Inductive effect is minor factor and hyper conjugation is major factor.
4. Which is most stable carbocation?
   
(A) C H3 (B) CH 3 C H 2 (C) (CH 3 )2 C H (D) (CH 3 )3 C
5. n-propyl carbocation rearranges to isopropyl carbocation by shift of
(A) proton (B) Hydride ion (C) electron (D) None of these
6. Hybridisation of carbon in carbocation is
(A) sp (B) sp2 (C) sp3 (D) dsp2
Comprehension - III
CH3 - CH2 - CH = CH2 + CH3OH CH3 - CH - CH2 - CH3
|
OCH3
7. Consider the above reaction and answer A to E.
A. What is electrophile in first step?
 
(a) CH3 (b) H (c) CH3  CH2  CH  CH3 (d) HO
B. What is nucleophile in first step?
(a)CH3OH (b) 1-butene (c) H2O (d) CH3–O–CH3
C. What is electrophile in second step?
  
(a) CH 3
(b) H (c) CH3  CH2  CH  CH3 (d) CH3  CH2  CH2  CH2
D. What is nucleophile in second step?
(a) CH3–CH2–CH=CH2 (b) CH3OH (c) H2O (d) CH3–O–CH3
E. Which step is rate determining step?
(a)attack of nucleophille CH3OH (b)attack of electrophile H

(c)attack of nucleophile H2O (d)attack of electrophile CH3

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Comprehension - IV

(I)

(II)

(III)

8. Which of the following is the most suitable ‘X’ for the stability of I
a) –CH3 b) –OCH3 c) –NO2 d) –CHMe2
9. Which of the following is the most suitable ‘Y’ for the stability if II
a) –CH3 b) –OCH3 c) –NO2 d) –CHMe2
10. Which of the following is the most suitable ‘Z’ for the stability of III
a) –CH3 b) –OCH3 c) –NO2 d) –CHMe2

MATRIX - MATCH TYPE QUESTIONS

1. Match the column I and II (Matrix)


Column-I Column-II
(A) –NO2 (p)–m effect
(B) O  (q)+m effect
(C) –O–CH3 (r)+ I effect
(D)–CN (s)–I effect
2. Match the column I and II
Column-I Column-II
F H

C C C C
(A) (p)Polar molecule
H F
F H

C C C
(B) (q)Optically active
H F

(C)F F (r)Optically inactive


F H

H H
(D) (s)Plane of symmetry
H H
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3. Column – I (Properties) Column – II (Reaction intermediate)
(A)Stability order: 3° > 2° > 1° (p)Methyl carbocation
(B)Stability order: 1° > 2° > 3° (q)Alkyl cabrocation
(C)No hyperconjugation (r)Carbanion
(D)Two unshared pair of electrons (s)Nitrene
4. Match the following
Column-I Column-II
(Isomers) (Type of isomers)
O O
|| ||
A) CH  C CH 2CH 2CH 3 and CH CH 2  C  CH 2 CH 3 p) Functional isomers
3 3
CH 3
| CH 3 CH 3
CH  C  CH 2  CH 3 | |
B) 3 and CH  CH  CH  CH 3 q) Position isomers
| 3
CH
3
CH 3
|
C) CH 3  CH 2CH 2CH 2CHD2 and CH  CH  CHD  CH 2 D r) Metamers
3
D) CH 3 CH 2 CH 2 NH 2 and CH 3CH 2 NHCH 3 s) Chain isomers
ASSERTION - REASONING TYPE

(A)Statement–1 is True, Statement–2 is True; Statement–2 is a correct explanation for Statement– 1.


(B)Statement–1 is True,Statement–2 is True;Statement–2 is NOT a correct explanation for Statement–1
(C)Statement – 1 is True, Statement – 2 is False.
(D)Statement – 1 is False, Statement – 2 is True.

1. STATEMENT–1: Phenol is more reactive than benzene towards electrophilic substitution reaction.
STATEMENT – 2: In electrophilic substitution reactions of phenol, the intermediate carbocation is more
resonance stabilised.
2. STATEMENT – 1: Molecules that are non-superimposable on their mirror image are chiral.
STATEMENT – 2: All chiral molecules have chiral centres.
INTEGER TYPE QUESTIONS
1. Among the following how many of them is/are more acidic than phenol ?
OH COOH OH

HO NO2, HO , H2CO3 , HCO2H, CH3COOH, , ,


NO 2

2. Among the following how many of them will show keto-enol tautomerism?
O O
CH3CHO, , HCHO, CH3COCH3, C
O

CH3CH2CHO, O O, O O

3. How many structural isomers are possible for C6H14?


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4. How many of the following compounds are more acidic than ethyne?
CH2 = CH2, NH3, H2O; CH3 – CH3, HF, CH3CH2–OH, CH3–CH2–SH,
5. How many stereoisomers of the following compound is/are possible?

R1 R2
6. How many of the following pairs, first intermediate is more stable than the second one?

(1) (2) (3)

(4) (5) (6)

(7) (8)

(9)

7. How many optical isomers are possible for the following compound ?

8. How many isomers are possible with the formula C2ClBrFI?


9. How many of the following posses plane of symmetry?

10. How many of the following statements are correct?


1) The most stable conformer of cis-1, 3-cyclohexanediol is chair form.
2) Cis-1, 3- cyclohexanediol is more stable than trans -1, 3- cyclohexanediol.
3) In Cis 1, 3- cyclohexanediol both the OH groups occupy equitorial positions.
4) The most stable conformer of trans -1, 4- cyclohexanediol is chair form.
5)The most stable conformer of cis-1, 4- cyclohexanediol is boat conformer.
11. How many diastereomeric forms are possible for 1, 2, 3 trisubstituted cyclobutane when all the
substituents are identical?
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KEY
LEVEL - IV

SINGLE CORRECT ANSWER TYPE

01. A 02. A 03. B 04. B 05. B 06. A 07. D 08.A


09. D 10. B 11. B 12. D 13. A 14. A 15. D 16. D
17. D 18. A 19. B 20. B 21. D 22.A 23. A 24. A
25. B 26. A 27. B 28. D 29. C 30. C 31. C 32. B
33. A 34. D 35. D 36. A 37. D 38. D 39. D 40. B
41. A 42. B 43. C 44. B 45.C 46.A 47.A 48. B
49. D 50. B 51. C 52. A 53. D 54. B 55. D 56.B
57. A 58.B 59. C 60. A 61. B 62. D 63. D 64. C
65. A 66. C 67. A 68. D 69. D

MULTIPLE CORRECT ANSWER TYPE

01. A,D 02. A,D 03. A,C,D 04. A,B,C,D 05. A,D 06. C,D 07. A,B,D
08. A,D 09. A,C,D 10. A,B,C,D 11. B,C,D 12. A,B,D 13. A,B,C 14. A,C
15. B,C 16. A,B 17. A,C 18. A,B,C 19. A,C,D 20. A,B,C 21. A,B,C 22. A,C,D
23. C,D 24. A,C,D 25. C,D 26. A,B,D 27. A,B 28. A,C 29. B,C 30. B,C,D
31. A,B,C 32. B,C

COMPREHENSION TYPE QUESTIONS

1. A 2. D 3. A 4. D 5. B 6. B
7. A – b; B – b; C – c; D – b; E–b 8. D 9. B 10. C

MATRIX - MATCH TYPE QUESTIONS

1. A – p, s; B – q, r; C – q, s; D – p, s;
2. A – r,s; B – p, q; C – r, s; D – p, r, s;
3. A – q; B – r; C – p; D – s;
4. A – q,r; B – s; C – q,s; D–p

ASSERTION - REASONING TYPE QUESTIONS

1. A 2. C

INTEGER TYPE QUESTIONS

1. (6) 2. (5) 3. (5) 4. (4) 5. (8) 6. (4) 7. (8) 8. (6)


9. (4) 10. (4) 11. (3)

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HINTS
SINGLE CORRECT ANSWER

1. (A)Total number of structural isomers = 7


CH3
CH3 OH
iv) H3C OH
i) H3C OH ii) OH iii)
H3C CH3

O CH3
O
v) H3C O CH3 vi) H3C CH3 vii)
CH3

2. Carboxylic acid is the functional isomer of an ester


OH

7. is stabilized by resonance.

9. No acidic  - hydrogen
11. For a compound to exhibit keto- enol isomerism, presence of  - hydrogen is necessary. This is satisfied
only by acetophenone
12. A,B,C doesnot contain acidic  - hydrogen
13. ‘A’ has strongest active methylene group.
17. Two stereo centers  No.of Geometrical isomers  2n

20. Two stereo centers  No.of Geometrical isomers  2n

21. Four stereo centers  No.of stereo isomers  24


22. The given structure has two chiral centers.
23. Tartaric acid has two optically active isomers and one meso form.
24. The given structure has two optically active isomers and one meso form.
29. Gauche conformation is most stable due to intramolecular hydrogen bonding.
31. When the anti conforrmer is rotated by 1200 gauche conformer is resulted.
33. Fully eclipsed conformation of n-butane is unstable due to vanderwaal’s strain.
34. Dihedral angle between DCCl of front and rear carbons is same in X & Z .
35. To show hyper conjugation an , an α - carbon having atleast one α-H attached to an sP 2 hybridised ‘C’
is necessary.
36. Resonance energy  28.6  7 116.2
= 84. Kcal / Mol

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38. Carbon - carbon double bond acquires some single bond character due to no bond resonance.
45. In ‘C’ around ‘N’ five bonds ara present.
46. Due to resonance in A.
47. ‘A’ is most stable.
48. 30 carbocation is most stable given by B.
51. Bridged head carbocation is highly unstable.
52. Ph3 C + is most stable due to resonance
57. e  withdrawing by inductive and mesomeric effectc increases the acdic strength.
58. 2,4 - hexane dione has strong active metyylene group.
59. ‘H’ attached to triple bonded ‘C’ is acdic in nature.
65. Conjigate acids strength order is CH 3 -CH 3 < NH 3 < H- C  C - H < H 2O
66. The l.p present ‘N’ is not involed in delocalisation in ‘C’

MORETHAN ONE CORRECT ANSWER

4. A has active methylene group due to the presence of strong  I groups


12. B and D contains pair of non - mirror images.
13. A,B,C does not contain a chiral center.
23. Carbanion is stabilized by electron withdrawing groups by inductive and mesomeric effects
25. Acetic acid and O  nitrophenol are stronger acids than benzoic acid.
26. The presence of e- donating groups by inductive and mesomeric effects decreases acidic nature of
phenol.
27. HCOOH and picric acids are stronger than benzoic acid.

ASSERTION & REASONING TYPE

1. –OH group is electron donating group, thus activates the benzene ring for electrophilic substituion reaction.
Due to more resonance stabilisation of phenoxide ion, it gives more stable carbocation (intermediate).
2. Molecules having perpendicular dissymmetric plane are supposed to have chirality without having chiral
centre.

NO2 COOH

H3C H
e.g., C=C=C
H3C CH3
HOOC NO2

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