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GOC combined - IIT-JAM Cemistry Questions

chemistry (Jadavpur University)

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ORGAN I C CH EM I ST RY
Daily Assignment
IIT-JAM
Home Work DPP

GOC (1)

1. Which of the following pairs do not constitute resonating structure

 O
Me  N  O and Me  O  N  O
O
(a) | (b) Me C and Me C
O
CH2 CH2

(c) and (d) Me–CH=CH–Me and MeCH2CH=CH2

O OH
2. Arrange the following resonating structures in the order of decreasing order of stability
  
CH 2  CH  Cl   C H 2  CH  Cl
 C H 2  CH  Cl 

3.
CHEM ACADEMY
I
(a) I > III > II
II
(b) II > I > III
III
(c) I > II > III
Compare the stability of the following pair of resonating structure
(d) III > II > I

 
(i) R  C  O 
R  C  O Me S Me
(ii) Me S Me
I II I II
O O

NH 2 NH 2
   
CH 2  N  N 
 C H2  N  N O O
(iii) (iv)
I II
I II

4. In which of the following compound all oxygen atom are sp2 hybridised.

H
O
O
O CH3
O O
(a) (b) (c) (d) O
H3C O O CH3
O O O
OH

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5. In which the following total  -electron is 12

H 2N NH2 H 2N NH2

(a) (b)
N N H3C O OCH3
O O

H3C S NH2
H 2N NH2

(c) OCH3 (d) MeO N OMe

H3C O S
CH3

6. In which of the nitrogen in sp2 hybridised

CH3 H
N N CH3
(a) (b) B
CH 3

(c) (d) N

7. CHEM ACADEMY
N

In which of the following oxygen atom is sp3 hybridised.

H

O O
(a) O O (b) BH (c) C (d) O O
O
H2
8. The most stable carbocation is

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

9. The most stable carbocation is

CH2
(a) (b) (c) (d)
O O O

10. The carbocation which is mesomeric stablize is/are

Me
N N
(a) (b) O Me (c) Me (d)
Me O
CH2
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11. The most stable carbocation is

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

CH3 CH3 CH3

12. The most stable carbocation is

OMe

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

O
OMe

13. The most stable carbocation is

CH 2 CH 2
CH 2 CH2
(a) (b) (c) (d)
NH2

14. CHEM ACADEMY

CH 3

The most basic site in the given compound is

NH 2

a b H
H 2N N

Nc Me

ANSWER KEY
1. a,c,d 2. c 3. (i) II > I (ii) I > II (iii) I > II (iv) II > I 4. a,c,d 5. c
6. a,b,c,d 7. c 8. c 9. c 10. c,d 11. a 12. d
13. d 14. a

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ORGAN I C CH EM I ST RY
Daily Assignment
IIT-JAM
Home Work DPP

GOC (2)

1. Number of atoms having sp2 hybridisation in the given compounds

N N
H H

N N
H
(a) 7 (b) 8 (c) 9 (d) 4
2. The most stable resonating structure for the given molecule
O Me

CHEM ACADEMY
H 2N

O Me OMe

(a) (b)
H2N H2N

OMe OMe

(c) H2N (d) H N

2

3. Among the following which is not represent pair of resonating structure

O
O H
N NH
(a) , (b) ,
H2N NH2 H2N NH2

O OH O O
(c) , (d) O , O

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4. In correct statement about the following molecule.

N N
N N
N
H
(a) It contain 4 sp2 atoms (b) It contains 6 electrons
(c) 4 nitrogen contain localised lone pairs (d) 2 nitrogen contain delocalised lone pairs.
5. How many  electrons present in the given molecule.
S

6. How many atoms are sp2 hybridised

H
O N
HO
Me H
O N N

H H

O O

CHEM ACADEMY
O
C C C
7. H OH 
 H OH 
 H OH
I II III

Among these canonical structures, the correct order of stability is

(a) I > II > III (b) III > II > I (c) I > III > II (d) II > I > III
8. Arrange the following which is most stabilised cation?

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

9. (I) CH 3  O  CH  CH  CH  CH 2
 
(II) CH 3  O  C H  CH  CH  C H 2

 
(III) CH 3  O  CH  CH  CH  C H 2

Among these three canonical structures (through more are possible) what would be their relative
contribution in the hybrid
(a) I > II > III (b) III > II > I (c) I > III > II (d) III > I > II

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10. 
 
 
 

N N N N N
I V
II III IV

Among these canonical structures of pyridinie, the correct order of stability is

(a) (I = V) > (II = IV) > III (b) (II = IV) > (I = V) > III
(c) (I = V) > III > (II = IV) (d) III > (II = IV) > (I = V)
11. In which of the following pairs, first species is more stable than second?

O
||
(a) CH 3  CH 2 O  or CH 3CO 

O O O O
||  || ||  ||
(b) CH 3C C HCH 2CH or CH3C C HCH3

CHEM ACADEMY
(c) CH 3 C

HCH 2
O
||
CCH 3 or CH 3 CH 2

C
O
||
HCCH 3

O O

N– N–
(d) or
O
12. Which of the following has longest C – O bond:

O O O O
(a) (b) (c) (d)

CH2
13. Which of the following carbocation will be more stable?

(a) (b)

(c) (d)

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14. Which of the following is incorrect relation between given pairs?

NH 2 NH2 O OH

(a) = Resonance (b) = Tautomers

R O R O
S S R R
(c) = Resonance (d) O O = Tautomers
H H H
H
15. Which of the following pair represents non identical pair?

(a) (b)

(c) (d)

16. The correct stability order of the following resonance structures is:

17.
CHEM ACADEMY
(a) I > II > IV > III (b) I > III > II > IV
Which of the following cations is most stable
(c) II > I > III > IV (d) III . I > IV > II

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

ANSWER KEY
1. c 2. b 3. c 4. a,d 5. 8 6. 9 7. c
8. c 9. c 10. a 11. d 12. b 13. a 14. d
15. d 16. b 17. c

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ORGAN I C CH EM I ST RY
Daily Assignment
IIT-JAM
Home Work DPP

GOC (3)

1. The group which is/are +M in nature

 
(a)  CH 2 (b)  NR 3 (c)  NR 2 (d) –OCOCH3
2. Arrange the order of +M group as increasing order of their strength

(a)  N H 2  F  OCH   Br (b) OCH 3  OH   NH 2   F
3


(c)  N H 2  OH  OCH3   F (d) OCOCH3  OCH 3   OH   F

3. Arrange the group in increasing order of their +M strength

(a) OPh  OCH 3  OH (b) OCH 3  OH  OPh

4. CHEM ACADEMY
(c) OH  OPh  OCH3
The group which is/are –M in nature

(d) OH  OCH 3  OPh


(a)  BR 2 (b)  PR 3 (c)  NR 3 (d) SR

5. The most electron rich alkene is

(a) OCH3 (b) NPh2 (c) NH2 (d) F
6. The correct order of alkene towards reactivity of electrophile

(I) (II) (III) N (IV) B

O O O
H H
(a) III > II > I > IV (b) III > IV > I > II (c) III > I > II > IV (d) IV > III > II > I
7. The correct order ofthe reactivity of alkene towards electrophile
CH3 O CH3
O
(P) (Q)
O

O O
CH 3 H
(R) (S)

(a) S > R > P > Q (b) S > P > R > Q (c) R > S > Q > P (d) S > R > Q > P

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8. The correct order reactivity of benzene ring towards electrophile

SH NH2 O CH 3

(P) (Q) (R) (S)

(a) Q > P > R > S (b) Q > R > P > S (d) P > Q > R > S (d) S > Q > P > R
9. The most reactive benzene ring towards electrophile
OCH3 OH O CH 3 O COCH 3

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

10. In which of the following, 2nd ring is more electron rich

O O
II N C O
(a) (b)
I H II
I
O H2
H2
O C C S C P

CHEM ACADEMY
(c) (d)
I R II
I II
11. The most stable carbocation is

O OCOCH3 OPh OCH3

(a) (b) (c) (d)
CH3
12. The correct order of the stability of carbocation is

(P) (Q) (R) (S) N

O O O CH3
(a) P > R > Q > S (b) S > R > Q > P (c) S > P > R > Q (d) S > R > P > Q
13. The correct order of the stability of carbocation is

CH2 CH2 CH2

CH2
(P) (Q) (R) (S)

OCH3 OH NH2

(a) P > Q > R > S (b) Q > R > S > P (c) S > Q > R > P (d) S > R > Q > P

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14. The correct order of the stability of carbocation

CH2 CH2 CH2

CH2
(P) (Q) (R) (S)

OCOCH 3 OH OCH3
(a) Q > R > P > S (b) R > P > Q > S (c) R > P > S > Q (d) P > R > Q > S
15. The correct order of the stability of carbocation
O
(P) OCH3 (Q)
O

CH3
(R) CH3 (S) N
O
H
(a) R > P > Q > S (b) S > R > Q > P (c) S > Q > R > P (d) S > R > P > Q
16. The correct order of reactivity of carbonyl compound is
O O O
H

CHEM ACADEMY
(P) (Q) O (R) N

(a) P > R > Q (b) P > Q > R (c) R > P > Q (d) Q > P > R
17. The correct order of reactivity of the carbonyl groups
O
O O CH3 O O
(P) (Q) (R) N (S) (T)
H O CH3 O H
H
(a) P > Q > R > S > T (b) P > Q > S > R > T (c) P > Q > T > S > R (d) P > Q > S > T > R
18. The correct order of the reactivity
O O O O O O
(P) CH3 (Q) (R) H (S) (T)
O O O NHCH3
(a) P > Q > R > S > T (b) Q > P > R > T > S (c) T > Q > P > R > S (d) R > P > Q > S > T
19. The correct order of reactivity of the carbonyl groups
O
O O H3C CH3 O
(P) H3C CH3 (Q) CH3 (R) N N (S)
O O O
H H
(a) Q > P > R > S (b) S > Q > P > R (c) R > S > P > Q (d) S > Q > R > P
ANSWER KEY
1. a,c,d 2. c 3. d 4. a,b,d 5. c 6. c 7. d
8. b 9. c 10. d 11. d 12. d 13. d 14. c
15. b 16. b 17. d 18. c 19. b

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ORGAN I C CH EM I ST RY
Daily Assignment
IIT-JAM
Home Work DPP

GOC (4)
1. The most reactive benzene ring towards electrophile
O
NO2
O OCH3 O NMe2
O CH 3
(a) (b) (c) (d)

2. In which of the following I ring in more reactive than II ring towards electrophile
H2 O
(a) N C O (b) C O
H
O H O H2 O
(c) C N (d) C O C C

3.

CHEM ACADEMY
The most stable carbanion is
  
(a) C H 2  CH 3 (b) C H 2  F (c) C H 2  OCH 3 (d) C H 2  Cl
4. The most stable carbanion is

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

O O S S
5. The most stable carbanion is
S
S S O
(a) (b) (c) (d)
S S S O
6. The most stable carbanion is

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

NH3 PR3 NR3 PR3
7. The most stable carbanion is

H H2 H2
(a) C Cl (b) CH2 (c) C CH2 (d) C CH
Cl

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8. The least reactive alkene towards electron deficient species.

O O O N
(a) (b) (c) (d)
O O
9. The most stable carbanion is

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

PPh3 NMe3 CH3 PPh3
10. The most stable carbanion is
   
(a) C H 3 (b) C(OMe)3 (c) C F3 (d) C Cl3

ANSWER KEY
1. d 2. a,d 3. d 4. d 5. c 6. b 7. a
8. a 9. d 10. d

CHEM ACADEMY

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ORGAN I C CH EM I ST RY
Daily Assignment
IIT-JAM
Home Work DPP

GOC (5)
1. Correct order of stability of carbocation

(P) (Q) (R) (S)

(a) Q > R > P > S (b) S > Q > P > R (c) R > Q > P > S (d) R > Q > S > P
2. Correct order of stability of carbocation

(P) (Q) (R) (S)

(a) P > Q > R > S (b) S > P > Q > R (c) S > P > R > Q (d) R > S > Q > P
3. Correct order of heat of hydrogenation

(P)
CHEM ACADEMY
(a) P > Q > R > S
(Q)

(b) Q > R > S > P

(R)

(c) Q > R > P > S

(S)

(d) S > P > R > Q

4. Highest heat of hydrogenation

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

5. Correct order of stability of carbocation

CH 2 CH 2
CH2 CH2

(P) (Q) (R) (S)

CH 3 CH 3
(a) R > Q > P > S (b) Q > P > R > S (c) Q > R > S > P (d) Q > S > R > P
6. Correct order of reactivity of aromatic ring towards electrophile
CH 3
CH 3

(P) (Q) (R) (S)

CH 3
(a) P > Q > S > R (b) P > Q > R > S (c) R > Q > P > S (d) P > R > Q > S

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7. Correct order of stability of alkene

(P) (Q) (R) (S)

(a) P > Q > S > R (b) P > R > Q > S (c) Q > P > R > S (d) P > Q > R > S
8. Compre the stability of given compound

(P) (Q) (R)

(a) P > Q > R (b) Q > R > P (c) Q > P > R (d) R > Q > P
9. Compare the stability of following carbocation

H3C C CH3 D3C C CD3 T3C C CT3

(P) (Q) (R)
CH3 CD3 CT3
(a) P > Q > R (b) P > R > Q (c) Q > P > R (d) Q > R > P
10. Compare the stability of carbon free radicals

(P) (Q) (R) (S)

(a) P > R > S > Q (b) P > Q > R > S (c) Q > P > R > S (d) R > Q > P > S

CHEM ACADEMY ANSWER KEY

1. d 2. c 3. a 4. a 5. c 6. b 7. a
8. b 9. a 10. b

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