LEVEL - IV
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
CH3 CH3
COOH COOH
Br Br Br Br
OH OH
H
H Br Br
and
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
excess H2
1
H 116.2 kcal mol
Ni
++
O
(A)H (B)
3C N
O
H3C C
(C) (D)
N
+
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
(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
(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?
(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) 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 NH2 H C C OH (B) H C C CH3 CH2 NH2 OH
(C) OH NH2 H C C CH3 CH2 (D) NH2 H C C OH CH3 CH2
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
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
N O
(A) N (B) (C) (D)
H
CH 3
3. Tautomerism is exhibited by.
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
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
O
(A) CH CH CH 2 (B) (C) (D)
CH 3 C CH 2
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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(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
C C C C
(A) (p)Polar molecule
H F
F H
C C C
(B) (q)Optically active
H F
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
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
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
R1 R2
6. How many of the following pairs, first intermediate is more stable than the second one?
(7) (8)
(9)
7. How many optical isomers are possible for the following compound ?
KEY
LEVEL - IV
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
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
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
1. A 2. C
HINTS
SINGLE CORRECT ANSWER
O CH3
O
v) H3C O CH3 vi) H3C CH3 vii)
CH3
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
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