Type your textCC Type your te

CLIP CHEMISTRY CDP Type you

GENERAL ORGANIC CHEMISTRY C Type
CRR your
Typetext
yo
Type y
NAME: ____________________________________________ Type your
Typetext
your text
Batch: __________________
Type y

1. Write decreasing order of acidic strength of following compounds:

(i) (a) (b) (c) COOH

COOH COOH

COOH CH2 COOH

COOH
(ii) (a) (b) CH2 (c)
COOH COOH CH2 COOH

(iii) (a) CH4 (b) NH3 (c) H2O (d) H- F

(iv) (a) CH3COOH (b) CH3CH2OH (c) C6H5OH (d) C6H5SO3H

2. Write increasing order of basic strength of following:

(i) (a) R-NH2 (b) Ph – NH2 (c) R – CO – NH2

O
(ii) (a) (b) (c)
NH NH N
Me
3. Write decreasing order of acidic strength of following compounds:
O H O H O H O H
NO2 NO2 NO2 NO2
(i) (a) (b) (c) (d)

NO2 NO2
NO2

COOH COOH COOH

COOH
CH3 Cl Br
(ii) (a) (b) (iii) (a) (b)

4. Select the strongest acid in each of the following sets:

OH OH OH OH
NO2 NO2
(i) (a) (b) (c) (d)
NO2 NO2 NO2
NO2 NO2 NO2
5. Write decreasing order of basic strength of following:

(i) (a) CH3-C-NH2 (b) CH3-CH2-NH2 (c) CH3C-NH2 (d) NH2C-NH2

O NH2 NH NH

(ii) (a) (b) (c)

N N
H

FIITJEE Patna Centre, 2nd Floor, Saday Bhawan, Marwari Awas Complex, Fraser Road, Patna – 800 001, Ph. : 0612-3299798/ 99, 2205551 / 52
 CLIP CHEMISTRY CDP

GENERAL ORGANIC CHEMISTRY

6. Select the strongest base in following compound:

O S

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

N
N
N N
H
NH2 H H

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

NH N
N

N H

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

N N N N
H H H CH3 H Me
H
+ N N
N Li N
(iv) (a) (b) (c) (d)

7. Which one of the following is the most acidic?

(a) (b) (c) (d) CH2=CH-CH3

8. Which one of the following phenols will show highest acidity?

CH3 CH3
OH H 3C OH OH OH
H3C
(a) (b) (c) (d)
H3C
CH3 O2N H3C NO2
NO2
NO2 CH3
CH3 CH3
O Nb

9. Basicity order of N-atom in following comound is: H2N-C-CH

c
2 CH2-NH-C-CH3

N aH

N
CH3 d CH3

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

10. The correct pKa order of the following acids is:

HO OH O HO OH

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

(a) I > II > III (b) III > II > I (c) III > I > II (d) I > III > II
FIITJEE Patna Centre, 2nd Floor, Saday Bhawan, Marwari Awas Complex, Fraser Road, Patna – 800 001, Ph. : 0612-3299798/ 99, 2205551 / 52
 CLIP CHEMISTRY CDP

GENERAL ORGANIC CHEMISTRY

11. Which one of the following is least basic in character?

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

N N N

H H H

12. In each of the following pair of compounds, which is more basic in aqueous solution? Give an
explanation for your choice:
NH

(a) CH3NH2 or CF3NH2 (b) CH3CONH2 or H2N NH2

(c) n-PrNH2 or CH3CN (d) C6H5N(CH3)2 or 2,6-dimethyl – N , N - dimethylaniline

(e) m-nitroaniline or p-nitroaniline

13. Arrange the following compounds in order of increasing basicity.

(a) (1) CH3NH2 (2) CH3NH3 (3) CH3NH- (b) (1) CH3O- (2) CH3NH- (3) CH3CH2-

(c) (1) CH3CH = CH- (2) CH3CH2CH2- (3) CH3C C-

14. Compare the stability of the following compounds:

(I) (A) CH2 (B) CH3

O–
O O– O
– –
(II) (A) (B) (III) (A) CH3 C CH2 (B) H2C CH CH2
O

CD3 +
CH3
CH3 CH3 CD3 CD3 +
+ + N
(IV) (A) (B) (V) (A) | (B)
H
+ +
(VI) (A) HC  C − CH 2 − C H 2 (B) H 2 C = CH − CH 2 − C H 2

CH3 CH3 CD3 CD3

+ +
C C
(VII) (A) (B)
CH3 CD3
15. Compare acid strength of the following sets of compounds.
CO2H CO2H CO2H

(I) (A) CH3 (B) (C)

CH3
CH3
FIITJEE Patna Centre, 2nd Floor, Saday Bhawan, Marwari Awas Complex, Fraser Road, Patna – 800 001, Ph. : 0612-3299798/ 99, 2205551 / 52
 CLIP CHEMISTRY CDP

GENERAL ORGANIC CHEMISTRY

CO2H CO2H CO2H

OCH3
(II) (A) (B) (C)
OCH3
OCH3
CO2H CO2H CO2H
NO2
(III) (A) (B) (C)
NO2
NO2
16. Compare base strength of the following compounds:

NH2 NH2 NH2 NH2

NO2
(I) (A) (B) (C) (D)
NO2
NO2
CH3 CH3
(II) (A) CH3 C CH2 NH2 (B) CH3 Si CH2 NH2
CH3 CH3
O

NH2
(III) (A) CH3 C NH2 (B)
(Acetamide ) (Aniline)

NH CH3
(IV) (A) (B) C NH
NH2 C
CH3
NH2
Isopropyl imine
Guanidine

Et3N
(V) (A) (B) (VI) (A) (B)
Triethylamine
N N O N
| O
H
Quinuclidene

17. Identify the more stable form in the following resonance structures.

NH2 NH2 O O O
−
O
| |  || − || || |

(i) NH2 − C − NH2 and NH2 − C = NH2 (ii) CH3 − C− CH − C− CH3 and CH3 − C− CH = C− CH3
 (2) (1) (2)
(1)

O - -
O O
-
O +
(iii) (iv) H C OH and H C OH
and +
(1) (2)
-
(1) (2)

FIITJEE Patna Centre, 2nd Floor, Saday Bhawan, Marwari Awas Complex, Fraser Road, Patna – 800 001, Ph. : 0612-3299798/ 99, 2205551 / 52
 CLIP CHEMISTRY CDP

GENERAL ORGANIC CHEMISTRY

18. Write the stability order of following resonating structures:

(A) - (B) +
O O OCH 3 OCH 3

- +
N N NH2 NH2
(I) (II) (I) (II)

(C) - (D) +
O O

+
Cl Cl
(I) (II)

N N -
O O
O O
(I) (II)

19. Which of the following species are conjugated?

(A) (B) SH (C) CH2 = C = CH − NH2 (D) all of these

20. Which of the following pairs of structures is not a pair of resonating structures?
 
(A) H − C  NH; H − C = NH
(B) CH3CH = CHCH3 ; CH3CH2CH = CH2
(C) H3C C CH C CH3 ; H C C -
3 CH C CH3
-
O O O O
(D) +
;

21. Arrange the stability order for following compounds:

(I) CH2 = CH2 (II) CH3 − C = CH2 (III) CH2 = CH − CH = CH2
|
(IV) CH3 − CH = CH2
CH3

(V) CD3 − CH = CH2

22. Write the stability order of alkene by hyperconjugation:

(I) (II) CH3 − CH = CH − CH3

CH3 CH3
H CH 3
(III) C C (IV) H3C C CH CH C CH3

H3C CH 3 CH3 CH3

FIITJEE Patna Centre, 2nd Floor, Saday Bhawan, Marwari Awas Complex, Fraser Road, Patna – 800 001, Ph. : 0612-3299798/ 99, 2205551 / 52
 CLIP CHEMISTRY CDP

GENERAL ORGANIC CHEMISTRY

23. Write the stability order of following carbocations

(A) +

+ +

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


H3C + CH3
|
Ph
|

(B) CH3 − CH − C2H5 C CH 3 Ph − C − C2H5 Ph − C− C2H5

H3C  
(I) (III) (IV )
(II)

24. Following compound contains three C = C bond arrange in stability order:

H3C CH 3
b a
C C C C H
CH 3 CH 3
c H
H

25. Write the correct heat of hydrogenation order:

(I) (II)

(III) (IV)

ANSWERS

1. (i) c > b > a (ii) a > b > c (iii) d > c > b > a (iv) d > a > c > b
2. (i) c < b < a (ii) a < b < c 3. (i) d > c > a > b (ii) b > a (iii) b > a
4. (i) b 5. (i) d > c > b > a (ii) b > c > a 6. (i) d (ii) b
(iii) c (iv) a 7. b 8. b 9. b
10. b 11. a 12. (a) i (b) ii (c) i
(d) ii (e) I 13. (a) 2 < 1 < 3 (b) 1 < 2 < 3 (c) 3 < 1 < 2
14. (I) B > A (II) A > B (III) A > B (IV) B > A (V) A > B
(VI) B > A (VII) A > B 15. (I) A > B > C (II) A > B > C (III) A > C > B
16. (I) D > B > C > A (II) B > A (III) B > A (IV) A > B (V) A > B
(VI) B > A 17. (i) 2, (ii) 2, (iii) 1, (iv) 2 18. (A) I, (B) II, (C) I, (D) II
19. D 20. B 21. III > II > IV > V > I
22. I > III > II > IV 23. (A) III > II > IV > I (B) IV > III > II > I
24. b > a > c 25. III > IV > II > I

FIITJEE Patna Centre, 2nd Floor, Saday Bhawan, Marwari Awas Complex, Fraser Road, Patna – 800 001, Ph. : 0612-3299798/ 99, 2205551 / 52