GOC

JEE MAINS
1. In the following benzyl/allyl system R – CH = CH2 and (R is alkyl group)

Then decreasing order of inductive effect is : [AIEEE-2002]

(1) (CH3)3 C— > (CH3)2CH— > CH3CH2— (2) CH3CH2— > (CH3)2CH— > (CH3)3C—
(3) (CH3)2CH— > CH3CH2— > (CH3)3C— (4) (CH3)3C— > CH3CH2— > (CH3)2CH—
Ans. (1)
2. Picric acid is - [AIEEE - 2002]

COOH COOH OH COOH

NO2 NO2
(1) (2) (3) (4)
NO2 OH NH2
NO2

Ans. (3)
3. Which of the following species acts both as bronsted acid & base – [AIEEE - 2002]

(1) NH3 (2) OH– (3) HSO 4 (4) 1 and 3 both

Ans. (4)
4. The correct order of increasing basic nature for the bases NH3, CH2NH2 and (CH3)2NH is – [AIEEE - 2003]
(1) CH3NH2 < NH3 < (CH3)2NH (2) (CH3)2NH < NH3 < CH3NH2
(3) NH3 < CH3NH2 < (CH3)2NH (4) CH3NH2 < (CH3)2NH < NH3
Ans. (3)

5. In the anion HCOO– the two carbon-oxygen bonds are found to be of equal length. What is the reason for it -
[AIEEE - 2003]
(1) Electronic orbits of carbon atoms are hybridised
(2) The C = O bond is weaker then the C – O bond.
(3) The anion HCOO– has two resonating structure.
(4) The anion is obtained by removal of a proton from the acid molecule.
Ans. (3)
6. Which one of the following does not have sp2 hybridised carbon [AIEEE - 2004]
(1) Acetamide (2) Acetic acid (3) Acetonitrile (4) Acetone
Ans. (3)
7. Consider the acidity of the carboxylic acids [AIEEE - 2004]
(i) PhCOOH (ii) o–NO2C6H4COOH
(iii) p–NO2C6H4COOH (iv) m–NO2C6H4COOH
(1) i > ii > iii > iv (2) ii > iv > iii > i (3) ii > iv > i > iii (4) ii > iii > iv > i
Ans. (4)

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8. Which of the following is the strongest base - [AIEEE - 2004]

(1) NH2 (2) NHCH3 (3) NH 2 (4) CH2NH2

CH 3

Ans. (4)
9. Due to the presence of an unpaired electron, free radical are - [AIEEE - 2005]
(1) Chemically inactive (2) Chemically reactive (3) Cations (4) Anions
Ans. (2)
10. What is the conjugate base of OH– ? [AIEEE - 2005]
(1) H2O (2) O2 (3) O2– (4) O –

Ans. (3)
11. The correct order of increasing acid strength of the compound is [AIEEE - 2006]
Me
(a) CH3CO2H (b) MeOCH2CO2H (c) CF3CO2H (d) CO 2H
Me
(1) d < a < c < b (2) d < a < b < c (3) a < d < c < b (4) b < d < a < c
Ans. (2)
12. The increasing order of stability of the following free radicals is : [AIEEE-2006]
• • • •
(1) (C6H5)3 C < (C6H5)2 CH < (CH3)3 C < (CH3)2 CH
• • • •
(2) (C6H5)2 CH < (C6H5)3 C < (CH3)3 C < (CH3)2 CH
• • • •
(3) (CH3)2 CH < (CH3)3 C < (C6H5)3 C < (C6H5)2 CH
• • • •
(4) (CH3)2 CH < (CH3)3 C < (C6H5)2 CH < (C6H5)3 C
Ans. (4)
13. Which one of the following is the strongest base in aqueous solution ? [AIEEE - 2007]
(1) Trimethylamine (2) Aniline (3) Dimethylamine (4) Methylamine
Ans. (3)

14. Arrange the carbanions, (CH3)3 C , CCl3 , (CH3)2 CH, C6H5 CH 2 in order of their decreasing stability : [AIEEE-2009]

(1) (CH3)2 C H > C Cl3 > C6H5 C H2 > (CH3)3 C (2) C Cl3 > C6H5 C H2 > (CH3)2 C H > (CH3)3 C

(3) (CH3)3 C > (CH3)2 CH > C6H5 C H2 > C Cl3 (4) C6H5 CH2 > CCl3 > (CH3)3 C > (CH3)2 CH
Ans. (2)
15. The correct order of increasing basicity of the given conjugate base (R = CH3) is :- [AIEEE - 2010]
(1) RCOO– < HC  C– < NH2– < R– (2) RCOO– < HC  C– < R– <NH2–
(3) R– < HC  C– < RCOO– < NH2– (4) RCOO– <NH2– < HC  C– < R–
Ans. (1)
16. The strongest acid amongst the following compounds is ? [AIEEE - 2011]
(1) CH3CH2CH(Cl)CO2H (2) ClCH2CH2CH2COOH (3) CH3COOH (4) HCOOH
Ans. (1)
17. The correct order of acid strength of the following compounds :- [AIEEE - 2011]
A. Phenol B. p-Cresol C. m-Nitrophenol D. p-Nitrophenol
is :
(1) C > B > A > D (2) D > C > A > B (3) B > D > A > C (4) A > B > D > C
Ans. (2)

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18. The non aromatic compound among the following is [AIEEE - 2011]

(1) (2) (3) (4)

S
Ans. (1)

19. Identify the compound that exhibits tautomerism. [AIEEE-2011]

(1) 2-Butene (2) Lactic acid (3) 2-Pentanone (4) Phenol
Ans. (3)
20. In the following compounds : [JEE (Main) - 2012]

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

N N
N
N
H H
H

the order of basicity is as follows :

(1) IV > III > II > I (2) II > III > I > I > IV (3) I > III > II > IV (4) III > I > II > IV
21. The most basic compound among the following is :- [JEE (Main) - 2012]
(1) Acetanilide (2) Benzylamine (3) p-Nitro aniline (4) Aniline
Ans. (3)
22. ortho-Nitrophenol is less soluble in water than p– and m– Nitrophenol because : [AIEEE - 2012]
(1) Melting point of o-Nitrophenol is lower than those of m– and p– isomers.
(2) o-Nitrophenol is more volatile in steam than those of m– and p– isomers.
(3) o-Nitrophenol shows Intramolecular H – bonding.
(4) o-Nitrophenol shows Intermolecular H – bonding.
Ans. (3)
23. Which of the following compounds are antiaromatic : [JEE Main 2012 (Online)]

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

O

(V) (VI)
+

(1) (III) and (VI) (2) (II) and (V) (3) (I) and (V) (4) (V) and (VI)
Ans. (4)
24. Among the following the molecule with the lowest dipole moment is : [JEE Main 2012 (Online)]
(1) CHCl3 (2) CH2Cl2 (3) CCl4 (4) CH3Cl
Ans. (3)

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25. The order of basicity of amines in gaseous state is :- [JEE (Main) - 2013]
(1) 3° > 2° > NH3 > 1° (2) 1° > 2° > 3° > NH3 (3) NH3 > 1° > 2° > 3° (4) 3° > 2° > 1° > NH3
Ans. (4)
26. Arrange the following compounds in order of decreasing acidity : [JEE (Main) - 2013]

OH OH OH OH

; ; ;

Cl CH3 NO2 OCH3

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

(1) II > IV > I > III (2) I > II > III > IV (3) III > I > II > IV (4) IV > III > I > II
Ans. (3)
27. The order of stability of the following carbocations : [JEE(Mains)-2013]

; ; is :

(1) III > II > I (2) II > III > I (3) I > II > III (4) III > I > II
Ans. (4)

28. Considering the basic strength of amines in aqueous solution, which one has the smallest pKb value?
[JEE MAIN-2014]
(1) (CH3)3 N (2) C6H5NH2 (3) (CH3)2NH (4) CH3NH2
Ans. (3)
29. The conjugate base of hydrazoic acid is :- [JEE (Main) - 2014]
(1) HN3– (2) N3– (3) N2– (4) N–3
Ans. (2)
30. Which one of the following compounds will not be soluble in sodium bicarbonate ? [JEE (Main) - 2014]
(1) Benzene sulphonic acid (2) Benzoic acid
(3) o-Nitrophenol (4) 2, 4, 6 - Trinitrophenol
Ans. (3)
31. Among the following oxoacids, the correct decreasing order of acid strength is : [JEE (Main) - 2014]
(1) HClO4 > HClO3 > HClO2 > HOCl (2) HClO2 > HClO4 > HClO3 > HOCl
(3) HOCl > HClO2 > HClO3 > HClO4 (4) HClO4 > HOCl > HClO2 > HClO3
Ans. (1)
32. In allene (C3H4), the type(s) of hybridization of the carbon atoms is (are) : [JEE Main 2014 (Online)]
(1) only sp2 (2) sp2 and sp (3) sp and sp3 (4) sp2 and sp3
Ans. (2)

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33. In which of the following pairs A is more stable than B. [JEE Main 2014 (Online)]
A B

(1) ,

(2) ,

(3) ,

(4) Ph3C , (CH3)3 C

Ans. (4)
34. Which one of the following substituents at para-position is most effective in stabilizing the phenoxide

O
ion? [JEE Main 2014 (Online)]

(1) – CH3 (2) – CH2OH (3) – OCH3 (4) – COCH3

Ans. (4)
35. Arrange the following amines in the order of increasing basicity. [JEE Main 2015 (Online)]

NH2 NH2 NH2

(1) < < < CH 3 NH 2

OCH3 NO2

NH2 NH2 NH2

(2) < < < CH 3 NH 2

OCH3 NO2

Page # 6
 NH2 NH2 NH2

(3) CH3NH2 < < <

OCH3 NO2

NH2 NH2 NH2

(4) < < < CH 3 NH 2

NO2 OCH3

Ans. (4)
36. The “N” which does not contribute to the basicity for the compound is : [JEE Main 2016 (Online)]

6 7
5 N
1N
8
2 N9
4
N H
3

(1) N 7 (2) N 9 (3) N 1 (4) N 3

Ans (2)
37. Which of the following compound is most reactive to an aqueous solution of sodium carbonate ?
[JEE Main 2017 (Online)]

(1) (2) (3) (4)

Ans. (3)
38. The increasing order of the boiling points for the following compounds is : [JEE Main 2017 (Online)]
C2H5OH C2H5Cl C2H5CH3 C2H5OCH3
(I) (II) (III) (IV)

(1) (IV) < (III) < (I) < (II) (2) (III) < (II) < (I) < (IV)
(3) (III) < (IV) < (II) < (I) (4) (II) < (III) < (IV) < (I)
Ans. (3)

Page # 7
39. Among the following compounds, the increasing order of their basic strength is : [JEE Main 2017 (Online)]

NH2 CH3
N
(I) (II) (III) (IV)
N NH2
H
(1) (II) < (I) < (III) < (IV) (2) (II) < (I) < (IV) < (III) (3) (I) < (II) < (IV) < (III) (4) (I) < (II) < (III) < (IV)
Ans. (2)
40. Which of the following compounds will show highest dipole moment ? [JEE Main 2017 (Online)]

O O
O

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

O

(1) (II) (2) (IV) (3) (III) (4) (I)

Ans. (4)
41. A mixture of containing the following four compounds is extracted with 1 M HCl. The compound that goes to
aqueous layer is : [JEE Main 2017 (Online)]

H
O
S N O

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

(1) (IV) (2) (II) (3) (I) (4) (III)

Ans. (2)

42. Which of the following molecules is least resonance stabilized ? [JEE - MAIN - 2017]

(1) (2) (3) (4)

O N O

Ans. (4)

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 JEE ADVANCED
Subjective Type Questions
1. Although phenoxide ion has more number of resonating structures than benzoate ion, benzoic acid is a stronger
acid than phenol. Why ? [IIT JEE - 1997]
Ans. Benzoate has equivalent resonating structures
2. Write resonating structure of the compound . [JEE-2003]

Ans.

3. Which one of the following two compounds is the stronger acid ? Explain why ? [JEE 2004]

I II
Ans. II is most acidic

4. Explain why 7-bromo-1, 3, 5-cycloheptatriene exist as an ion while 5-Bromo-1, 3-cyclopentadiene does not form any
ion even in the presence of Ag+ . Explain why ? [JEE 2004]

Ans. 7-bromo-1, 3, 5-cycloheptatriene on ionisation gives tropylium ion which is aromatic & highly stable, but

ionisation of 5-bromo-1, 3-cyclopentadiene gives 1, 3-cyclopentadienyl cation which is anti aromatic &
unstable. (non existent)
5. Explain the following observations [JEE 2005]

but not

Ans. In the formation of first product the antiaromaticity due to the presence of three “ ” rings of the reactant is
finished and the product becomes more stable.While in 2nd case the product is thermodynamically less stable.
6.

H3C CH3
N OCH2CH3 OH NO2
COOH
CH2OH

Page # 9
 OH CH2CH3 COOH
CH2CH3

N
H 3C CH3

Ans. (4)

7. The total number of contributing structures showing hyperconjugation (involving C–H bonds) for the following
carbocation is [JEE-11]

Ans. (6)
8. The total number of lone-pairs of electrons in melamine is [IIT - 2013]
Ans. 6
9. The number of resonance structures for N is [JEE(Advanced)-2015]
OH
NaOH
N

Ans. (9)
10. Among the following the number of aromatic compound(s) is [JEE(Advanced)-2017]

Ans. (5)
Single Objective Type Questions
11. Which one of the following has the smallest heat of hydrogenation per mole of H2 ? [IIT- 93]
(A) 1 – Butene (2) trans–2-–butene (3) cis–2–Butene (4) 1, 3–Butadiene
Ans. (D)
12. Most stable carbonium ion is [IIT - 95]
+ +
(A) p-NO2 C6H4 CH2 (2) C6H5 CH2
+ +
(C) p-Cl C6H4 CH2 (4) p-CH3O C6H4 CH2
Ans. (D)

Page # 10
13. In the following compounds [IIT JEE - 1996]
OH
OH OH OH

NO2 NO2
(I) CH3 (III) (IV)
(II)
The order of acidity is -
(A) III > IV > I > II (B) I > IV > III > II (C) II > I > III > IV (D) IV > III > I > II
Ans. (D)
14. Arrange the following compounds in order of increasing dipole moment : [IIT - 96]
(I) Toluene (II) m-dichloroobenzene
(III) o-dichlorobenzene (IV) p-dichlorobenzene
(A) I < IV < II < III (B) IV < I < II < III (C) IV < I < III < II (D) IV < II < I < III
Ans. (B)
15. The most unlikely representation of resonance structure of p-nitrophenoxide ion is - [IIT - 99]

+ + +
O N O +
O N O O N O O N O

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

O O O O

Ans. (C)
16. An aromatic molecule will not [IIT - 99]
(A) have 4n –  electrons (B) have (4n + 2) electrons
(C) be planar (D) by cyclic
Ans. (A)
17. Amongst the following, the most basic compound is - [IIT JEE - 2000]
(A) C6H5NH2 (B) p–NO2–C6H4NH2 (C) m–NO2–C6H4NH2 (D) C6H5CH2NH2\
Ans. (D)
18. The correct order of basicity of the following compound is : [IIT JEE - 2001]

NH O
CH3 C CH 3CH 2NH2 (CH 3)2NH CH3 C NH2
NH2
1 2 3 4

(A) 2 > 1 > 3 > 4 (B) 1 > 3 > 2 > 4 (C) 3 > 1 > 2 > 4 (D) 1 > 2 > 3 > 4
Ans. (B)
19. What is the acidity order of x, y & z ? [JEE-2003]

(A) x > y > z (B) x > z > y (C) y > z > x (D) z > y > x
Ans. (A)

Page # 11
20. Which of the following is least stable : [IIT - 2005]
+ +
(A) CH3 O CH CH HC CH 2 (B) CH3 O CH CH HC CH 2

+ +
(C) CH3 O CH CH HC CH 2 (D) CH3 O CH CH CH CH 2

Ans. (D)

21. A , The product A will be - [JEE-2007]

(A) (B)

(C) (D)

Ans. (A)

22. Among the following, the least stable resonating structure is : [JEE-2007]
 O
+
(A) (B) +
N

O


 O
+
(C) + N (D)
O

Ans. (A)

23. The correct stability order for the following species is : [JEE-2008]

(A) (II) > (IV) > (I) > (III) (B) (I) > (II) > (III) > (IV)
(C) (II) > (I) > (IV) > (III) (D) (I) > (III) > (II) > (IV)

Ans. (D)

Page # 12
24. Hyperconjugation involves overlap of the following orbitals : [JEE-08]
(A) – (B) –p (C) p – p (D)  – 
Ans. (B)
25. The correct stability order of the following resonating structures is : [JEE-09]

(A) (I) > (II) > (IV) > (III) (B) (I) > (III) > (II) > (IV)
(C) (II) > (I) > (III) > (IV) (D) (III) > (I) > (IV) > (II)
Ans. (B)
26. In the following carbocation; H/CH3 that is most likely to migrate to the positively charged carbon is
[JEE-09]

(A) CH3 at C-4 (B) H at C-4 (C) CH3 at C-2 (D) H at C-2
Ans. (D)
27. The correct acidity order of the following is : [IIT-JEE - 2009]

OH OH COOH COOH

Cl
CH3
(I) (II) (III) (IV)

(A) (III) > (IV) > (II) > (I) (B) (IV) > (III) > (I) > (II)
(C) (III) > (II) > (I) > (IV) (D) (II) > (III) > (IV) > (I)
Ans. (A)
28. Among the following compounds, the most acidic is [IIT-JEE - 2011]
(A) p-nitrophenol (B) p-hydroxybenzoic acid
(C) o-hydroxybenzoic acid (D) p-toluic acid
Ans. (C)
29. The compound that does NOT liberate CO2 on treatment with aqueous sodium bicarbonate solution, is
[IIT-JEE - 2013]
(A) Benzoic acid (B) Benzenesulphonic acid
(C) Salicyclic acid (D) Carbolic acid (phenol)
Ans. (D)
30. The hyperconjugative stabilities of tert-butyl cation and 2-butene, respectively, are due to
(A)  p (empty) and  * electron delocalisations. [JEE(Advanced)-2013]
(B)  * and   electron delocalisations.
(C)  p (filled) and   electron delocalisations.
(D) p (filled)  * and  * electron delocalisations.
Ans. (A)

Page # 13
31. The correct order of acidity for the following compounds is [JEE(Advanced)-2016]
CO2 H CO2H CO2H CO2H

HO OH OH

OH

I II
III OH IV

(A) I > II > III > IV (B) III > I > II > IV
(C) III > IV > II > I (D) I > III > IV > II
Ans. (A)
32. The order of basicity among the following compounds is [JEE(Advanced)-2017]

NH NH2
N NH HN N
H3C NH2 H 2N NH

I II III IV
(A) IV > II > III > I (B) II > I > IV > III (C) I > IV > III > I (D) IV > I > II > III
Ans. (D)
Multiple Choice Questions
33. Which of the following molecules, in pure form, is (are) unstable at room temperature ? [JEE-12]

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

Ans. (B, C)
34. Identify the binary mixtures (s) than can be separated into the individual compounds, by differential extraction,
as shown in the given scheme – [IIT-JEE - 2012]
NaOH (aq)
Compound 1 + Compound 2
Binary mixture containing
compound 1 and compound 2
NaHCO3 (aq)
Compound 1 + Compound 2
(A) C6H5OH and C6H5COOH (B) C6H5COOH and C6H5CH2OH
(C) C6H5CH2OH and C6H5OH (D) C6H5CH2OH and C6H5CH2COOH
Ans. (B, D)
35. Hydrogen bonding plays a central role in the following phenomena [IIT-JEE - 2014]
(A) Ice floats in water
(B) Higher Lewis basicity of primary amines than tertiary amines in aqueous solutions
(C) Formic acid is more acidic than acetic acid
(D) Demerisation of acetic acid in benzene
Ans. (A, B, D)
ASSERTION & REASON
36. Statement - I : p-Hydroxybenzoic acid has a lower boiling point that o-hydroxybenzoic acid.
Statement - II : o-Hydroxybenzoic acid has intramolecular hydrogen bonding. [IIT-JEE - 2003]
(A) Statement -I is True, Statement - II is True, Statement -II is a correct explanation for Statement - I.
(B) Statement -I is True, Statement - II is True, Statement -II is NOT a correct explanation for Statement - I.
(C) Statement -I is True, Statement - II is False.
(D) Statement -I is False, Statement - II is True.
Ans. (D)
MATCH THE COLUMN :
37. Match Ka values with suitable acid : [IIT-JEE - 2005]
Ka Acid

(A) 3.3 × 10–5 (p) COOH

(B) 4.2 × 10–5 (q) Me COOH

(C) 6.3 × 10–5 (r) Cl COOH

(D) 6.4 × 10–5 (s) MeO COOH

(E) 30.6 × 10–5 (t) O2N COOH

Ans. As;Bq;Cp;Dr ;Et

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